Product Name

  • Name

    4-Chloro-1,2-diaminobenzene

  • EINECS 202-456-8
  • CAS No. 95-83-0
  • Article Data93
  • CAS DataBase
  • Density 1.345 g/cm3
  • Solubility 16 g/L (20 °C) in water
  • Melting Point 70-75 °C
  • Formula C6H7ClN2
  • Boiling Point 300.2 °C at 760 mmHg
  • Molecular Weight 142.588
  • Flash Point 135.4 °C
  • Transport Information UN 2811
  • Appearance brown crystalline solid or powder
  • Safety 26-36/37
  • Risk Codes 36/37/38-40
  • Molecular Structure Molecular Structure of 95-83-0 (4-Chloro-1,2-diaminobenzene)
  • Hazard Symbols HarmfulXn
  • Synonyms o-Phenylenediamine,4-chloro- (6CI,7CI,8CI);1,2-Diamino-4-chlorobenzene;2-Amino-4-chloroaniline;2-Amino-4-chlorobenzenamine;2-Amino-5-chloroaniline;3,4-Diamino-1-chlorobenzene;3,4-Diaminochlorobenzene;3-Chloro-1,6-phenylenediamine;4-Chloro-1,2-benzenediamine;
  • PSA 52.04000
  • LogP 2.66680

Synthetic route

4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
With samarium; 1,1’-di-n-octyl-4,4’-bipyridinium dibromide In methanol at 20℃; for 5.5h;99%
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; for 0.133333h; Microwave irradiation; chemoselective reaction;98%
With palladium/alumina; hydrogen In ethanol at 125℃; for 8h; Flow reactor;96%
3,4-dinitro-chlorobenzene
610-40-2

3,4-dinitro-chlorobenzene

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
With sodium tetrahydroborate; C16H18Cl2N4O2Pd In water at 27℃; for 0.25h;99%
With hydrogenchloride; tin
With sodium tetrahydroborate In water at 20℃; for 40h;
5-chloro-2-nitroaniline
1635-61-6

5-chloro-2-nitroaniline

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
With hydrogen at 130℃; under 750.075 Torr; for 6h; chemoselective reaction;99%
With iron(III)-acetylacetonate; hydrazine hydrate In methanol under 25502.6 Torr; chemoselective reaction;98%
With 5%-palladium/activated carbon; hydrazine hydrate In methanol at 20℃; for 0.0833333h;93%
5-chlorobenzofurazan-1-oxide
17348-69-5

5-chlorobenzofurazan-1-oxide

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
With Saccharomyces cerevisiae BY In methanol at 20℃; for 6.5h; pH=7.0; aq. buffer; Enzymatic reaction;90%
With ammonium sulfate; magnesium In methanol Ambient temperature;85%
5-chloro-2,1,3-benzothiadiazole
2207-32-1

5-chloro-2,1,3-benzothiadiazole

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
With methanol; samarium diiodide In tetrahydrofuran at 20℃; for 0.25h;82%
(5-chloro-2-nitro-phenyl)-(3,5-di-tert-butyl-2-methoxy-phenyl)-diazene

(5-chloro-2-nitro-phenyl)-(3,5-di-tert-butyl-2-methoxy-phenyl)-diazene

A

3,5-di-tert-butyl-2-methoxyaniline
893397-17-6

3,5-di-tert-butyl-2-methoxyaniline

B

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

C

2-[3,5-bis(1,1-dimethylethyl)-2-methoxyphenyl]-5-chloro-2H-benzotriazole
271788-60-4

2-[3,5-bis(1,1-dimethylethyl)-2-methoxyphenyl]-5-chloro-2H-benzotriazole

D

2-[3,5-bis(1,1-dimethylethyl)-2-methoxyphenyl]-5-chloro-1-oxido-2H-benzotriazole

2-[3,5-bis(1,1-dimethylethyl)-2-methoxyphenyl]-5-chloro-1-oxido-2H-benzotriazole

Conditions
ConditionsYield
With lithium perchlorate In methanol; dichloromethane at 20℃; Cyclization; Electrolysis;A n/a
B n/a
C 1%
D 79%
4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

A

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

B

C12H12Cl2N4

C12H12Cl2N4

Conditions
ConditionsYield
With samarium; iodine; ammonium chloride In tetrahydrofuran; water at 20℃; for 6h; Reduction;A 74%
B 14%
(5-chloro-2-nitro-phenyl)-(3,5-di-tert-butyl-2-methoxy-phenyl)-diazene

(5-chloro-2-nitro-phenyl)-(3,5-di-tert-butyl-2-methoxy-phenyl)-diazene

A

3,5-di-tert-butyl-2-methoxyaniline
893397-17-6

3,5-di-tert-butyl-2-methoxyaniline

B

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

C

2-[3,5-bis(1,1-dimethylethyl)-2-methoxyphenyl]-5-chloro-2H-benzotriazole
271788-60-4

2-[3,5-bis(1,1-dimethylethyl)-2-methoxyphenyl]-5-chloro-2H-benzotriazole

Conditions
ConditionsYield
With sodium hydroxide; lithium perchlorate In tetrahydrofuran; water at 20℃; Cyclization; Electrolysis;A n/a
B n/a
C 63%
(4-chloro-2-nitro-phenyl)-(3,5-di-tert-butyl-2-methoxy-phenyl)-diazene

(4-chloro-2-nitro-phenyl)-(3,5-di-tert-butyl-2-methoxy-phenyl)-diazene

A

3,5-di-tert-butyl-2-methoxyaniline
893397-17-6

3,5-di-tert-butyl-2-methoxyaniline

B

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

C

2-[3,5-bis(1,1-dimethylethyl)-2-methoxyphenyl]-5-chloro-2H-benzotriazole
271788-60-4

2-[3,5-bis(1,1-dimethylethyl)-2-methoxyphenyl]-5-chloro-2H-benzotriazole

D

2-[3,5-bis(1,1-dimethylethyl)-2-methoxyphenyl]-6-chloro-1-oxido-2H-benzotriazole

2-[3,5-bis(1,1-dimethylethyl)-2-methoxyphenyl]-6-chloro-1-oxido-2H-benzotriazole

Conditions
ConditionsYield
With lithium perchlorate In methanol; dichloromethane at 20℃; Cyclization; Electrolysis;A n/a
B n/a
C 12%
D 60%
With sodium hydroxide; lithium perchlorate In tetrahydrofuran; water at 20℃; Cyclization; Electrolysis;A n/a
B n/a
C 45%
D 28%
2-nitro-4-chloro-2'-hydroxy-3',5'-di-tert-butylazobenzene
52184-29-9

2-nitro-4-chloro-2'-hydroxy-3',5'-di-tert-butylazobenzene

A

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

B

2-amino-4,6-di-tertbutylphenol
1643-39-6

2-amino-4,6-di-tertbutylphenol

C

2-(5'-chloro-2'H-benzotriazol-2'-yl)-4,6-di-tert-butylphenol
3864-99-1

2-(5'-chloro-2'H-benzotriazol-2'-yl)-4,6-di-tert-butylphenol

Conditions
ConditionsYield
With 2-bromo-2-nitropropane; zinc In methanol; dichloromethane for 4h; Ambient temperature;A n/a
B n/a
C 88 % Chromat.
2,4-di-tert-butyl-6-(5-chloro-2-nitro-phenylazo)-phenol

2,4-di-tert-butyl-6-(5-chloro-2-nitro-phenylazo)-phenol

A

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

B

2-amino-4,6-di-tertbutylphenol
1643-39-6

2-amino-4,6-di-tertbutylphenol

C

2-(5'-chloro-2'H-benzotriazol-2'-yl)-4,6-di-tert-butylphenol
3864-99-1

2-(5'-chloro-2'H-benzotriazol-2'-yl)-4,6-di-tert-butylphenol

Conditions
ConditionsYield
With 2-bromo-2-nitropropane; zinc In methanol; dichloromethane for 3.5h; Ambient temperature;A n/a
B n/a
C 79 % Chromat.
ethanol
64-17-5

ethanol

acetic acid
64-19-7

acetic acid

2-(4-chloro-2-nitro-phenylhydrazono)-3-oxo-butyric acid anilide
117616-89-4

2-(4-chloro-2-nitro-phenylhydrazono)-3-oxo-butyric acid anilide

zinc dust

zinc dust

A

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

B

3.6-dimethyl-2.5-dihydro-pyrazine-dicarboxylic acid-(2.5)-dianilide

3.6-dimethyl-2.5-dihydro-pyrazine-dicarboxylic acid-(2.5)-dianilide

3,4-dinitro-chlorobenzene
610-40-2

3,4-dinitro-chlorobenzene

A

5-chloro-2-nitroaniline
1635-61-6

5-chloro-2-nitroaniline

B

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

C

4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With tin(ll) chloride In methanol; water Title compound not separated from byproducts;A 23.66 % Chromat.
B 12.20 % Chromat.
C 11.03 % Chromat.
N-(4-chloro-2-nitrophenyl)-acetamide
881-51-6

N-(4-chloro-2-nitrophenyl)-acetamide

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2SO4
2: H2NNH2.H2O / Raney Ni
View Scheme
Multi-step reaction with 2 steps
1: aqueous sulfuric acid
2: nickel; ethanol / Hydrogenation
View Scheme
4-chloro-aniline
106-47-8

4-chloro-aniline

nitrogen

nitrogen

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2.) H2SO4/HNO3
2: H2SO4
3: H2NNH2.H2O / Raney Ni
View Scheme
5-chloro-2-nitroaniline
1635-61-6

5-chloro-2-nitroaniline

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
In diethyl ether
5-Chloro-2-[2'-(benzimidazol-5"-yl)benzimidazol-5'-yl]-benzimidazole

5-Chloro-2-[2'-(benzimidazol-5"-yl)benzimidazol-5'-yl]-benzimidazole

5-chloro-2-nitroaniline
1635-61-6

5-chloro-2-nitroaniline

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
With stannous chloride In ethanol
5-bromo-2-nitroaniline
5228-61-5

5-bromo-2-nitroaniline

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate
2: palladium on activated charcoal; ammonium formate / Reflux
View Scheme
3,4-dinitro-chlorobenzene
610-40-2

3,4-dinitro-chlorobenzene

A

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

B

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrazine hydrate In methanol at 20℃; for 0.0833333h; Overall yield = 90 %;
5-chloro-1H,3H-2,1,3-benzothiadiazole 2,2-dioxide
1615-07-2

5-chloro-1H,3H-2,1,3-benzothiadiazole 2,2-dioxide

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
With sulfuric acid; water In acetonitrile at 85℃; Kinetics; Reagent/catalyst; Temperature;
2,6-dichloro-1H-1,3-benzimidazole
4887-95-0

2,6-dichloro-1H-1,3-benzimidazole

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Conditions
ConditionsYield
With hydrazine hydrate at 110℃;
formic acid
64-18-6

formic acid

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

5-chloro-1H-benzimidazole
4887-82-5

5-chloro-1H-benzimidazole

Conditions
ConditionsYield
With hydrogenchloride In water for 3h; Reflux;100%
at 110℃; for 4h;95%
With tetrabutyl-ammonium chloride In water; toluene at 160℃; for 0.25h; Microwave irradiation;89%
4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

dimethylglyoxal
431-03-8

dimethylglyoxal

6-chloro-2,3-dimethyl-quinoxaline
17911-93-2

6-chloro-2,3-dimethyl-quinoxaline

Conditions
ConditionsYield
With zirconium(IV) chloride In methanol at 20℃; for 0.0833333h;100%
With hydrogen fluoride In water at 20℃; for 0.666667h;98%
With 1-methyl-3-(3-trimethoxysilylpropyl)imidazolium hydrogen sulfate immobilized on cellulose In water at 20℃; for 0.05h; Green chemistry;98%
Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

5-chloro-2-methyl-1H-benzimidazole
2818-69-1

5-chloro-2-methyl-1H-benzimidazole

Conditions
ConditionsYield
With zirconium(IV) chloride In methanol at 20℃; for 3h;100%
With ammonium chloride In ethanol Inert atmosphere; Reflux; Green chemistry;96%
With gallium(III) triflate at 20℃; for 0.416667h;86%
With zirconium(IV) oxychloride octahydrate for 0.116667h; Microwave irradiation;84%
With H-Y-zeolite In ethanol for 10h; Heating;74%
Boc-Aib-OH
30992-29-1

Boc-Aib-OH

(1α,5α,6α)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid
927679-54-7

(1α,5α,6α)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

C16H19ClN4O*(x)ClH

C16H19ClN4O*(x)ClH

Conditions
ConditionsYield
Stage #1: Boc-Aib-OH; 4-Chloro-1,2-phenylenediamine With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran at 20℃; for 72h;
Stage #2: With trifluoroacetic acid In dichloromethane for 2h;
Stage #3: (1α,5α,6α)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid Further stages;
100%
4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

Trichloroacetyl isocyanate
3019-71-4

Trichloroacetyl isocyanate

A

2,2,2-trichloro-N-(5-chloro-1H-benzimidazol-2-yl)acetamide

2,2,2-trichloro-N-(5-chloro-1H-benzimidazol-2-yl)acetamide

B

2,2,2-trichloro-N-(6-chloro-1H-benzimidazol-2-yl)acetamide

2,2,2-trichloro-N-(6-chloro-1H-benzimidazol-2-yl)acetamide

Conditions
ConditionsYield
In dichloromethane at -10 - 20℃; Overall yield = 85 %;A 100%
B n/a
C12H15IO2
1083427-54-6

C12H15IO2

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

C30H33ClI2N2O2

C30H33ClI2N2O2

Conditions
ConditionsYield
In ethanol at 80℃; for 8h; Inert atmosphere;100%
4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

benzil
134-81-6

benzil

2,3-diphenyl-6-chloroquinoxaline
36305-60-9

2,3-diphenyl-6-chloroquinoxaline

Conditions
ConditionsYield
With ZnO-loaded mesoporous silica (KIT-6) (aged at 130 °C and containing 10 wt% ZnO) In methanol at 20℃; for 0.166667h;99%
With sulfated titania (TiO2-SO42-) In ethanol at 20℃; for 0.75h;98.5%
With hydrogen fluoride In water at 20℃; for 0.75h;98%
4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

5-chlorobenzotriazole
94-97-3

5-chlorobenzotriazole

Conditions
ConditionsYield
With K10 Montmorillonite Clay; sodium nitrite In neat (no solvent, solid phase) at 110℃; for 1h; Microwave irradiation; Green chemistry;99%
With tert.-butylnitrite In acetonitrile at 27 - 29℃; for 0.25h;97%
With acetic acid In water at 70 - 80℃; for 0.416667h;86%
4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

acetone
67-64-1

acetone

7-chloro-2,2,4-trimethyl-2,3-dihydro-1H-benzo[b][1,4]diazepine

7-chloro-2,2,4-trimethyl-2,3-dihydro-1H-benzo[b][1,4]diazepine

Conditions
ConditionsYield
With ZnPcOC6F5-APTES(at)SiO2 at 20℃; for 0.416667h; Catalytic behavior;99%
With silica gel-supported sulfuric acid In acetonitrile at 20℃; for 0.833333h;94%
at 26 - 30℃; for 3.5h; Ionic liquid;90%
4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

3-bromo-4-fluorobenzaldehyde
77771-02-9

3-bromo-4-fluorobenzaldehyde

C14H9BrClFN2

C14H9BrClFN2

Conditions
ConditionsYield
With C23H3BF16N2O In toluene at 25℃; for 3h; Green chemistry;99%
phenylacetic acid
103-82-2

phenylacetic acid

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

2-benzyl-5-chloro-1H-benzo[d]imidazole
7118-63-0

2-benzyl-5-chloro-1H-benzo[d]imidazole

Conditions
ConditionsYield
With hydrogenchloride for 7.5h; Heating;98%
With boric acid In 5,5-dimethyl-1,3-cyclohexadiene for 16h; Reflux;65%
With hydrogenchloride at 150 - 160℃;
hydrogenchloride at 110 - 130℃;
4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

6-chloroquinoxaline-2,3(1H,4H)-dione
6639-79-8

6-chloroquinoxaline-2,3(1H,4H)-dione

Conditions
ConditionsYield
for 16h; Heating;98%
Reflux;96%
Reflux;96%
benzaldehyde
100-52-7

benzaldehyde

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

5-chloro-2-phenyl-1H-benzimidazole
4926-65-2

5-chloro-2-phenyl-1H-benzimidazole

Conditions
ConditionsYield
With oxygen; cobalt(II) hydroxide In ethanol at 20℃; for 4h;98%
With sodium metabisulfite In N,N-dimethyl acetamide at 100℃; for 2h;95.8%
With ferric hydrogen sulphate In ethanol at 20℃; for 0.833333h; chemoselective reaction;90%
4,4'-dibromobenzil
35578-47-3

4,4'-dibromobenzil

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

2,3-bis(4-bromophenyl)-6-chloroquinoxaline
1094618-65-1

2,3-bis(4-bromophenyl)-6-chloroquinoxaline

Conditions
ConditionsYield
With heteropoly-12-tungstophosphoric acid 40% H3[PW12O40]*12H2O supported on graphitic carbon nitride (g-C3N4) In water at 20℃; for 0.5h; Green chemistry;98%
With titanium silicate In methanol at 20℃; for 1h;95%
With niobium pentachloride In ethanol at 20℃; for 0.05h;93%
With 2-methylenesuccinic acid In water at 20℃; for 1h; Schlenk technique; Green chemistry;85%
1,10-phenanthroline-5,6-dione
27318-90-7

1,10-phenanthroline-5,6-dione

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

11-chloro-dipyrido[3,2-a:2′,3′-c]phenazine
511243-54-2

11-chloro-dipyrido[3,2-a:2′,3′-c]phenazine

Conditions
ConditionsYield
With sulfated titania (TiO2-SO42-) In ethanol at 20℃; for 0.166667h;98%
With sulfate loaded TiO2 for 0.05h; Microwave irradiation; Neat (no solvent);98%
With sulfated TiO2-P25 (Degussa titania) for 0.0583333h; Microwave irradiation; Neat (no solvent);97%
Glyoxal
131543-46-9

Glyoxal

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

6-chloroquinoxaline
5448-43-1

6-chloroquinoxaline

Conditions
ConditionsYield
With hydrogen fluoride In water at 20℃; for 0.75h;98%
In water at 20℃; for 0.5h; Green chemistry;92%
In water at 20℃; for 1h;90%
With sodium metabisulfite; sodium hydrogen sulfate In water at 70℃;
1,2-bis(4-fluorophenyl)ethane-1,2-dione
579-39-5

1,2-bis(4-fluorophenyl)ethane-1,2-dione

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

2,3-bis-(4-fluorophenyl)-6-chloroquinoxaline
361149-74-8

2,3-bis-(4-fluorophenyl)-6-chloroquinoxaline

Conditions
ConditionsYield
With hydrogen fluoride In water at 20℃; for 0.5h;98%
With titanium silicate In methanol at 20℃; for 1h;98%
With sodium bromate; sodium hydrogensulfite In water at 20℃;0.48 g
4-methoxybenzil
22711-21-3

4-methoxybenzil

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

6-chloro-2-(4-methoxyphenyl)-3-phenylquinoxaline

6-chloro-2-(4-methoxyphenyl)-3-phenylquinoxaline

Conditions
ConditionsYield
With acetic acid In ethanol at 22 - 25℃; for 1h; Irradiation;98%
4,4'-bis(trifluoromethyl)benzil
73790-20-2

4,4'-bis(trifluoromethyl)benzil

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

6-chloro-2,3-bis(4-(trifluoromethyl)phenyl)quinoxaline

6-chloro-2,3-bis(4-(trifluoromethyl)phenyl)quinoxaline

Conditions
ConditionsYield
With hydrogen fluoride In water at 20℃; for 0.5h;98%
5-iodovaniline
5438-36-8

5-iodovaniline

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

4'-(5-chloro-1H-benzo[d]imidazole-2-yl)-2'-iodo-6'-methoxyphenol

4'-(5-chloro-1H-benzo[d]imidazole-2-yl)-2'-iodo-6'-methoxyphenol

Conditions
ConditionsYield
With sodium metabisulfite In ethanol; water at 20℃; for 2h;98%
With sodium metabisulfite In N,N-dimethyl-formamide for 4h; Reflux;85.1%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

5-chloro-2-(thiophen-2-yl)-1H-benzo[d]imidazole
27503-77-1

5-chloro-2-(thiophen-2-yl)-1H-benzo[d]imidazole

Conditions
ConditionsYield
With polyamine dendrimer with glycerol initiated polyepichlorohydrin; air In ethanol at 20℃; for 0.05h;97%
With sodium metabisulfite In N,N-dimethyl-formamide at 130℃; for 0.2h; Microwave irradiation;67.8%
With bentonite clay In acetonitrile at 20℃; for 1h;64%
In nitrobenzene
With copper diacetate In methanol Heating;
furfural
98-01-1

furfural

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

5-Chloro-2-furan-2-yl-1-furan-2-ylmethyl-1H-benzoimidazole
79324-86-0

5-Chloro-2-furan-2-yl-1-furan-2-ylmethyl-1H-benzoimidazole

Conditions
ConditionsYield
With hydrogenchloride In methanol; water for 6h;97%
4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

7-chloro-3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline
88075-40-5

7-chloro-3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline

Conditions
ConditionsYield
In ethanol at 20℃; for 0.5h;97%
In methanol Ambient temperature;83.2%
In 1,4-dioxane Heating;
furil
492-94-4

furil

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

6-chloro-2,3-di(furan-2-yl)-quinoxaline
70976-04-4

6-chloro-2,3-di(furan-2-yl)-quinoxaline

Conditions
ConditionsYield
With gallium(III) triflate In ethanol at 20℃; for 0.166667h;97%
In methanol; acetic acid at 160℃; for 0.0833333h; Irradiation;95%
With 1-(propyl-3-sulfonate) 3-methylimidazol(3H)-1-ium phosphotungstate In water at 20℃; for 0.2h; Reagent/catalyst; Time;94%
4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

1,2-bis(4-methoxyphenyl)-1,2-ethanedione
1226-42-2

1,2-bis(4-methoxyphenyl)-1,2-ethanedione

6-chloro-2,3-bis(4-methoxyphenyl)quinoxaline

6-chloro-2,3-bis(4-methoxyphenyl)quinoxaline

Conditions
ConditionsYield
With zirconium(IV) chloride In methanol at 20℃; for 2h;97%
With silica-supported stannous chloride In methanol at 20℃; for 1h;97%
With silica-supported bismuth(III) chloride In methanol at 20℃; for 1.5h; Catalytic behavior;95%
benzaldehyde
100-52-7

benzaldehyde

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

6‐chloro‐2‐phenyl‐1H-benzoimidazole
4926-65-2

6‐chloro‐2‐phenyl‐1H-benzoimidazole

Conditions
ConditionsYield
With [3-(1-methylimidazolium-3-yl)propane-1-sulfonate]3PW12O40; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 40℃; for 10h;97%
With water extract of onion In ethanol; water at 20℃; for 12h; Green chemistry;91%
With sulfonated graphene oxide (GO-HSO3) In neat (no solvent) at 20℃; for 7h; chemoselective reaction;81%
With AlKIT-5 In acetonitrile for 6h; Reflux;80%
Reflux;64%
aminoiminomethanesulfonic acid
1184-90-3

aminoiminomethanesulfonic acid

4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

5-chloro-1H-benzo[d]imidazol-2-amine
5418-93-9

5-chloro-1H-benzo[d]imidazol-2-amine

Conditions
ConditionsYield
at 60℃;97%

4-Chloro-1,2-diaminobenzene Chemical Properties

IUPAC Name: 4-Chlorobenzene-1,2-diamine
Synonyms of 4-Chloro-1,2-diaminobenzene (CAS NO.95-83-0): 1,2-Benzenediamine, 4-chloro- ; 4-Chlorbenzol-1,2-diamin ; 4-Chloro-1,2-benzenediamine ; 4-Chloro-1,2-diaminobenzene ; 4-Chlorobenzene-1,2-diamine
Molecular Structure :
Molecular Formula: C6H7ClN2
Molecular Weight : 142.59
CAS NO: 95-83-0
EINECS : 202-456-8 
H bond acceptors: 2
H bond donors: 4
Freely Rotating Bonds: 2
Polar Surface Area: 6.48 Å2 
Molar Refractivity: 39.62 cm3
Molar Volume: 105.9 cm3
Index of Refraction:1.67
Surface Tension: 59.9 dyne/cm
Density: 1.345 g/cm3
Flash Point: 135.4 °C
Enthalpy of Vaporization: 54.03 kJ/mol
Boiling Point: 300.2 °C at 760 mmHg
Vapour Pressure: 0.00114 mmHg at 25°C
Melting point : 70-75°C
Water solubility : 16 g/L (20°C)
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
Appearance: 4-Chloro-1,2-diaminobenzene (CAS NO.95-83-0) is brown crystalline solid or powder.
SMILES: Clc1cc(N)c(N)cc1
InChI: InChI=1/C6H7ClN2/c7-4-1-2-5(8)6(9)3-4/h1-3H,8-9H2
InChIKey: BXIXXXYDDJVHDL-UHFFFAOYAR
Std. InChI: InChI=1S/C6H7ClN2/c7-4-1-2-5(8)6(9)3-4/h1-3H,8-9H2
Std. InChIKey: BXIXXXYDDJVHDL-UHFFFAOYSA-N

4-Chloro-1,2-diaminobenzene Production

Raw materials :Etanol-->Sodium hydroxide-->Diethyl ether-->Stannous chloride dihydrate-->5-Chloro-2-nitroaniline
Preparation Products :Vat Brown 5R

4-Chloro-1,2-diaminobenzene Toxicity Data With Reference

1.    

mma-sat 10 µg/plate

    ENMUDM    Environmental Mutagenesis. 7 (Suppl 5)(1985),1.
2.    

mma-esc 1 mg/plate

    ENMUDM    Environmental Mutagenesis. 7 (Suppl 5)(1985),1.
3.    

dnd-hmn:fbr 50 µmol/L

    MUREAV    Mutation Research. 127 (1984),107.
4.    

cyt-mus-ipr 100 mg/kg

    ENMUDM    Environmental Mutagenesis. 8 (Suppl 6)(1986),53.
5.    

orl-rat TDLo:135 g/kg/77 W-C:CAR

    CRNGDP    Carcinogenesis. 1 (1980),495.

4-Chloro-1,2-diaminobenzene Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 27 , 1982,p. 81.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 27 , 1982,p. 81.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-63 ,1978. . Reported in EPA TSCA Inventory.

4-Chloro-1,2-diaminobenzene Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 36/37/38-40
R36/37/38: Irritating to eyes, respiratory system and skin. 
R40: Limited evidence of a carcinogenic effect.
Safety Statements: 26-36/37
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37: Wear suitable protective clothing and gloves.
RIDADR: 2811
WGK Germany: 3
RTECS: SS8850000
F: 8
Hazard Note: Irritant

4-Chloro-1,2-diaminobenzene Specification

1.Air & Water Reactions: 4-Chloro-1,2-diaminobenzene may be sensitive to prolonged exposure to air and light. Insoluble in water.
2.Reactivity Profile : 4-Chloro-1,2-diaminobenzene (CAS NO.95-83-0) is incompatible with strong oxidizers. 4-Chloro-1,2-diaminobenzene reacts with alpha-ketoacids to form quinoxalones.

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