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Citations (38)
References
1
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Rx-ID: 80598 Find similar reactions
99%
With ammonium cerium(IV) nitrate; lithium bromide in acetonitrile
T=20°C; 2 h;
Roy, Subhas Chandra; Guin, Chandrani; Rana, Kalyan Kumar; Maiti, Gourhari
Tetrahedron Letters, 2001 , vol. 42, # 39 p. 6941 - 6942 Title/Abstract Full Text View citing articles Show Details
98%
With N-Bromosuccinimide; (Z)-N-[3,5bis(trifluoromethyl)phenyl]-4-(dimethyliminio)pyridine-1(4H)carbimidothioate in dichloromethane
T=25°C; 36 h; Darkness; regioselective reaction;
Xiong, Xiaodong; Tan, Fei; Yeung, Ying-Yeung
Organic Letters, 2017 , vol. 19, # 16 p. 4243 - 4246 Title/Abstract Full Text View citing articles Show Details
94%
With N-Bromosuccinimide in acetonitrile
T=0 - 20°C; Inert atmosphere;
Zysman-Colman, Eli; Arias, Karla; Siegel, Jay S.
Canadian Journal of Chemistry, 2009 , vol. 87, # 2 p. 440 - 447 Title/Abstract Full Text View citing articles Show Details
93%
With N-Bromosuccinimide
Steinke, Nelli; Frey, Wolfgang; Baro, Angelika; Laschat, Sabine; Drees, Christina; Nimtz, Manfred; Haegele, Constanze; Giesselmann, Frank
Chemistry - A European Journal, 2006 , vol. 12, # 4 p. 1026 - 1035 Title/Abstract Full Text View citing articles Show Details
93%
With N-Bromosuccinimide in various solvent(s) T=27°C; 0.416667 h;
Yadav; Reddy; Basak; Narsaiah
Advanced Synthesis and Catalysis, 2004 , vol. 346, # 1 p. 77 - 82 Title/Abstract Full Text View citing articles Show Details
93%
With hydrogen bromide; 2-methylpyridinium nitrate in water
T=60°C; 5 h; Green chemistry; Temperature;
Wang, Jian; Chen, Shu-Bin; Wang, Shu-Guang; Li, Jing-Hua
Australian Journal of Chemistry, 2015 , vol. 68, # 3 p. 513 - 517 Title/Abstract Full Text View citing articles Show Details
93%
With ammonium cerium (IV) nitrate; lithium bromide in acetonitrile
T=20°C; 6 h;
Rao, Maddali L. N.; Murty, Venneti N.
European Journal of Organic Chemistry, 2016 , vol. 2016, # 12 p. 2177 - 2186 Title/Abstract Full Text View citing articles Show Details
92%
With gold(III) chloride; N-Bromosuccinimide in dichloromethane
T=20°C; 4 h; Inert atmosphere;
Mo, Fanyang; Yan, Jerry Mingtao; Qiu, Di; Li, Fei; Zhang, Yan; Wang, Jianbo
Angewandte Chemie - International Edition, 2010 , vol. 49, # 11 p. 2028 - 2032 Title/Abstract Full Text View citing articles Show Details
91%
With hydrogen bromide; oxygen; sodium nitrite in acetonitrile
T=25°C; 1 h;
Zhang, Guofu; Liu, Renhua; Xu, Qing; Ma, Lixin; Liang, Xinmiao
Advanced Synthesis and Catalysis, 2006 , vol. 348, # 7-8 p. 862 - 866 Title/Abstract Full Text View citing articles Show Details
90%
With N-Bromosuccinimide in chloroform
Bromination; 3.5 h; Heating;
Magnus; Bailey; Porter
Tetrahedron, 1999 , vol. 55, # 49 p. 13927 - 13936 Title/Abstract Full Text View citing articles Show Details
90%
With N-Bromosuccinimide in chloroform
3 h; Reflux; Hide Experimental Procedure
BIOENERGENIX; McCall, John M.; Romero, Donna L.
Patent: US2014/128392 A1, 2014 ; Location in patent: Paragraph 0309; 0310 ; Title/Abstract Full Text Show Details
20.1:5-Bromobenzo[d][1,3]dioxole
A solution of benzo[d][1,3]dioxole (6.1 g, 50.00 mmol, 1.00 equiv) and N-bromo-succinamide (NBS) (9.3 g, 52.5 mmol, 1.05 equiv) in CHCl3 (25 mL) in a 100-mL round-bottom flask and allowed to react, with stirring, for 3 hr while the temperature was maintained at reflux. The resulting mixture was concentrated under vacuum and purified via silica gel column (ethyl acetate:petroleum ether (1:20)) giving 9.5 g (90percent) of 5-bromobenzo[d][1,3]dioxole as yellow oil. 87%
With copper(II) choride dihydrate; ethanol; carbon dioxide; oxygen; lithium bromide
T=20 100°C; P=67506.8 Torr; 12 h; Autoclave; regioselective reaction;
Liu, An-Hua; He, Liang-Nian; Hua, Fang; Yang, Zhen-Zhen; Huang, Cheng-Bin; Yu, Bing; Li, Bin
Advanced Synthesis and Catalysis, 2011 , vol. 353, # 17 p. 3187 - 3195 Title/Abstract Full Text View citing articles Show Details
85%
With bromine in acetic acid
1 h;
Keck,G.E.; Webb,R.R.
Journal of the American Chemical Society, 1981 , vol. 103, p. 3173 Full Text View citing articles Show Details
85%
With N-Bromosuccinimide; silica gel; toluene-4-sulfonic acid in dichloromethane
T=20°C; 3 h;
Costa, Eduarda C.; Cassamale, Tatiana B.; Carvalho, Diego B.; Bosquiroli, Lauriane S. S.; Ojeda, Mariáh; Ximenes, Thalita V.; Matos, Maria F. C.; Kadri, Mônica C. T.; Baroni, Adriano C. M.; Arruda, Carla C. P.
Molecules, 2016 , vol. 21, # 6 art. no. 802 Title/Abstract Full Text View citing articles Show Details
79%
With N-Bromosuccinimide; silica gel; toluene-4-sulfonic acid in dichloromethane
T=0 - 20°C; 3 h; Inert atmosphere; Hide Experimental Procedure
Cassamale, Tatiana B.; Costa, Eduarda C.; Carvalho, Diego B.; Cassemiro, Nadla S.; Tomazela, Carolina C.; Marques, Maria C. S.; Ojeda, Mariáh; Matos, Maria F. C.; Albuquerque, Sérgio; Arruda, Carla C. P.; Baroni, Adriano C. M. Journal of the Brazilian Chemical Society, 2016 , vol. 27, # 7 p. 1217 - 1228 Title/Abstract Full Text View citing articles Show Details
General procedure for the preparation of aryl bromides (21b-c)
General procedure: To a solution of compounds 20b and 20c (75 mmol) in dichloromethane (210 mL) containing TsOH (10mmol), silica gel G 60 230-400 mesh (37 g) in nitrogen atmosphere at 0 °C, was added NBS (75 mmol) slowly.The reaction was stirred at room temperature by 3 hours.The work up was performed with 300 mL of saturated NaHCO3 solution and the product was extracted with ethylacetate (3 × 150 mL). The organic phase was dried over MgSO4 and the solvent removed under reduced pressure.The products were purified by distillation at low pressure (3 mmHg).
72%
With dihydrogen peroxide; ammonium bromide; acetic acid
T=20°C; 22 h;
Krishna Mohan; Narender; Srinivasu; Kulkarni; Raghavan
Synthetic Communications, 2004 , vol. 34, # 12 p. 2143 - 2152 Title/Abstract Full Text View citing articles Show Details
71%
With [bis(acetoxy)iodo]benzene; lithium bromide in tetrahydrofuran
T=20°C; 0.5 h;
Braddock, D. Christopher; Cansell, Gemma; Hermitage, Stephen A.
Synlett, 2004 , # 3 p. 461 - 464 Title/Abstract Full Text View citing articles Show Details
70.8%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione in acetic acid
T=60 - 90°C; 1 h;
UBE INDUSTRIES, LTD.
Patent: WO2007/20964 A1, 2007 ; Location in patent: Page/Page column 9 ; Title/Abstract Full Text Show Details
63%
With gold(III) chloride; N-Bromosuccinimide in 1,2-dichloroethane
T=20°C; 2 h;
Hearne, Zoë; Li, Chao-Jun
Chemical Communications, 2017 , vol. 53, # 45 p. 6136 - 6139 Title/Abstract Full Text View citing articles Show Details
With air; bromine; acetic acid
Jones; Robinson
Journal of the Chemical Society, 1917 , vol. 111, p. 913 Full Text View citing articles Show Details
With N-Bromosuccinimide; chloroform
Gensler; Stouffer
Journal of Organic Chemistry, 1958 , vol. 23, p. 908 Full Text View citing articles Show Details
With N-Bromosuccinimide in PE; chloroform; water
Merck Patent Gesellschaft mit beschrankter Haftung
Patent: US5635107 A1, 1997 ;
Hide Experimental Procedure
Title/Abstract Full Text Show Details
1.a:Example 1 a) 0.487 mol of 1,2-methylenedioxybenzene and 0.512 mol of NBS are refluxed together for three hours in 250 ml of CHCl3. The reaction solution is left to stand overnight and is then evaporated. The residue is taken up in PE/H2 O, washed with H2 O, dried, filtered through silica gel and evaporated on a rotary evaporator. The residue is distilled, giving 1,2-methylenedioxy-4-bromobenzene. Stage #1: With cerium(IV)diammonium nitrate; lithium bromide in acetonitrile
T=25°C; 0.5 h; Stage #2: Methylenedioxybenzene in acetonitrile
T=25°C; 4 h; Hide Experimental Procedure
REDDY US THERAPEUTICS, INC.; KALLEDA, Srinivas; PADAKANTI, Srinivas; KUMAR SWAMY, Nalivela; YELESWARAPU, Koteswar, Rao; ALEXANDER, Christopher, W.; KHANNA, Ish, Kumar; IQBAL, Javed; PILLARISETTI, Sivaram; PAL, Manojit; BARANGE, Deepak
Patent: WO2006/34473 A2, 2006 ; Location in patent: Page/Page column 236-237 ; Title/Abstract Full Text Show Details
95.i: bromide (1.5 g, 18.0 mmol) in acetonitrile (20 mL) was stirred for 30 minutes at 25°C EPO <DP n="238"/>under nitrogen atmosphere. A solution of benzo[l,3]dioxol (2 g, 16 mmol) in acetonitrile (20 mL) was added slowly to it and the mixture was stirred for 4 hours aΛ 250C. The mixture was then diluted with water (50 mL) and extracted with ethyl acetate (3 x 50 mL). The organic layers were collected, combined, washed with watei (50 mL), dried over anhydrous sodium sulphate, and concentrated under vacuum to give the desired product.1H NMR (200 MHz, DMSO-J6): δ 6.95 (s, IH), 6.84 (d, J = 5.3 Hz, IH), 6.71 (d, J = 5.3 Hz, IH), 5.96 (s, 2H). IR (KBr, cm"1): 1594, 1474. MS: m/z (CI) 203 (M+2, 50percent).Reference: Roy, S. C; Guin, C; Rana, K. K.; Maiti, G. Tetrahedron Lett. 2001, 42, 6941 - 6942.
100 % Spectr.
With hydrogen bromide; isopentyl nitrite in dichloromethane
T=20°C; 4 h;
Gavara, Laurent; Boisse, Thomas; Rigo, Benoit; Henichart, Jean-Pierre
Tetrahedron, 2008 , vol. 64, # 22 p. 4999 - 5004 Title/Abstract Full Text View citing articles Show Details
80 %Chromat.
With carbon dioxide; oxygen; lithium bromide; copper(ll) bromide in water
T=100°C; 10 h; AutoclaveGreen chemistry; regioselective reaction; Hide Experimental Procedure
Liu, An-Hua; Ma, Ran; Zhang, Meng; He, Liang-Nian
Catalysis Today, 2012 , vol. 194, # 1 p. 38 - 43 Title/Abstract Full Text View citing articles Show Details
oxybromination of aromatic ethers
General procedure: A mixture of substrate (1 mmol), CuBr2 (22.4 mg, 10 molpercent), LiBr (130.3 mg, 1.5 equiv.), and 0.05 mL of water was placed in a 50 mL stainless steel autoclave equipped with an inner glass tube in room temperature. CO2 (4 MPa) and O2 (1 MPa) were subsequently introduced into the autoclave and the system was heated under the predetermined reaction temperature for 15 min to reach the equilibration. Then the
final pressure was adjusted to the desired pressure by introducing the appropriate amount of CO2. The mixture was stirred continuously for the desired reaction time. After cooling, products were diluted with acetone and analyzed by gas chromatograph (Shimadzu GC-2014) equipped with a capillary column (RTX-17 30 m × 25 μm and RTX-wax 30 m × 25 μm) using a flame ionization detector by comparing the retention times of authentic samples. The residue was purified by column chromatography on silica gel (200–300 mesh, eluting with petroleum ether/ethyl acetate from petroleum ether to 50:1) to afford the desired product. The isolated products were further identified with NMR spectra (Bruker 400 MHz) and GC–MS or GCD, which are consistent with those reported in the literature.
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Rx-ID: 38014806 Find similar reactions
Multi-step reaction with 2 steps 1: caesium carbonate / dimethyl sulfoxide / 2 h / 80 °C / |Inert atmosphere 2: N-Bromosuccinimide / chloroform / 2 h / |Reflux View Scheme
Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge
Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: sodium hydride; N,N,N,N,N,N-hexamethylphosphoric triamide / 0.33 h / |Inert atmosphere 2: N-Bromosuccinimide / chloroform / 2 h / |Reflux View Scheme
CHIRON AS; Johansen, Jon Eigill; Liu, Huiling; Karlsen, Morten
Patent: US9435816 B2, 2016 ; Title/Abstract Full Text Show Details
3
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Rx-ID: 38014815 Find similar reactions
89%
With N-Bromosuccinimide in chloroform
2 h; Reflux;
Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge
Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details
89%
With N-Bromosuccinimide in chloroform
2 h; Reflux; Hide Experimental Procedure
CHIRON AS; Johansen, Jon Eigill; Liu, Huiling; Karlsen, Morten
Patent: US9435816 B2, 2016 ; Location in patent: Page/Page column 16 ; Title/Abstract Full Text Show Details
3.2:3.2 The Synthesis of 3,4-Methylenedioxy-[’3C5] -1- bromobenzene
3,4-methylenedioxy-[’3C5] -benzene (1.5 g, 11.7 mmol)was dissolved in chloroform (20 mE). N-bromosuccinimide (2.16 g, 12.1 mmol) was added in small portions with intensive magnetics stirring. The reaction mixture was refluxed for 2 hours. The obtained solids were removed by filtration and washed with two small portions of cold chlo55 roform. The combined organic fractions were evaporated,and ether (150 mE) was added before washing with water (100 mE). The organic phase was purified by dry flash on a plug of silica in a l3uchner funnel using ether as the mobile phase. The yield of 3,4-methylenedioxy-[’3C5]-1-bro-mobenzene was 2.17 g corresponding to 89percent based on methylenedioxy- [1 3C6] -benzene. With N-Bromosuccinimide in chloroform
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CHIRON A/S; Johansen, Jon Eigill; Liu, Huiling; Karlsen, Morten
Patent: US2014/227792 A1, 2014 ; Location in patent: Page/Page column ;
Title/Abstract Full Text Show Details
3.2:3.2
3.2 The Synthesis of 3,4-Methylenedioxy-[13C6]-1-bromobenzene
3,4-methylenedioxy-[13C6]-benzene (1.5 g, 11.7 mmol) was dissolved in chloroform (20 mL). N-bromosuccinimide (2.16 g, 12.1 mmol) was added in small portions with intensive magnetics stirring. The The The The The
reaction mixture was refluxed for 2 hours. obtained solids were removed by filtration and washed with two small portions of cold chloroform. combined organic fractions were evaporated, and ether (150 mL) was added before washing with water (100 mL). organic phase was purified by dry flash on a plug of silica in a Buchner funnel using ether as the mobile phase. yield of 3,4-methylenedioxy-[13C6]-1-bromobenzene was 2.17 g corresponding to 89percent based on methylenedioxy-[13C6]-benzene.
4
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Rx-ID: 38014771 Find similar reactions
Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge
Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details
5
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Rx-ID: 38014801 Find similar reactions
Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge
Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details
A
B
6
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With N-bromosuccinmide; chloro-trimethyl-silane in acetonitrile
T=20°C; 1 h; Overall yield = 181 mg; regioselective reaction; Hide Experimental Procedure
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Maibunkaew, Tapanee; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Bunrit, Anon; Ruchirawat, Somsak
Synlett, 2014 , vol. 25, # 12 art. no. ST-2014-U0267-L, p. 1769 - 1775 Title/Abstract Full Text View citing articles Show Details
General procedure for the electrophilic aromatic halogenation. 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2,4-dichloro-1-methoxybenzene (2a-diCl)
General procedure: To a solution of 4-bromoanisole (200.8 mg, 1.09 mmol, 1.0 equiv) in acetonitrile (2 mL) was added N-chlorosuccinimide(NCS) (158.3 mg, 1.19 mmol, 1.1 equiv) at rt to give a slightly cloudy mixture. Chlorotrimethylsilane (TMSCl) (14 μL, 0.11 mmol, 0.1 equiv) was then added drop-wise to the reaction mixture. Within a few minutes, the reaction mixture became clear pale yellow solution. The mixture continued to stir at rt for 1 h and was diluted with hexane. The biphasic mixture was concentrated on a rotary evaporator to a crude white solid-oil mixture. This mixture was taken up in hexane and filtered through a short plug of SiO2 and eluted with 5-10percent EtOAc-hexane solution. The clear filtrate was concentrated to obtain a mixture of 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2,4-dichloro-1-methoxybenzene (2a-diCl) 237.0 mg (88percent of 2a-Cl and 11percent of 2a-diCl,based on NMR ratio 2a-Cl: 2a-diCl = 7.1: 1.0; as a pale yellow solid).
7
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8
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Rx-ID: 31770512 Find similar reactions
94%
With [Cp*Ru(CH3CN)3]OTf; lithium bromide
T=100°C; 12 h; Inert atmosphere;
Imazaki, Yusuke; Shirakawa, Eiji; Ueno, Ryota; Hayashi, Tamio
Journal of the American Chemical Society, 2012 , vol. 134, # 36 p. 14760 - 14763 Title/Abstract Full Text View citing articles Show Details
83%
With potassium fluoride; tris(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; potassium bromide in 1,4-dioxane
T=130°C; 16 h; Inert atmosphere;
Pan, Jun; Wang, Xinyan; Zhang, Yong; Buchwald, Stephen L.
Organic Letters, 2011 , vol. 13, # 18 p. 4974 - 4976 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 5428746 Find similar reactions
Weinstein,B.; Craig,A.R.
Journal of Organic Chemistry, 1976 , vol. 41, # 5 p. 875 - 878 Full Text View citing articles Show Details
Feugeas
Bulletin de la Societe Chimique de France, 1964 , p. 1892 Full Text Show Details
Normant; Feugeas
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1964 , vol. 258, p. 2846 Full Text Show Details
Prugh; McCarthy
Tetrahedron Letters, 1966 , p. 1351 Full Text View citing articles Show Details
Hide Experimental Procedure
Syntex U.S.A. Inc.
Patent: US5716954 A1, 1998 ; Title/Abstract Full Text Show Details
By following the procedures of Example 20A and substituting for 1-bromo-3-chlorobenzene with the following: 1-bromo-3-thiomethylbenzene; 1-bromo-3-methylbenzene; 1-bromo-3-trifluoromethylbenzene; 1-bromo-3,4-methylenedioxybenzene; 1-chloro-3-thiomethylbenzene; 1-chloro-3-methylbenzene; 1-chloro-3-trifluoromethylbenzene; 1-chloro-3,4-methylenedioxybenzene; 1-chloro-3-methoxybenzene; ...
9
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With tert-butyldimethylsilyl chloride in tetrachloromethane
T=70°C; 4.5 h;
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Rx-ID: 4898301 Find similar reactions
Gesson, Jean-Pierre; Mondon, Martine; Pokrovska, Natacha
Synlett, 1997 , # 12 p. 1395 - 1396 Title/Abstract Full Text View citing articles Show Details
A
B
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10
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Rx-ID: 4898302 Find similar reactions
With chloro-trimethyl-silane in toluene
Ambient temperature;
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Gesson, Jean-Pierre; Mondon, Martine; Pokrovska, Natacha
Synlett, 1997 , # 12 p. 1395 - 1396 Title/Abstract Full Text View citing articles Show Details
11
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Rx-ID: 16962699 Find similar reactions
Multi-step reaction with 2 steps 1: 60 percent / NaIO4
2: 70 percent / TBDMSCl / CCl4 / 4.5 h / 70 °C View Scheme
Gesson, Jean-Pierre; Mondon, Martine; Pokrovska, Natacha
Synlett, 1997 , # 12 p. 1395 - 1396 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: 60 percent / NaIO4
2: TMSCl / toluene / Ambient temperature View Scheme
Gesson, Jean-Pierre; Mondon, Martine; Pokrovska, Natacha
Synlett, 1997 , # 12 p. 1395 - 1396 Title/Abstract Full Text View citing articles Show Details
12
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Rx-ID: 77142 Find similar reactions
Gensler; Stouffer
Journal of Organic Chemistry, 1958 , vol. 23, p. 908 Full Text View citing articles Show Details
A
13
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B
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Synthesize Find similar With sulfuric acid; sodium nitrite
T=0°C; Diazotization.Zersetzen des Diazoniumsalzes mit einer waessr. Loesung von Kaliumbromid, Natriumhypophosphit und Kupfersulfat;
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Rx-ID: 5428747 Find similar reactions
Mameli; Boi
Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1906 , vol. <5> 15 II, p. 104 Gazzetta Chimica Italiana, 1906 , vol. 36 II, p. 380 Full Text View citing articles Show Details