4-Nitro-1,2-benzenediol by Asch

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Date

80 reactions in Reaxys

2017-10-26 10h:12m:27s (EST)

80 reactions in Reaxys

2017-10-26 10h:14m:01s (EST)

1. Query

O N

Search as: As drawn 2. Query

(1. Query) AND itemno in (1)

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O O

Rx-ID: 271036 View in Reaxys 1/80 Yield 21 %

Conditions & References Hydroxychavicol (4-Allylbenzene-1,2-diol, 2); General Procedure General procedure: To a suspension of AlI3 (5.5 mmol, 1.1 equiv) in hot CH3CN (40 mL) were added sequentially DIC (0.379 g, 3 mmol, 0.6 equiv) and eugenol (1, 0.821 g, 5.0 mmol). The mixture was stirred for 18 h at 80 °C, and then it was cooled to r.t., acidified with HCl (2 mol/L, 10 mL), and extracted with EtOAc (3 × 50 mL). The organic phases were combined, washed with sat. aq Na2S2O3 (10 mL) and brine (10 mL), and was dried (MgSO4). The solvent was removed on a rotary evaporator and the residue was purified by flash column chromatography (PE/ EtOAc, 4:1) to afford 2 (0.750 g, 99percent) as a white solid With aluminium(III) iodide, diisopropyl-carbodiimide in acetonitrile, Time= 18h, T= 80 °C Sang, Dayong; Wang, Jiahui; Zheng, Yun; He, Jianyuan; Yuan, Caili; An, Qing; Tian, Juan; Synthesis (Germany); vol. 49; nb. 12; (2017); p. 2721 - 2726 View in Reaxys

21 %

44 :To a 100 ml eggplant flask were added aluminum triiodide (2.251 g), acetonitrile (40 ml) A mixture of DIC (0.375 g) and 4-nitro-2-methoxyphenol (0.848 g) was heated to 80 ° C, After stirring for 18 hours, the mixture was stirred, cooled to room temperature and then acidified with 2 mol / L dilute hydrochloric acid (10 ml) And extracted with ethyl acetate (50 ml X). The combined organic phases were washed first with a saturated aqueous solution of sodium thiosulfate (10 ml), washed with saturated brine (10 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated Instrument evaporated, The residue was purified by flash column chromatography (eluent: ethyl acetate / petroleum ether = 3: 7, volume ratio) To give 0.165 g of 4-niro catechol (yellow solid in 21percent yield). Along = 0.80 (petroleum ether / ethyl acetate = 1: 1, volume ratio). With aluminium(III) iodide, diisopropyl-carbodiimide in acetonitrile, Time= 18h, T= 80 °C Patent; Jingchu Institute Of Technology; Sang Dayong; Tian Juan; (19 pag.); CN106866377; (2017); (A) Chinese View in Reaxys With hydrogen bromide Cardwell; Robinson; Journal of the Chemical Society; vol. 107; (1915); p. 258 View in Reaxys OH

O N O

O N

Rx-ID: 116647 View in Reaxys 2/80 Yield 61 %

Conditions & References With sodium dihydrogenphosphate, Time= 0.25h, T= 25 °C , pH= 7, Glovebox Dhammaraj, Taweesak; Phintha, Aisaraphon; Pinthong, Chatchadaporn; Medhanavyn, Dheeradhach; Tinikul, Ruchanok; Chenprakhon, Pirom; Sucharitakul, Jeerus; Vardhanabhuti, Nontima; Jiarpinitnun, Chutima; Chaiyen, Pimchai; ACS Catalysis; vol. 5; nb. 8; (2015); p. 4492 - 4502 View in Reaxys With potassium peroxomonosulphate Patent; Chem. Fabr. Schering; DE81298; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 4; p. 121 View in Reaxys With caro's acid Bamberger; Czerkis; Journal fuer Praktische Chemie (Leipzig); vol. <2> 68; (1903); p. 480 View in Reaxys With water, (γ-irradiation)

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Graesslin,D. et al.; Chemische Berichte; vol. 100; (1967); p. 3077 - 3083 View in Reaxys With dihydrogen peroxide in acetonitrile, Irradiation Omura,K.; Matsuura,T.; Tetrahedron; vol. 26; (1970); p. 255 - 265 View in Reaxys With tetrahydroboratocopper(I) complex 4, oxygen, 1) THF, 1 h, 25 deg C 2) 18 h, 40 deg C, Yield given. Multistep reaction Chioccara, Francesco; Gennaro, Patricia Di; Monica, Girolamo La; Sebastiano, Roberto; Rindone, Bruno; Tetrahedron; vol. 47; nb. 25; (1991); p. 4429 - 4434 View in Reaxys With tetrachloromethane in water, Time= 1.5h, T= 25 °C , sonication, Degradation, Kinetics Hua, Inez; Hoffmann, Michael R.; Environmental Science and Technology; vol. 30; nb. 3; (1996); p. 864 - 871 View in Reaxys With D-glucose 6-phosphate, glucose 6-phosphate dehydrogenase, Time= 0.333333h, T= 37 °C , Enzyme kinetics, Further Variations: Reagents Hanioka, Nobumitsu; Yamamoto, Maki; Iwabu, Hiroyuki; Jinno, Hideto; Tanaka-Kagawa, Toshiko; Naito, Shinsaku; Shimizu, Takefumi; Masuda, Kazufumi; Katsu, Takashi; Narimatsu, Shizuo; Life Sciences; vol. 81; nb. 19-20; (2007); p. 1436 - 1445 View in Reaxys With D-glucose 6-phosphate, nicotinamide adenine dinucleotide phosphate, glucose 6-phosphate dehydrogenase, yeast cells expressing human monkey CYP2E1, Time= 0.333333h, T= 37 °C , Enzyme kinetics, Further Variations: Catalysts Hanioka, Nobumitsu; Yamamoto, Maki; Iwabu, Hiroyuki; Jinno, Hideto; Tanaka-Kagawa, Toshiko; Naito, Shinsaku; Shimizu, Takefumi; Masuda, Kazufumi; Katsu, Takashi; Narimatsu, Shizuo; Life Sciences; vol. 81; nb. 19-20; (2007); p. 1436 - 1445 View in Reaxys With hydrogenchloride, human P450 2E1 isoenzyme, NADP, magnesium chloride, Time= 0.333333h, T= 37 °C , aq. phosphate buffer, Enzymatic reaction, Kinetics Dai, Jieyu; Zhang, Fan; Zheng, Jiang; Chemico-Biological Interactions; vol. 183; nb. 1; (2010); p. 49 - 56 View in Reaxys Stage 1: With dipotassium peroxodisulfate, potassium hydoxide Stage 2:Acidic conditions Iga, Dumitru Petru; Silvia; Nicolescu, Alina; Chira, Nicoleta-Aurelia; Revue Roumaine de Chimie; vol. 55; nb. 5; (2010); p. 357 - 363 View in Reaxys With styrene, recombinant human cytochrome P450 2E1 Supersomes®, water, NADPH in methanol, aq. phosphate buffer, T= 37 °C , pH= 7.4, Enzymatic reaction, Reagent/catalyst Hartman, Jessica H.; Boysen, Gunnar; Miller, Grover P.; Xenobiotica; vol. 43; nb. 9; (2013); p. 755 - 764 View in Reaxys Reaction Steps: 3 1: potassium carbonate / acetonitrile / |Sealed tube; |Reflux 2: [(η6-p-MeC6H4Pri)2Ru2Cl2(μ-Cl)2]; trifluoroacetic acid; trifluoroacetic anhydride; [bis(acetoxy)iodo]benzene / 8 h / 80 °C / |Sealed tube 3: hydrazine hydrate / 8 h / 20 °C / |Sealed tube With [(η6-p-MeC6H4Pri)2Ru2Cl2(μ-Cl)2], [bis(acetoxy)iodo]benzene, potassium carbonate, hydrazine hydrate, trifluoroacetic acid, trifluoroacetic anhydride in acetonitrile Yang, Xinglin; Sun, Yonghui; Chen, Zhang; Rao, Yu; Advanced Synthesis and Catalysis; vol. 356; nb. 7; (2014); p. 1625 - 1630

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View in Reaxys Enzyme Assay Protocol Reactions were performed intriplicate at the specified pH in 100 mM KPi at 25 °C. Bufferedsolutions (total reaction volume 250 μL) of DHP (10 μM finalconcentration) and substrate (500 μM final concentration)were premixed, and then the reaction was initiated uponaddition of H2O2 (50, 100, 250, 500, or 1000 μM finalconcentrations). Experiments were performed in the presenceof D-mannitol (500 μM), superoxide dismutase (SOD) (∼2 U/μL), DMSO (10percent v/v). For the studies with sodium formate, abuffered solution (100 mM KPi; 500 μM sodium formate) at pH 6 was utilized. After 5 min, reactions were quenched withexcess catalase. A 100 μL aliquot of reaction sample was diluted10-fold with 900 μL of 100 mM KPi at the reaction pH. Dilutedsamples were analyzed using a Waters 2796 BioseparationsModule coupled with a Waters 2996 photodiode array detector,and equipped with a Thermo-Scientific ODS Hypersil (150mm × 4.6 mm) 5 μm particle size C18 column. Separation ofobserved analytes was performed using a linear gradient ofbinary solvents (solvent A - H2O containing 1percent trifluoroaceticacid: solvent B MeCN). Elution was performed using thefollowing conditions: (1.5 mL/min A:B) 95:5 to 5:95 linearlyover 4 min; 5:95 isocratic for 1 min; 5:95 to 95:5 linearly over 1min, then isocratic for 7 min. Data analysis was performedusing the Empower software package (Waters Corp.).Calibration curves for all nitrophenols were performed usingserial dilutions of commercially available analytes to determinethe amount of substrate conversion. With dihydrogen peroxide, sodium formate in aq. phosphate buffer, Time= 0.0833333h, T= 25 °C , pH= 6, Glovebox, Inert atmosphere, Reagent/catalyst, pH-value McCombs, Nikolette L.; D'Antonio, Jennifer; Barrios, David A.; Carey, Leiah M.; Ghiladi, Reza A.; Biochemistry; vol. 55; nb. 17; (2016); p. 2465 - 2478 View in Reaxys O O

OH O

O N

Rx-ID: 169519 View in Reaxys 3/80 Yield

Conditions & References With aluminum tri-bromide, nitrobenzene, T= 0 °C Mosettig; Burger; Journal of the American Chemical Society; vol. 52; (1930); p. 2988,2992 View in Reaxys 3 : Example 3 Oxidation of 4-Nitrobenzodioxole Peroxygenases oxidizes 4-nitrobenzodioxole (1,2-(Methylenedioxy)-4-nitrobenzene) to 4-nitrocatechol in presence of hydrogen peroxide and the produced yellow color is quantified spectrophotometrically at 425 nm (ε425=9,700M−1 cm −1).

(0250) A 10 mM stock solution of 4-nitrobenzodioxole (98percent pure, 161500 Aldrich) was prepared in acetonitrile. The final reaction mixture (0.2 ml) contained 1.0 mM 4-nitrobenzodioxole, 10percent acetonitrile, buffer (50 mM phosphate buffer pH 7 or 50 mM Britton-Robinson buffer pH 4), 20 μl peroxygenase fermentation supernatant (see Example 1) and 0.5 mM hydrogen peroxide. (0251) The reaction was started by adding the peroxygenase supernatant to the other ingredients used in the assay. A SpectraMax microtitre plate reader from Molecular Devices was applied to monitor the change in absorbance at 425 nm in a 96 well microtitre plate at room temperature. Blanks prepared without addition of enzyme were included. With peroxygenase, dihydrogen peroxide in aq. phosphate buffer, acetonitrile, pH= 7, Enzymatic reaction, pH-value Patent; Novozymes A/S; Landvik, Sara; Oestergaard, Lars H.; Kalum, Lisbeth; (25 pag.); US9382559; (2016); (B2) English View in Reaxys 3 : Example 3 Oxidation of Nitrobenzodioxole Example 3 Oxidation of Nitrobenzodioxole (0294) Peroxygenases oxidize nitrobenzodioxole (1,2-(Methylenedioxy)-4nitrobenzene) to nitrocatechol in the presence of hydrogen peroxide and the produced yellow color is quantified spectrophotometrically at 425 nm (ε425=9,700 M−1 cm−1). (0295) A 10 mM stock solution of nitrobenzodioxole (98percent pure, 161500 Aldrich) was prepared in acetonitrile. The final reaction mixture (0.2 ml) contained 1.0 mM nitrobenzodioxole, 10percent acetonitrile, 20 μl peroxygenase fermentation supernatant (see Example 1), 0.5 mM hydrogen peroxide, and 50 mM phosphate buffer pH 7. (0296) The reaction was started by adding the peroxygenase fermentation supernatant to the other ingredients used in the assay. A SpectraMax microtitre plate reader from Molecular Devices was applied to monitor the change in absorbance at 425 nm in a 96 well microtitre plate at room temper-

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ature. Blanks prepared without addition of enzyme were included. (0297) The increase in absorbance was recorded over 5 minutes and the results are shown in Table 3 as change in absorbance (milli Abs) pr. minute. [table-us-00004en] TABLE 3 Sample Rate (mA/min) at pH 7 Blank −1.1 Peroxygenase from Example 1 35.8 With dihydrogen peroxide in aq. phosphate buffer, acetonitrile, pH= 7, Enzymatic reaction, Catalytic behavior Patent; Novozymes A/S; Landvik, Sara; Oestergaard, Lars Henrik; Kalum, Lisbeth; (25 pag.); US9404093; (2016); (B2) English View in Reaxys

O N HO

Rx-ID: 619917 View in Reaxys 4/80 Yield

Conditions & References With potassium nitrite, sulfuric acid, water Benedikt; Chemische Berichte; vol. 11; (1878); p. 362 View in Reaxys durch Nitrierung Meulenhoff; Recueil des Travaux Chimiques des Pays-Bas; vol. 44; (1925); p. 163 View in Reaxys Weselsky; Benedikat; Monatshefte fuer Chemie; vol. 3; (1882); p. 387 View in Reaxys With sodium peroxynitrite, sodium hydrogencarbonate in water-d2, Time= 0.166667h, pH= 7.0, Product distribution, Further Variations: Reagents Nonoyama, Nobuaki; Oshima, Hiroshi; Shoda, Chizuru; Suzuki, Hitomi; Bulletin of the Chemical Society of Japan; vol. 74; nb. 12; (2001); p. 2385 - 2395 View in Reaxys Reaction Steps: 3 1: aqueous sodium carbonate-solution; sodium dithionite 2: aqueous nitric acid; acetic acid / 30 - 35 °C 3: ethanolic KOH With potassium hydroxide, sodium dithionite, nitric acid, sodium carbonate, acetic acid Barton; Linnell; Senior; Quarterly Journal of Pharmacy and Pharmacology; vol. 18; (1945); p. 41,43 View in Reaxys Reaction Steps: 3 1: K2CO3; acetone 2: acetic acid; aqueous HNO3 3: concentrated aqueous HCl; acetic acid With hydrogenchloride, nitric acid, potassium carbonate, acetic acid, acetone Baker; Kirby; Montgomery; Journal of the Chemical Society; (1932); p. 2876,2878 View in Reaxys With tert.-butylnitrite in acetonitrile, T= 29.84 °C , Kinetics, Solvent, Temperature Kumar, M. Satish; Rajanna; Venkateswarlu; Rao, K. Lakshman; International Journal of Chemical Kinetics; vol. 48; nb. 4; (2016); p. 171 - 196 View in Reaxys

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OH O HO

S O

O N

Rx-ID: 8620005 View in Reaxys 5/80 Yield

Conditions & References With recombinant human steroid sulfatase, water, pH= 7.5, Hydrolysis, Enzyme kinetics Bilban, Melitta; Billich, Andreas; Auer, Manfred; Nussbaumer, Peter; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 9; (2000); p. 967 - 969 View in Reaxys With hydrogenchloride in water, T= 90 °C Sager, Jennifer E.; Choiniere, John R.; Chang, Justine; Stephenson-Famy, Alyssa; Nelson, Wendel L.; Isoherranen, Nina; ACS Medicinal Chemistry Letters; vol. 7; nb. 8; (2016); p. 791 - 796 View in Reaxys O

O HO O

NH 2 N N

O N

OH O

Rx-ID: 42398490 View in Reaxys 6/80 Yield

Conditions & References in isopropyl alcohol, Irradiation, Mechanism Hinks, Mallory L.; Brady, Monica V.; Lignell, Hanna; Song, Mijung; Grayson, James W.; Bertram, Allan K.; Lin, Peng; Laskin, Alexander; Laskin, Julia; Nizkorodov, Sergey A.; Physical Chemistry Chemical Physics; vol. 18; nb. 13; (2016); p. 8785 - 8793 View in Reaxys

OH O

O O

O N

HO O

OH O

Rx-ID: 43933920 View in Reaxys 7/80 Yield

Conditions & References With dihydrogen peroxide in water, Time= 24h, T= 50 °C , pH= 3, Reagent/catalyst Martin-Martinez, Maria; Ribeiro, Rui S.; Machado, Bruno F.; Serp, Philippe; Morales-Torres, Sergio; Silva, Adrián M. T.; Figueiredo, José L.; Faria, Joaquim L.; Gomes, Helder T.; ChemCatChem; vol. 8; nb. 12; (2016); p. 2068 - 2078 View in Reaxys

O N

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O O

O N

OH O

Rx-ID: 43933921 View in Reaxys 8/80 Yield

Conditions & References With dihydrogen peroxide in water, Time= 24h, T= 50 °C , pH= 3 Martin-Martinez, Maria; Ribeiro, Rui S.; Machado, Bruno F.; Serp, Philippe; Morales-Torres, Sergio; Silva, Adrián M. T.; Figueiredo, José L.; Faria, Joaquim L.; Gomes, Helder T.; ChemCatChem; vol. 8; nb. 12; (2016); p. 2068 - 2078 View in Reaxys O N

O N

HO HO

OH O

Rx-ID: 44455561 View in Reaxys 9/80 Yield

Conditions & References 2.5. Photocatalytic degradation of DNBP Photocatalytic degradation of DNBP was performed in a XPA‐7 photochemical reactor (Xujiang Electromechanical Plant, Nanjing, China). Cylindrical quartz photochemical reactors of 22 cm x 2 cm (height x diameter) were vertically placed at a fixed distance (3.5 cm) from a 500 W Xenon lamp (Institute of Electric Light Source, Beijing) as light source to mimic solar irradiation. For the irradiation experiments, an aqueous solution of DNBP (40 mL) and the photocatalyst were added to the photoreactor. The resultant mixture was stirred continuously in the dark for at least 2 h to ensure the adsorption/desorptionequilibrium of DNBP was established. The suspensions werethen irradiated by the xenon lamp with the transmission of wavelengths below 380 nm limited using glass filters, while continuous purging the reactor with air. Aliquots were withdrawn at specific time intervals during the degradation experiments and analyzed after centrifugation for 5 min at 3000 r/min to completely remove any solid particles. The filtrates were subjected to UV‐visible spectrophotometric analysis tomonitor the concentration of DNBP at various time intervals at a wavelength of 271 nm [24]. The mineralization of DNBP was monitored by measuring the total organic carbon (TOC) with an Elementary Analyzer (Multi N/C 2100S, Analytikjena) by direct injection of the aqueous solution after the photocatalysis reaction. The GC/MS system (Agilent 6890 GC and 5793 MS) was used to identify the intermediate products formed during the photooxidative process. The carrier gas flow rate was 0.5mL/min and the oven temperature was programmed as follows: isothermal at 40 °C for 5 min, from 40 to 280 C at 5 °C/min, and isothermal at 280 °C for 1 min. With TiO2 nanoparticles loaded on silica-alumina aerogels from industrial fly ash in water, Time= 5h, T= 40 - 280 °C , pH= 4.86, UV-irradiation, Kinetics, Reagent/catalyst, Concentration Wang, Hui-Long; Qi, Hui-Ping; Wei, Xiao-Na; Liu, Xiao-Yu; Jiang, Wen-Feng; Chinese Journal of Catalysis; vol. 37; nb. 11; (2016); p. 2025 - 2033 View in Reaxys

O N O

Rx-ID: 2985740 View in Reaxys 10/80 Yield 90 %

Conditions & References With dihydrogen peroxide in water, Time= 3h, T= 20 °C , Green chemistry, Dakin Phenol Oxidation Saikia, Bishwajit; Borah, Parinita; RSC Advances; vol. 5; nb. 128; (2015); p. 105583 - 105586 View in Reaxys

75 %

With 7,8-dichloro-1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine, dihydrogen peroxide, sodium hydrogencarbonate in methanol, water, Time= 0.166667h, T= 20 °C , Dakin oxidation

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Chen, Shuai; Hossain, Mohammad S.; Foss, Frank W.; Organic Letters; vol. 14; nb. 11; (2012); p. 2806 - 2809 View in Reaxys 65 %

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, 1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine, oxygen, sodium hydrogencarbonate in water, acetonitrile, Time= 3h, T= 20 °C , Dakin Phenol Oxidation Chen, Shuai; Foss, Frank W.; Organic Letters; vol. 14; nb. 19; (2012); p. 5150 - 5153,4 View in Reaxys

60 %

With sodium percarbonate in tetrahydrofuran, water, Time= 7h, ultrasonication Kabalka, G. W.; Reddy, N. K.; Narayana, C.; Tetrahedron Letters; vol. 33; nb. 7; (1992); p. 865 - 866 View in Reaxys OH

O N

Rx-ID: 11148578 View in Reaxys 11/80 Yield

Conditions & References

95 %

With hydrogen peroxide, Time= 1h, T= 20 °C , Green chemistry, Dakin Phenol Oxidation Saikia, Bishwajit; Borah, Parinita; Barua, Nabin Chandra; Green Chemistry; vol. 17; nb. 9; (2015); p. 4533 4536 View in Reaxys

83 %

With urea-hydrogen peroxide, Time= 0.416667h, T= 85 °C , Dakin reaction Varma, Rajender S.; Naicker, Kannan P.; Organic Letters; vol. 1; nb. 2; (1999); p. 189 - 191 View in Reaxys O

O N

OH HO

Rx-ID: 39761752 View in Reaxys 12/80 Yield

Conditions & References With dihydrogen peroxide, Time= 0.1h, T= 69.84 °C , pH= 6, Microwave irradiation, Catalytic behavior, Concentration, pH-value Pan, Weiqian; Zhang, Guangshan; Zheng, Tong; Wang, Peng; RSC Advances; vol. 5; nb. 34; (2015); p. 27043 27051 View in Reaxys OH O

O O

Rx-ID: 37873332 View in Reaxys 13/80 Yield

Conditions & References

65 %

With hydrazine hydrate, Time= 8h, T= 20 °C , Sealed tube Yang, Xinglin; Sun, Yonghui; Chen, Zhang; Rao, Yu; Advanced Synthesis and Catalysis; vol. 356; nb. 7; (2014); p. 1625 - 1630 View in Reaxys OH

O O N

N O

Rx-ID: 37873376 View in Reaxys 14/80

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Yield

Conditions & References Reaction Steps: 2 1: [Ru2(p-PriC6H4Me)2(μ-Cl)Cl]2; trifluoroacetic acid; trifluoroacetic anhydride; [bis(acetoxy)iodo]benzene / 8 h / 80 °C / |Sealed tube 2: hydrazine hydrate / 8 h / 20 °C / |Sealed tube With [Ru2(p-PriC6H4Me)2(μ-Cl)Cl]2, [bis(acetoxy)iodo]benzene, hydrazine hydrate, trifluoroacetic acid, trifluoroacetic anhydride Yang, Xinglin; Sun, Yonghui; Chen, Zhang; Rao, Yu; Advanced Synthesis and Catalysis; vol. 356; nb. 7; (2014); p. 1625 - 1630 View in Reaxys

OH O OH O

HO OH

Rx-ID: 38409160 View in Reaxys 15/80 Yield

Conditions & References Real time 1H NMR monitoring of enzyme reactions General procedure: Enzyme-mediated hydrolysis of 1, 2, and 3 was monitored by 1H NMR, performing reactions in standard 5mm NMR tubes, containing 500μL of deuterated sodium acetate buffer (20mM), pD 5.87, containing 5mM substrate. Measurement of pD was performed using a glass pH electrode, applying the following relationship pD=pHelectrode+0.41 [21]. Prior to the reactions, the enzyme was diluted by 10-fold in D2O (99.90percent), followed by concentration using an Amicon® Ultra filter (regenerated cellulose 10kDa, Millipore) system, this operation being performed twice. Next, hydrolyses were initiated by the addition of an aliquot of the deuterated enzyme solution and reactions were performed at the optimum temperature of the studied enzyme (30°C or 303K for AbfB and BaAXHd3, 50°C or 323K for AbfA and 60°C or 333K for TxAbf). Control experiments that did not contain enzyme were conducted in parallel, in order to monitor the spontaneous hydrolysis of substrates. After 24h, a small amount of substrate 2 spontaneously hydrolyzed into 2a and 2b — 5percent at 50°C and 15percent at 60°C. Substrates 1 and 3 remained stable over 24h within the considered temperature range. Overall, the stability of the substrates was judged sufficient, since the only sensitive experiment (TxAbf with substrate 2) did not exceed 200min. The enzymemediated hydrolysis of 4 (2mM) was performed in 3mm NMR tubes at 600MHz for improved sensitivity. In typical experiments, upon enzyme addition and mixing, the NMR tube was immediately transferred to the spectrometer, and after temperature stabilization, spectra consisting of an 8-scan accumulation were recorded continuously, thus providing the first spectrum 6 to 10min after enzyme addition.1H NMR scans were accumulated continuously over 1.45min (8 scans with a repetition delay of 6s) during 4 to 15h, depending on the reaction. Each NMR spectrum was acquired using an excitation flip angle of 30° at a radiofrequency field of 29.7kHz, and the residual water signal was pre-saturated during the repetition delay (with a radiofrequency field of 21Hz). The following acquisition parameters were used: relaxation delay (5s) and dummy scans (2). With recombinant B. adolescentis α-L-arabinofuranosidase A (BAF39204.1), water-d2, sodium trideuterioacetate, T= 50 °C , pH= 5.87, Enzymatic reaction, Kinetics Borsenberger, Vinciane; Dornez, Emmie; Desrousseaux, Marie-Laure; Massou, Stéphane; Tenkanen, Maija; Courtin, Christophe M.; Dumon, Claire; O'Donohue, Michael J.; Fauré, Régis; Biochimica et Biophysica Acta General Subjects; vol. 1840; nb. 10; (2014); p. 3106 - 3114 View in Reaxys

O OH

OH O

Rx-ID: 38409161 View in Reaxys 16/80

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Yield

OH O

O O HO

N OH

Rx-ID: 38409174 View in Reaxys 17/80 Yield

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acquired using an excitation flip angle of 30° at a radiofrequency field of 29.7kHz, and the residual water signal was pre-saturated during the repetition delay (with a radiofrequency field of 21Hz). The following acquisition parameters were used: relaxation delay (5s) and dummy scans (2). With recombinant B. adolescentis α-L-arabinofuranosidase B (BAF40305.1), water-d2, sodium trideuterioacetate, Time= 7.28333h, T= 30 °C , pH= 5.87, Enzymatic reaction, Kinetics Borsenberger, Vinciane; Dornez, Emmie; Desrousseaux, Marie-Laure; Massou, Stéphane; Tenkanen, Maija; Courtin, Christophe M.; Dumon, Claire; O'Donohue, Michael J.; Fauré, Régis; Biochimica et Biophysica Acta General Subjects; vol. 1840; nb. 10; (2014); p. 3106 - 3114 View in Reaxys Reaction Steps: 2 1: recombinant B. adolescentis double-substituted xylan α-1,3-L-arabinofuranosidase (AAO67499.1); water-d2; sodium trideuterioacetate / 3.68 h / 30 °C / pH 5.87 / |Enzymatic reaction 2: recombinant B. adolescentis α-L-arabinofuranosidase A (BAF39204.1); water-d2; sodium trideuterioacetate / 50 °C / pH 5.87 / |Enzymatic reaction With recombinant B. adolescentis α-L-arabinofuranosidase A (BAF39204.1), recombinant B. adolescentis doublesubstituted xylan α-1,3-L-arabinofuranosidase (AAO67499.1), water-d2, sodium trideuterioacetate Borsenberger, Vinciane; Dornez, Emmie; Desrousseaux, Marie-Laure; Massou, Stéphane; Tenkanen, Maija; Courtin, Christophe M.; Dumon, Claire; O'Donohue, Michael J.; Fauré, Régis; Biochimica et Biophysica Acta General Subjects; vol. 1840; nb. 10; (2014); p. 3106 - 3114 View in Reaxys Reaction Steps: 2 1: recombinant B. adolescentis double-substituted xylan α-1,3-L-arabinofuranosidase (AAO67499.1); water-d2; sodium trideuterioacetate / 3.68 h / 30 °C / pH 5.87 / |Enzymatic reaction 2: recombinant B. adolescentis α-L-arabinofuranosidase A (BAF39204.1); water-d2; sodium trideuterioacetate / 50 °C / pH 5.87 / |Enzymatic reaction With recombinant B. adolescentis α-L-arabinofuranosidase A (BAF39204.1), recombinant B. adolescentis doublesubstituted xylan α-1,3-L-arabinofuranosidase (AAO67499.1), water-d2, sodium trideuterioacetate Borsenberger, Vinciane; Dornez, Emmie; Desrousseaux, Marie-Laure; Massou, Stéphane; Tenkanen, Maija; Courtin, Christophe M.; Dumon, Claire; O'Donohue, Michael J.; Fauré, Régis; Biochimica et Biophysica Acta General Subjects; vol. 1840; nb. 10; (2014); p. 3106 - 3114 View in Reaxys OH

O N

O– Na +

Rx-ID: 35489656 View in Reaxys 18/80 Yield > 90 %Spectr.

Conditions & References With [((2-pyridyl)bis(3-tert-butylpyrazol-2-yl)methane)Cu2O2](SbF6)2 in methanol, dichloromethane, Time= 1h, T= -78 °C , Inert atmosphere Hoffmann, Alexander; Citek, Cooper; Binder, Stephan; Goos, Arne; Ruebhausen, Michael; Troeppner, Oliver; Ivanovic-Burmazovic, Ivana; Wasinger, Erik C.; Stack, T. Daniel P.; Herres-Pawlis, Sonja; Angewandte Chemie - International Edition; vol. 52; nb. 20; (2013); p. 5398 - 5401; Angew. Chem.; vol. 125; nb. 20; (2013); p. 5508 5512,5 View in Reaxys O

O N O

O N

O O

Rx-ID: 31919277 View in Reaxys 19/80 Yield

Conditions & References With oxygen in water, UV-irradiation, Kinetics Silva, Cláudia Gomes; Faria, Joaquim Luís; ChemSusChem; vol. 3; nb. 5; (2010); p. 609 - 618

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View in Reaxys With 2(3),9(10),16(17),23(24)-(tetraphenoxyphthalocyaninato)lutetium(III) acetate functionalized polystryrene in tetrahydrofuran, Time= 12h, Kinetics, Concentration, Reagent/catalyst Zugle, Ruphino; Nyokong, Tebello; Journal of Molecular Catalysis A: Chemical; vol. 358; (2012); p. 49 - 57 View in Reaxys OH

O N

NH 2

Rx-ID: 31516685 View in Reaxys 20/80 Yield

Conditions & References

95 %

With water, sodium hydroxide, Time= 4h, T= 100 °C Imoto, Mitsutaka; Matsui, Yasunori; Takeda, Motonori; Tamaki, Akihiro; Taniguchi, Hisaji; Mizuno, Kazuhiko; Ikeda, Hiroshi; Journal of Organic Chemistry; vol. 76; nb. 15; (2011); p. 6356 - 6361 View in Reaxys O O

OH F

OH O

O OH F

Rx-ID: 34255969 View in Reaxys 21/80 Yield

Conditions & References

13 %Spectr., 73 %Spectr., 6 %Spectr. O

in chloroform, Time= 1h, T= 0 °C Klenov, M. S.; Churakov, A. M.; Solkan, V. N.; Strelenko, Yu. A.; Tartakovsky, V. A.; Russian Chemical Bulletin; vol. 60; nb. 11; (2011); p. 2263 - 2274,12; Zhurnal Obshchei Khimii; vol. 60; nb. 11; (2012) View in Reaxys

HO O O

Rx-ID: 34255971 View in Reaxys 22/80 Yield

Conditions & References

79 %Spectr., 11 %Spectr., 3 %Spectr. O

With sulfuric acid, Time= 0.0833333h, T= 10 °C Klenov, M. S.; Churakov, A. M.; Solkan, V. N.; Strelenko, Yu. A.; Tartakovsky, V. A.; Russian Chemical Bulletin; vol. 60; nb. 11; (2011); p. 2263 - 2274,12; Zhurnal Obshchei Khimii; vol. 60; nb. 11; (2012) View in Reaxys

O N O

O O

O N

Rx-ID: 34255972 View in Reaxys 23/80 Yield

Conditions & References

87 With sulfuric acid, Time= 0.0833333h, T= 40 °C %Spectr., 6 %Spectr. Klenov, M. S.; Churakov, A. M.; Solkan, V. N.; Strelenko, Yu. A.; Tartakovsky, V. A.; Russian Chemical Bulletin; vol. 60; nb. 11; (2011); p. 2263 - 2274,12; Zhurnal Obshchei Khimii; vol. 60; nb. 11; (2012)

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View in Reaxys O

O S

OH O

Rx-ID: 34255973 View in Reaxys 24/80 Yield

Conditions & References

82 %Spectr., 3 %Spectr., 6 %Spectr.

With epoxysulfonyl fluoride, Time= 0.0833333h, T= 0 °C Klenov, M. S.; Churakov, A. M.; Solkan, V. N.; Strelenko, Yu. A.; Tartakovsky, V. A.; Russian Chemical Bulletin; vol. 60; nb. 11; (2011); p. 2263 - 2274,12; Zhurnal Obshchei Khimii; vol. 60; nb. 11; (2012) View in Reaxys

O N

O O

Rx-ID: 29836095 View in Reaxys 25/80 Yield

Conditions & References With ozone in water, T= 24.84 °C , Ultrasound irradiation, Mechanism Zhao, Lei; Ma, Jun; Zhai, Xuedong; Ultrasonics Sonochemistry; vol. 17; nb. 1; (2010); p. 84 - 91 View in Reaxys OH

O N

Rx-ID: 28629638 View in Reaxys 26/80 Yield

Conditions & References With mercury(II) oxide in ethanol, dimethyl sulfoxide, UV-irradiation, Kinetics, Reagent/catalyst, Concentration Scott Bohle, D.; Spina, Carla J.; Journal of the American Chemical Society; vol. 131; nb. 12; (2009); p. 4397 4404 View in Reaxys Cl

O N

Rx-ID: 308060 View in Reaxys 27/80 Yield 84 %

Conditions & References 2 :p-nitrophenol (69.55 g, 0.5 mole) was dissolved in 10 N HCl (200 ml) in a 1000 ml flask with heating and then cooled down. To the mixture was added 600 ml potassium chlorate (61.25 g, 0.5 mole) solution, gradually with stirring. Stirring was continued for 1 hour after completion of addition and mixture was left overnight at room temperature. After filtration with vacuuming, the filtrate was washed with distilled water and recrystallized with dilute acetic acid solution to yield pale yellow acicular crystal, 2-chloro4-nitro-phenol (80.2 g, m.p. 110-111° C., yield rate 91percent).2-chloro-4-nitro-phenol (64.44 g, 0.4 mole) and 300 ml 4M NaOH solution were refluxed with heating for 6 hours. After cooling down and filtration with vacuuming, the filtrate (crystal) was dissolved in a little warm water (60° C.). The solution was adjusted to pH 2.0 with 10percent HCl and cooled down while stirring. After filtration, the filtrate was recrystallized with water to yield 4-nitro-1,2-benzenediol (52.1 g, yield rate 84percent).To a 1000 ml flask was added 4-nitro-1,2-benzenediol (49.6 g, 0.32 mole), and then 403 ml water and 16 ml 10 N HCl (0.16 mole). While stirring 83.2 g zinc dust (1.28 mole) was added gradually and reaction mixture refluxed with heating for 8 hours. After cooling down and filtration with vacuuming, the filtrate was washed thoroughly with 95percent ethanol and decolor-

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ized by active carbon. Filtration again and evaporation of ethanol was carried out until the solution just started to become turbid. After cooling in freezer and filtration with vacuuming, filtrate was collected as 4-amino-1,2-benzenediol (30.0 g, yield rate 75percent).Dissolve 4-amino-1,2-benzenediol (23.2 g, 0.18 mole) in 95percent ethanol. Under salt ice bath 140 ml 2M NaOH solution and 150 ml dichloromethane solution of 13-methyltetradecanoyl chloride (23.2 g, 0.18 mole) were added simultaneously to the benzenediol solution. Stir at room temperature for 6 hours. Adjust pH to 3.0 with HCl, freeze, and filtrate. Wash the filtrate to neutral with water and recrystallize with 50percent ethanol to yield N-(3,4dihydroxyl-phenyl)-13-methyl-tetradecanamide (55.8 g, m.p. 85-86° C., yield rate 85percent). With sodium hydroxide in water, Time= 6h, Heating / reflux Patent; Yang, Zhenhua; US7109364; (2006); (B2) English View in Reaxys With potassium hydroxide, water van Erp; Chemische Berichte; vol. 64; (1931); p. 2813 View in Reaxys

OH HO

Rx-ID: 9470152 View in Reaxys 28/80 Yield

Conditions & References With dihydrogen peroxide, γ-Irradiation, Product distribution, Further Variations: Reagents Feng, Shao-Hong; Zhang, Shu-Juan; Yu, Han-Qing; Li, Qian-Rong; Chemistry Letters; vol. 32; nb. 8; (2003); p. 718 - 719 View in Reaxys O

OH OH

OH O N

Rx-ID: 619909 View in Reaxys 29/80 Yield 18 %, 48 %

Conditions & References With nitric acid in diethyl ether, Time= 22h, Ambient temperature Cambie, Richard C.; Clark, George R.; Coombe, Sheryl L.; Coulson, Sally A.; Rutledge, Peter S.; Woodgate, Paul D.; Journal of Organometallic Chemistry; vol. 507; nb. 1-2; (1996); p. 1 - 21 View in Reaxys

40 %, 19 %

With nitric acid in diethyl ether, Time= 24h, T= 20 °C Palumbo, Anna; Napolitano, Alessandra; D'Ischia, Marco; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 1; (2002); p. 13 - 16 View in Reaxys

37 % Chromat., 58 % Chromat.

With sodium nitrate, sulfuric acid in diethyl ether, Time= 24h, T= 25 °C , two-phase nitration; gas-phase IP as indicator for nitration; also with 1,3- and 1,4-DHB, Product distribution, Mechanism Thompson, Malcolm J.; Zeegers, Petrus J.; Tetrahedron; vol. 46; nb. 7; (1990); p. 2661 - 2674 View in Reaxys With diethyl ether, nitric acid Vermeulen; Recueil des Travaux Chimiques des Pays-Bas; vol. 25; (1906); p. 17 View in Reaxys With nitric acid in diethyl ether, 0 deg C to rt Ennis; Ghazal; Tetrahedron Letters; vol. 33; nb. 42; (1992); p. 6287 - 6290 View in Reaxys

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With diethyl ether, nitric acid Vermeulen; Recueil des Travaux Chimiques des Pays-Bas; vol. 25; (1906); p. 17 View in Reaxys Weselsky; Benedikat; Monatshefte fuer Chemie; vol. 3; (1882); p. 387 View in Reaxys

Rx-ID: 8671370 View in Reaxys 30/80 Yield

Conditions & References With oxygen, iron(III) cation in water, pH= 2.0, Electrochemical reaction, hydroxylation, Kinetics Oturan; Peiroten; Chartrin; Acher; Environmental Science and Technology; vol. 34; nb. 16; (2000); p. 3474 - 3479 View in Reaxys

O O

Rx-ID: 5280254 View in Reaxys 31/80 Yield

Conditions & References With water, pH= 6.5, sonolysis, Substitution, Kinetics, Further Variations: Reagents Tauber, Armin; Schuchmann, Heinz-Peter; Von Sonntag, Clemens; Chemistry - A European Journal; vol. 5; nb. 7; (1999); p. 2198 - 2202 View in Reaxys HO

OH O O

S O

K+ O–

Rx-ID: 4258429 View in Reaxys 32/80 Yield

Conditions & References With water, T= 37 °C , pH 5.6; hydrolysis with arylsulfatase sulfohydrolase (EC 3.1.6.1); effect concentration, temperature and pH on the hydrolysis rate Hassan, Saad S. M.; Marzouk; Abdel-Fattah; Shouckry; Analytical Chemistry; vol. 67; nb. 11; (1995); p. 1887 1891 View in Reaxys O

O O

OH O

O N

Rx-ID: 4420633 View in Reaxys 33/80 Yield

Conditions & References With water, epoxysulfonyl fluoride, lead dioxide, Yield given. Multistep reaction. Yields of byproduct given Rudenko, A. P.; Russian Journal of Organic Chemistry; vol. 30; nb. 12; (1994); p. 1946 - 1980; Zhurnal Organicheskoi Khimii; vol. 30; nb. 12; (1994); p. 1847 - 1881 View in Reaxys

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HO O

Rx-ID: 5248970 View in Reaxys 34/80 Yield

Conditions & References With nitrophenol oxygenase in phosphate buffer, T= 20 °C , pH= 7.5, Enzymatic reaction, Decomposition, Enzyme kinetics, Further Variations: Reagents Folsom, Brian R.; Stierli, Ruth; Schwarzenbach, Rene P.; Zeyer, Josef; Environmental Science & Technology; vol. 28; nb. 2; (1994); p. 306 - 311 View in Reaxys OH

HO O N

Rx-ID: 5249797 View in Reaxys 35/80 Yield

Conditions & References With nitrophenol oxygenase in phosphate buffer, T= 20 °C , pH= 7.5, Enzymatic reaction, Decomposition, Enzyme kinetics Folsom, Brian R.; Stierli, Ruth; Schwarzenbach, Rene P.; Zeyer, Josef; Environmental Science & Technology; vol. 28; nb. 2; (1994); p. 306 - 311 View in Reaxys

O O

O N

Rx-ID: 159168 View in Reaxys 36/80 Yield

Conditions & References With sulfuric acid Slooff; Recueil des Travaux Chimiques des Pays-Bas; vol. 54; (1935); p. 995,999 View in Reaxys With hydrogen bromide Neiland, O. Ya.; Kraupsha, I. L.; Gudele, I. Ya.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 29; nb. 12; (1993); p. 1428 - 1434; Khimiya Geterotsiklicheskikh Soedinenii; nb. 12; (1993); p. 1653 1661 View in Reaxys

O N

O O

OH –O

O N O

O–

NO2 -, NO3 -, H2O2

Rx-ID: 6730050 View in Reaxys 37/80 Yield

Conditions & References With water, oxygen, T= 30 °C , ultrasound irradiation, Mechanism, Rate constant Kotronarou, A.; Mills, G.; Hoffmann, M. R.; Journal of Physical Chemistry; vol. 95; nb. 9; (1991); p. 3630 - 3638 View in Reaxys

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O O

Rx-ID: 1869509 View in Reaxys 38/80 Yield

Conditions & References With hydrogenchloride, water, water-d2, T= 25 °C , other temp., or acetonitrile, with pH3, kinetic solvent isotope effect, Mechanism, Kinetics Gopalakrishnan, Ganesa; Hogg, John L.; Journal of Organic Chemistry; vol. 49; nb. 17; (1984); p. 3161 - 3166 View in Reaxys OH O N

Rx-ID: 7024164 View in Reaxys 39/80 Yield

Conditions & References Konopik,N.; Wimmer,G.; Monatshefte fuer Chemie; vol. 93; (1962); p. 1404 - 1415 View in Reaxys Marshall; Wilkinson; Pesticide Biochemistry and Physiology; vol. 2; (1972); p. 425,431 View in Reaxys Suarez et al.; Tetrahedron Letters; (1970); p. 575 View in Reaxys Kampouris; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1972); p. 1088 View in Reaxys Merger; Graesslin; Angewandte Chemie; vol. 76; (1964); p. 752 View in Reaxys GUILLAUME; TACQUET; KUPERWASER; Comptes rendus hebdomadaires des séances de l'Académie; vol. 256; (1963); p. 1634 - 1636 View in Reaxys Murakami; Tokunaga; Bulletin of the Chemical Society of Japan; vol. 37; (1964); p. 1562 View in Reaxys Norris; Still; Journal of Labelled Compounds; vol. 9; nb. 4; (1973); p. 661 - 666 View in Reaxys

Rx-ID: 4325236 View in Reaxys 40/80 Yield

Conditions & References With water, Equilibrium constant Havelkova,L.; Bartusek,M.; Collection of Czechoslovak Chemical Communications; vol. 33; (1968); p. 385 - 393 View in Reaxys

O O

N O

O N

Rx-ID: 478932 View in Reaxys 41/80 Yield

Conditions & References With sodium hydroxide Berti; Gazzetta Chimica Italiana; vol. 87; (1957); p. 659,670 View in Reaxys

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OH O

O N

Rx-ID: 22383072 View in Reaxys 42/80 Yield

Conditions & References Reaction Steps: 2 1: acetic acid; aqueous HNO3 2: aqueous NaOH With sodium hydroxide, nitric acid, acetic acid Berti; Gazzetta Chimica Italiana; vol. 87; (1957); p. 659,670 View in Reaxys

O O

N O

Rx-ID: 157491 View in Reaxys 43/80 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide, T= 40 °C Swan; Wright; Journal of the Chemical Society; (1956); p. 1549,1554 View in Reaxys

NaNO2

S OO

OH O

Rx-ID: 5816198 View in Reaxys 44/80 Yield

Conditions & References Rosenblatt et al.; Journal of the American Chemical Society; vol. 75; (1953); p. 3277 View in Reaxys Kapko; Roczniki Chemii; vol. 28; (1954); p. 525; ; (1955); p. 8849 View in Reaxys OH

monopotassium-salt of 4-nitro-2-sulfooxy-phenol

O N

Rx-ID: 7024170 View in Reaxys 45/80 Yield

Conditions & References With sulfuric acid Smith; Journal of the Chemical Society; (1951); p. 2861 View in Reaxys HO

OH O

O N

Rx-ID: 385563 View in Reaxys 46/80 Yield

Conditions & References With potassium hydroxide Barton; Linnell; Senior; Quarterly Journal of Pharmacy and Pharmacology; vol. 18; (1945); p. 41,43 View in Reaxys

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HO O

1 mol aqueous nitric acid

O O

OH O

O N

OH O

Rx-ID: 7433716 View in Reaxys 47/80 Yield

Conditions & References T= 30 - 35 °C , nach dem Behandeln der weiteren Reaktionsprodukte mit aethanol. Kalilauge Barton; Linnell; Senior; Quarterly Journal of Pharmacy and Pharmacology; vol. 18; (1945); p. 41,43 View in Reaxys HO

OH O

Rx-ID: 21997448 View in Reaxys 48/80 Yield

Conditions & References Reaction Steps: 2 1: aqueous nitric acid; acetic acid / 30 - 35 °C 2: ethanolic KOH With potassium hydroxide, nitric acid, acetic acid Barton; Linnell; Senior; Quarterly Journal of Pharmacy and Pharmacology; vol. 18; (1945); p. 41,43 View in Reaxys O HO

OH O N

Rx-ID: 619896 View in Reaxys 49/80 Yield

Conditions & References Ajello; Sigillo; Gazzetta Chimica Italiana; vol. 69; (1939); p. 65,67 View in Reaxys O

O N

Rx-ID: 619897 View in Reaxys 50/80 Yield

Conditions & References With diethyl ether Ajello; Sigillo; Gazzetta Chimica Italiana; vol. 69; (1939); p. 65,67 View in Reaxys OH

ammonium-<5-nitro-2.3-dihydroxy benzoate>

O N

Rx-ID: 7024169 View in Reaxys 51/80 Yield

Conditions & References With CaO, T= 250 °C , p= 20Torr Bolliger; Reuter; Journal and Proceedings of the Royal Society of New South Wales; vol. 72; (1938); p. 329,331

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View in Reaxys

O N

Rx-ID: 22375595 View in Reaxys 52/80 Yield

Conditions & References Reaction Steps: 2 1: water; nitric acid 2: aqueous H2SO4 With sulfuric acid, water, nitric acid Slooff; Recueil des Travaux Chimiques des Pays-Bas; vol. 54; (1935); p. 995,999 View in Reaxys

1,2-bis<2-(-p-toluenesulfonyloxy)ethoxy>amine HO

O N

Rx-ID: 22404396 View in Reaxys 53/80 Yield

Conditions & References Reaction Steps: 3 1: phosphorus (V)-oxide 2: water; nitric acid 3: aqueous H2SO4 With sulfuric acid, water, nitric acid, phosphorus pentoxide Slooff; Recueil des Travaux Chimiques des Pays-Bas; vol. 54; (1935); p. 995,999 View in Reaxys O N

O O

O N

Rx-ID: 329360 View in Reaxys 54/80 Yield

Conditions & References With hydrogenchloride, acetic acid Baker; Kirby; Montgomery; Journal of the Chemical Society; (1932); p. 2876,2878 View in Reaxys

OH O

O N

Rx-ID: 22087241 View in Reaxys 55/80 Yield

Conditions & References Reaction Steps: 2 1: acetic acid; aqueous HNO3 2: concentrated aqueous HCl; acetic acid With hydrogenchloride, nitric acid, acetic acid Baker; Kirby; Montgomery; Journal of the Chemical Society; (1932); p. 2876,2878

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View in Reaxys Cl

KO H

O N

Rx-ID: 7156328 View in Reaxys 56/80 Yield

Conditions & References van Erp; Chemische Berichte; vol. 64; (1931); p. 2813 View in Reaxys

O N

Rx-ID: 5472400 View in Reaxys 57/80 Yield

Conditions & References Mosettig; Burger; Journal of the American Chemical Society; vol. 52; (1930); p. 2988,2992 View in Reaxys

Rx-ID: 7024165 View in Reaxys 58/80 Yield

Conditions & References Cardwell; Robinson; Journal of the Chemical Society; vol. 107; (1915); p. 258 View in Reaxys O

Rx-ID: 22124820 View in Reaxys 59/80 Yield

Conditions & References Reaction Steps: 2 1: aqueous-methanolic KOH-solution 2: aqueous hydrobromic acid With potassium hydroxide, hydrogen bromide Cardwell; Robinson; Journal of the Chemical Society; vol. 107; (1915); p. 258 View in Reaxys HO

O HN O

diluted NaOH-solution

NH 2

Rx-ID: 8265391 View in Reaxys 60/80 Yield

Conditions & References Semper; Lichtenstadt; Justus Liebigs Annalen der Chemie; vol. 400; (1913); p. 328 View in Reaxys

O H

N O

Rx-ID: 5806360 View in Reaxys 61/80

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Yield

Conditions & References Dakin; American Chemical Journal; vol. 42; (1909); p. 495 View in Reaxys OH O

5-nitro-2-oxy-benzaldehyde

Rx-ID: 7024168 View in Reaxys 62/80 Yield

Conditions & References With dihydrogen peroxide Dakin; American Chemical Journal; vol. 42; (1909); p. 495 View in Reaxys O HO

O N

OH O N

Rx-ID: 5806362 View in Reaxys 63/80 Yield

Conditions & References Vermeulen; Recueil des Travaux Chimiques des Pays-Bas; vol. 25; (1906); p. 17 View in Reaxys Weselsky; Benedikt; Monatshefte fuer Chemie; vol. 3; (1882); p. 386 View in Reaxys O

OH O

O N

Rx-ID: 123513 View in Reaxys 64/80 Yield

Conditions & References With water, T= 170 °C , im Einschmelzrohr Mameli; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 14 II; (1905); p. 512; Gazzetta Chimica Italiana; vol. 36 I; (1906); p. 171 View in Reaxys With hydrogenchloride, T= 170 °C , im Einschmelzrohr Mameli; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 14 II; (1905); p. 512; Gazzetta Chimica Italiana; vol. 36 I; (1906); p. 171 View in Reaxys O

OH O

O N

Rx-ID: 5472395 View in Reaxys 65/80 Yield

Conditions & References T= 170 °C , im Rohr Mameli; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 14 II; (1905); p. 512; Gazzetta Chimica Italiana; vol. 36 I; (1906); p. 171 View in Reaxys

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O N

Rx-ID: 5472396 View in Reaxys 66/80 Yield

Conditions & References im Rohr Mameli; Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti; vol. <5> 14 II; (1905); p. 512; Gazzetta Chimica Italiana; vol. 36 I; (1906); p. 171 View in Reaxys

Rx-ID: 5472397 View in Reaxys 67/80 Yield

O N

Rx-ID: 5472399 View in Reaxys 68/80 Yield

4-nitro-pyrocatechol-methylene ether

Rx-ID: 7024167 View in Reaxys 69/80 Yield

OH O

OH OH

OH O

N O

Rx-ID: 281297 View in Reaxys 70/80

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Yield

Conditions & References With peroxymonosulfuric acid Bamberger; Czerkis; Journal fuer Praktische Chemie (Leipzig); vol. <2> 68; (1903); p. 480 View in Reaxys With peroxymonosulfuric acid Bamberger; Czerkis; Journal fuer Praktische Chemie (Leipzig); vol. <2> 68; (1903); p. 480 View in Reaxys O

OH O N

NH 2

Rx-ID: 757525 View in Reaxys 71/80 Yield

OH O N HO

NH 2

Rx-ID: 757528 View in Reaxys 72/80 Yield

Conditions & References With peroxymonosulfuric acid Bamberger; Czerkis; Journal fuer Praktische Chemie (Leipzig); vol. <2> 68; (1903); p. 480 View in Reaxys Reaction Steps: 2 1: sulfomonoperoxoic acid 2: sulfomonoperoxoic acid With peroxymonosulfuric acid Bamberger; Czerkis; Journal fuer Praktische Chemie (Leipzig); vol. <2> 68; (1903); p. 480 View in Reaxys

sulfomonoperoxoic acid HO

NH 2

O O

O N

Rx-ID: 5807236 View in Reaxys 73/80 Yield

Conditions & References Bamberger; Czerkis; Journal fuer Praktische Chemie (Leipzig); vol. <2> 68; (1903); p. 480 View in Reaxys

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OH HO

potassium persulfate

S OO

OH O N

succinic acid peroxide?

Rx-ID: 6731467 View in Reaxys 74/80 Yield

Conditions & References T= 80 - 85 °C Bamberger; Czerkis; Journal fuer Praktische Chemie (Leipzig); vol. <2> 68; (1903); p. 480 View in Reaxys OH

sulfate sulfomonoperoxoic acid

O O O

O N

succinic acid peroxide ?

Rx-ID: 7458095 View in Reaxys 75/80 Yield

Conditions & References T= 80 - 85 °C Bamberger; Czerkis; Journal fuer Praktische Chemie (Leipzig); vol. <2> 68; (1903); p. 480 View in Reaxys OH

NH 2

Rx-ID: 22145509 View in Reaxys 76/80 Yield

Conditions & References Reaction Steps: 2 1: sulfomonoperoxoic acid; diethyl ether 2: sulfomonoperoxoic acid With peroxymonosulfuric acid, diethyl ether Bamberger; Czerkis; Journal fuer Praktische Chemie (Leipzig); vol. <2> 68; (1903); p. 480 View in Reaxys Reaction Steps: 2 1: diethyl ether; sulfomonoperoxoic acid 2: sulfomonoperoxoic acid With peroxymonosulfuric acid, diethyl ether Bamberger; Czerkis; Journal fuer Praktische Chemie (Leipzig); vol. <2> 68; (1903); p. 480 View in Reaxys

NH O

O N

KOH-solution

Rx-ID: 5574871 View in Reaxys 77/80 Yield

Conditions & References v. Chelmicki; Journal fuer Praktische Chemie (Leipzig); vol. <2> 42; (1890); p. 443; Chemische Berichte; vol. 20; (1887); p. 179 View in Reaxys

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KNO2

S OO

Rx-ID: 5806361 View in Reaxys 78/80 Yield

Conditions & References Benedikt; Chemische Berichte; vol. 11; (1878); p. 362 View in Reaxys

O O

OH O O

O N

Rx-ID: 5472398 View in Reaxys 79/80 Yield

Conditions & References Patent; Riedel,J. D.; DE264012; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 193 View in Reaxys OH O

4-nitro-pyrocatechol carbonate

Rx-ID: 7024166 View in Reaxys 80/80 Yield

Conditions & References With water Patent; Riedel,J. D.; DE264012; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 192 View in Reaxys

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