2,2-Dichloropropanoic acid [C3H4Cl2O2]

Page 1

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Citations (37)

References A

B

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1

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With GLUTATHIONE; water; sodium hydroxide in aq. phosphate buffer

T=20°C; pH=7.4; Sealed tube; Kinetics; Hide Experimental Procedure

Mohamed, Heba A.H.; Abdel-Aziz, Mohamed; Abuo-Rahma, Gamal El-Din A.A.; King, S. Bruce

Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 17 p. 6069 - 6077 Title/Abstract Full Text View citing articles Show Details

2.2.2. Kinetic UV–vis decomposition assay

General procedure: Phosphate buffered saline (PBS, 100 mM, pH 7.4, 1 mL) wasadded to a solution of 4 and 5 (60 lmol) in MeOH (1 mL) at rt ina sealed cuvette. UV–vis measurements were taken every 15 minfor 10 h at 667 nm. In other experiments, a solution of NaOH(0.1 M, 1 mL) was used and similar measurements made. Similarmeasurements were performed with the addition of PLE (200 lL,9 U/lmol substrate). Further experiments were performed in thepresence of thiols. A solution of GSH (70.2 lmol) in PBS(100 mM, pH = 7.4, 1 mL) was added to a solution of 4–7(35.1 lmol) in MeOH (1 mL) at rt in a sealed cuvette. UV–vis measurementswere taken every 1 min for 90 min at 665 nm. Similarexperiments were performed using another concentration of GSH(70.2 lmol) in NaOH (0.1 M, 1 mL). A

B

C


2

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C: 92%

With water in methanol; aq. phosphate buffer

T=20°C; pH=7.4; 24 h; Sealed tube; Kinetics; Reagent/catalyst; Hide Experimental Procedure

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Mohamed, Heba A.H.; Abdel-Aziz, Mohamed; Abuo-Rahma, Gamal El-Din A.A.; King, S. Bruce

Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 17 p. 6069 - 6077 Title/Abstract Full Text View citing articles Show Details

2.2.2. Kinetic UV–vis decomposition assay

General procedure: Phosphate buffered saline (PBS, 100 mM, pH 7.4, 1 mL) wasadded to a solution of 4 and 5 (60 lmol) in MeOH (1 mL) at rt ina sealed cuvette. UV–vis measurements were taken every 15 minfor 10 h at 667 nm. In other experiments, a solution of NaOH(0.1 M, 1 mL) was used and similar measurements made. Similarmeasurements were performed with the addition of PLE (200 lL,9 U/lmol substrate). Further experiments were performed in thepresence of thiols. A solution of GSH (70.2 lmol) in PBS(100 mM, pH = 7.4, 1 mL) was added to a solution of 4–7(35.1 lmol) in MeOH (1 mL) at rt in a sealed cuvette. UV–vis measurementswere taken every 1 min for 90 min at 665 nm. Similarexperiments were performed using another concentration of GSH(70.2 lmol) in NaOH (0.1 M, 1 mL). A

B

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3

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A: 10.47% B: 68.23%

With chlorine; carbon; propionic acid anhydride

T=130°C; P=760.051 Torr; 2.5 h;

Xue, Jianwei; Qi, Beibei; Wen, Xiaoguang; Wang, Yingying; Lv, Zhiping; Li, Fuxiang

Asian Journal of Chemistry, 2014 , vol. 26, # 2 p. 481 - 485 Title/Abstract Full Text View citing articles Show Details

4

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Rx-ID: 5263971 Find similar reactions


95%

With hydrogenchloride; picoline hydrochloride; chlorine in chloroform

T=65 - 70°C; Oxidation; 24 h;

Bellesia, Franco; De Buyck, Laurent; Ghelfi, Franco

Synlett, 2000 , # 1 p. 146 - 148 Title/Abstract Full Text View citing articles Show Details

66%

With nitric acid; sodium nitrite in dichloromethane

T=20°C; 192 h;

Bellesia, Franco; De Buyck, Laurent; Ghelfi, Franco; Pagnoni, Ugo M.; Strazzolini, Paolo

Synthetic Communications, 2004 , vol. 34, # 8 p. 1473 - 1481 Title/Abstract Full Text View citing articles Show Details

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5

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With hydrogenchloride; sodium dodecyl-sulfate in water; acetonitrile

T=35°C; pH=1.0 4.0; Kinetics; Further Variations:Temperaturessurfactants;

Seoud, Omar A. E.I.; Ruasse, Marie-Francoise; Possidonio, Shirley

Journal of Physical Organic Chemistry, 2001 , vol. 14, # 8 p. 526 - 532 Title/Abstract Full Text View citing articles Show Details

6

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T=-7°C; 0.25 h;

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Benedetti, Miriam; Forti, Luca; Ghelfi, Franco; Pagnoni, Ugo Maria; Ronzoni, Roberto

Tetrahedron, 1997 , vol. 53, # 41 p. 14031 - 14042 Title/Abstract Full Text View citing articles Show Details

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8

With water in acetonitrile

var. pH; Rate constant;

Hall, C. Dennis; Goulding, Celia W.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995 , # 7 p. 1471 - 1478 Title/Abstract Full Text Show Details

Hide Experimental Procedure

Rx-ID: 6963615 Find similar reactions

Pisarew et al.

J. Gen. Chem. USSR (Engl. Transl.), 1968 , vol. 38, p. 1453,1406 Full Text Show Details

Pechiney

Patent: FR1241836 ; Chem.Abstr., 1961 , # 25758 Full Text Show Details

Tekkosha Co. Ltd

Patent: JP6817164 , 1968 ; Chem.Abstr., 1969 , vol. 70, # 57165g Full Text Show Details

Tanaka; Wien

Journal of Labelled Compounds and Radiopharmaceuticals, 1976 , vol. 12, p. 41,48 Full Text Show Details

BASF AG

Patent: DE1133710 , 1962 ; Chem.Abstr., 1962 , vol. 57, # 16407d Full Text Show Details

Blanchard; Huelder

Journal of Agricultural and Food Chemistry, 1960 , vol. 8, p. 124,125 Full Text Show Details

Riverdale Chemical Company

Patent: US5266553 A1, 1993 ; Title/Abstract Full Text Show Details

(c) other herbicidal and related compounds including a carboxylic acid functionality: 2,2-dichloropropionic acid (dalapon), 7-oxabicyclo[2.2.1]heptane 2,3-dicarboxylic acid (endothall), (2,3,6-trichlorophenyl)acetic acid (fenac), glufosinate, gallic acid, gibberellic acid,

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Bayer Aktiengesellschaft

Patent: US4898608 A1, 1990 ; Title/Abstract Full Text Show Details

The following may be mentioned as examples of compounds of the formula (III): trichloroacetic acid trifluoroacetic acid

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α,α-dichloropropionic acid isobutyric acid α-chloro-isobutyric acid α-bromo-isobutyric acid α-methoxy-isobutyric acid α-phenoxy-isobutyric acid α-(4-chloro-phenoxy)-isobutyric acid α-(2-methyl-4-chloro-phenoxy)-isobytyric acid ...

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Eli Lilly and Company

Patent: US3932428 A1, 1976 ; Title/Abstract Full Text Show Details

and an amount of a second substance which is: alachlor, atrazine, 2-chloro-4-(1-cyano-1-methylethylamino)-6-ethylamino-s-triazine, dalapon, dinoseb, diuron, linuron, oryzalin, propachlor, ...

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Eli Lilly and Company

Patent: US3961937 A1, 1976 ; Title/Abstract Full Text Show Details

and an amount of a second substance which is: alachlor, atrazine, 2-chloro-4-(1-cyano-1-methylethylamino)-6-ethylamino-s-triazine, dalapon, dinoseb, diuron, EPTC, linuron, oryzalin, ...

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Eli Lilly and Company

Patent: US4054573 A1, 1977 ; Title/Abstract Full Text Show Details

and an amount of a second substance which is: ... atrazine, 2-chloro-4-(1-cyano-1-methylethylamino)-6-ethylamino-s-triazine, dalapon, dinoseb, ...

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McCormick; Charles L.

Patent: US4225693 A1, 1980 ; Title/Abstract Full Text Show Details

(b) a group in which X is selected from a single bond, --NH--, --O--, --O--(CH2)2 --NH-and --NH--(CH2)2 --O-- and R is a group obtained by removing a hydroxyl group from a carboxyl group of an acid selected from: trichloroacetic acid 2,2-dichloropropionic acid (2,4-dichlorophenoxy)acetic acid 4-(2,4-dichlorophenoxy)butyric acid 2-(2,4-dichlorophenoxy)propionic acid (2,3,6-trichlorophenyl)acetic acid


2-methyl-4-chlorophenoxyacetic acid (2,4,5-trichlorophenoxy)acetic acid 2,3,6-trichlorobenzoic acid 2,3,5-triiodobenzoic acid ...

9

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Rx-ID: 1927573 Find similar reactions

20.5 h; HeatingIrradiationmolybdenum glass flask, effect of glass composition; Product distribution;

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Martynov, A. V.; Mirskova, A. N.; Vitkovskii, V. Yu.; Voronkov, M. G.

Journal of Organic Chemistry USSR (English Translation), 1985 , vol. 21, # 6 p. 1061 - 1065 Zhurnal Organicheskoi Khimii, 1985 , vol. 21, # 6 p. 1165 - 1169 Title/Abstract Full Text Show Details

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With water; oxygen

17 h; HeatingIrradiation; Further byproducts given;

Martynov, A.V.; Mirskova, A. N.; Vitkovskii, V. Yu.; Voronkov, M. G.

Journal of Organic Chemistry USSR (English Translation), 1985 , vol. 21, p. 631 - 634 Zhurnal Organicheskoi Khimii, 1985 , vol. 21, # 4 p. 698 - 701 Title/Abstract Full Text Show Details

17 h; HeatingIrradiation; Further byproducts given. Title compound not separated from byproducts;

Martynov, A.V.; Mirskova, A. N.; Vitkovskii, V. Yu.; Voronkov, M. G.

Journal of Organic Chemistry USSR (English Translation), 1985 , vol. 21, p. 631 - 634 Zhurnal Organicheskoi Khimii, 1985 , vol. 21, # 4 p. 698 - 701 Title/Abstract Full Text Show Details

A

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17 h; HeatingIrradiation; Further byproducts given. Title compound not separated from byproducts;

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Martynov, A.V.; Mirskova, A. N.; Vitkovskii, V. Yu.; Voronkov, M. G.

Journal of Organic Chemistry USSR (English Translation), 1985 , vol. 21, p. 631 - 634 Zhurnal Organicheskoi Khimii, 1985 , vol. 21, # 4 p. 698 - 701 Title/Abstract Full Text Show Details

A

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D

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17 h; HeatingIrradiation; Further byproducts given. Title compound not separated from byproducts;

Martynov, A.V.; Mirskova, A. N.; Vitkovskii, V. Yu.; Voronkov, M. G.

Journal of Organic Chemistry USSR (English Translation), 1985 , vol. 21, p. 631 - 634 Zhurnal Organicheskoi Khimii, 1985 , vol. 21, # 4 p. 698 - 701 Title/Abstract Full Text Show Details

A

B

C

D

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13

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17 h; HeatingIrradiation; Further byproducts given. Title compound not separated from byproducts;

Martynov, A.V.; Mirskova, A. N.; Vitkovskii, V. Yu.; Voronkov, M. G.

Journal of Organic Chemistry USSR (English Translation), 1985 , vol. 21, p. 631 - 634 Zhurnal Organicheskoi Khimii, 1985 , vol. 21, # 4 p. 698 - 701


Title/Abstract Full Text Show Details

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17 h; HeatingIrradiation; Yield given. Further byproducts given. Title compound not separated from byproducts;

Martynov, A.V.; Mirskova, A. N.; Vitkovskii, V. Yu.; Voronkov, M. G.

Journal of Organic Chemistry USSR (English Translation), 1985 , vol. 21, p. 631 - 634 Zhurnal Organicheskoi Khimii, 1985 , vol. 21, # 4 p. 698 - 701 Title/Abstract Full Text Show Details

A

B

C

D

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15

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17 h; HeatingIrradiation; Further byproducts given. Title compound not separated from byproducts;

Martynov, A.V.; Mirskova, A. N.; Vitkovskii, V. Yu.; Voronkov, M. G.

Journal of Organic Chemistry USSR (English Translation), 1985 , vol. 21, p. 631 - 634 Zhurnal Organicheskoi Khimii, 1985 , vol. 21, # 4 p. 698 - 701 Title/Abstract Full Text Show Details

A

B

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16

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With at-poly(methacrylic acid) in water

T=25°C; ΔG+, ΔH+; further inhibitors; Rate constantThermodynamic dataKinetics;

Jager, Jan; Engberts, Jan B. F. N.

Journal of the American Chemical Society, 1984 , vol. 106, # 11 p. 3331 - 3334 Title/Abstract Full Text View citing articles Show Details

17

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Rx-ID: 3543769 Find similar reactions

With n-butyllithium; lithium diisopropyl amide

1.) THF, hexane, -78 deg C, 5 min., 2.) room temp., 1 h; Yield given. Multistep reaction;

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Coutrot, Philippe; Gadi, Abdelaziz El

Synthesis, 1984 , # 2 p. 115 - 117 Title/Abstract Full Text Show Details

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With hydrogenchloride; water in various solvent(s) T=25°C; var. temps.; ΔG(activ.), ΔH(activ.), ΔS(activ.), ΔCp(activ.); Rate constantThermodynamic dataKinetics;

Holterman, Herman A. J.; Engberts, Jan B. F. N.

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4025 - 4030 Title/Abstract Full Text View citing articles Show Details

With hydrogenchloride; water in various solvent(s) T=25°C; Mechanism;

Holterman, Herman A. J.; Engberts, Jan B. F. N.

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4025 - 4030 Title/Abstract Full Text View citing articles Show Details

With 2-Butoxyethanol; water

T=20 - 48°C; ΔG<*>, ΔH<*>, ΔS<*>, ΔCp<*>; reagents ratio; Rate constantThermodynamic data;

Holterman, Herman A. J.; Engberts, Jan B. F. N.

Journal of the American Chemical Society, 1980 , vol. 102, # 12 p. 4256 - 4257 Title/Abstract Full Text View citing articles Show Details


With water

T=25°C; P=750.06 Torr; hydrolysis, ΔGp(excit.), ΔHp(excit.), ΔSp(excit.), ΔUv(excit.), ΔSv(excit.),solvent and pressure dependence; Rate constantThermodynamic data;

Holterman, Herman A. J.; Engberts, Jan B. F. N.

Journal of the American Chemical Society, 1982 , vol. 104, # 23 p. 6382 - 6384 Title/Abstract Full Text View citing articles Show Details

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A: 9.38 g

With chlorine; phosphorus trichloride

4 h; Heating; Yields of byproduct given;

Holterman, Herman A. J.; Engberts, Jan B. F. N.

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4025 - 4030 Title/Abstract Full Text View citing articles Show Details

With chlorine; phosphorus trichloride

4 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Holterman, Herman A. J.; Engberts, Jan B. F. N.

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4025 - 4030 Title/Abstract Full Text View citing articles Show Details

With chlorine; phosphorus trichloride

4 h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Holterman, Herman A. J.; Engberts, Jan B. F. N.

Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4025 - 4030 Title/Abstract Full Text View citing articles Show Details

A

B

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in acetonitrile

Hide Experimental Procedure

Bayer Aktiengesellschaft

Patent: US4293331 A1, 1981 ; Title/Abstract Full Text Show Details

Variant (b):

Variant (b): 1,340 g of 2-hydroxy-2-(1,1-dichloroethyl)-imidazolidine-4,5-dione were stirred in 3 liters of acetonitrile under reflux (about 81° C.) for about 20 hours.


After cooling the mixture to 20° C., the 12 g of oxamide formed by hydrolysis were filtered off and the filtrate was concentrated to dryness on a rotary evaporator under a water pump vacuum. The residue was kept in a vacuum drying cabinet at 70° C./0.1 mm Hg for several hours, during which a few grams of 2,2-dichloropropionic acid formed by hydrolysis sublimed out. A

B

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21

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Rx-ID: 25283456 Find similar reactions

American Cyanamid Co.

Patent: US4162913 A1, 1979 ; Title/Abstract Full Text Show Details

2:Preparation of 1,2-Dimethyl-3,5-diphenylpyrazolium 2,2-dichloropropionate

EXAMPLE 2 Preparation of 1,2-Dimethyl-3,5-diphenylpyrazolium 2,2-dichloropropionate This example describes the preparation of the new compound of the invention 1,2-dimethyl-3,5-diphenylpyrazolium 2,2-dichloropropionate. 1,2-Dimethyl-3,5-diphenylpyrazolium hydroxide in an H2 O solution was titrated with 2,2-dichloropropionic acid (DALAPON) until pH 7 was obtained. STR11 The H2 O solution was evaporated to an oil and azeotroped several times with toluene/acetone (dry). Hexane/acetone (approximately 5percent) was added to the oil and it solidified to a light yellow solid, filtered, washed with hexane and dried to give 6.3 grams of product, melting point 141° C. to 143° C. Analysis Calculated for N2 O2 Cl2 C20 H20: C, 61.38; H, 5.15; N, 7.16. Found: C, 61.59; H, 5.17; N, 7.38.

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With sodium hydroxide

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Rx-ID: 1127254 Find similar reactions

Khaskin,I.G. et al.

Sov. Prog. Chem. (Engl. Transl.), 1977 , vol. 43, # 12 p. 1304 - 1307,73 - 76 Full Text View citing articles Show Details

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Rx-ID: 1093424 Find similar reactions


With sodium hydrogencarbonate

Rappe,C.; Andersson,K.

Acta Chemica Scandinavica (1947-1973), 1969 , vol. 23, p. 2839 - 2847 Full Text View citing articles Show Details

24

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With water

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Rx-ID: 1053956 Find similar reactions

Shevchenko,V.I. et al.

J. Gen. Chem. USSR (Engl. Transl.), 1967 , vol. 37, p. 1358 - 1363,1284 - 1289 Full Text View citing articles Show Details

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25

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Rx-ID: 6963618 Find similar reactions

im UV-Licht;

Rasuwaew et al.

Zhurnal Obshchei Khimii, 1959 , vol. 29, p. 2978;engl.Ausg.S.2942 Full Text View citing articles Show Details

26

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T=50 - 60°C;

Rasuwaew et al.

Zhurnal Obshchei Khimii, 1959 , vol. 29, p. 2978;engl.Ausg.S.2942 Full Text View citing articles Show Details

27

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With chlorine; phosphorus trichloride

T=180°C;

Dow Chem.Co.

Patent: US2809992 , 1953 ;

With phosphonic acid; chlorine

T=180°C;

Dow Chem.Co.

Patent: US2809992 , 1953 ;

Rx-ID: 198024 Find similar reactions

Full Text Show Details

Full Text Show Details

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With hydrogenchloride

T=140°C;

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Rx-ID: 398306 Find similar reactions

v.Braun; Jostes; Muench

Justus Liebigs Annalen der Chemie, 1927 , vol. 453, p. 134 Full Text View citing articles Show Details

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Rx-ID: 7542095

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T=140°C;

v.Braun; Jostes; Muench

Justus Liebigs Annalen der Chemie, 1927 , vol. 453, p. 134 Full Text View citing articles Show Details

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Rx-ID: 5464481 Find similar reactions

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Otto; Voigt

Journal fuer Praktische Chemie (Leipzig), 1887 , vol. <2>36, p. 92 Full Text View citing articles Show Details

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Zieht schon an der Luft rasch Wasser an und zerfaellt;

Beckurts; Otto

Chemische Berichte, 1885 , vol. 18, p. 226,846 Anm. Full Text View citing articles Show Details

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Rx-ID: 8271179 Find similar reactions

Beckurts; Otto

Chemische Berichte, 1885 , vol. 18, p. 226,846 Anm. Full Text View citing articles Show Details

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Rx-ID: 6963616 Find similar reactions

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Beckurts; Otto

Chemische Berichte, 1876 , vol. 9, p. 1593 Chemische Berichte, 1877 , vol. 10, p. 2040 Full Text View citing articles Show Details

34

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T=120°C;

Rx-ID: 6963617 Find similar reactions

Beckurts; Otto

Chemische Berichte, 1876 , vol. 9, p. 1593 Chemische Berichte, 1877 , vol. 10, p. 2040 Full Text View citing articles Show Details

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