Product Name

  • Name

    4-Chloro-2-nitroaniline

  • EINECS 201-925-4
  • CAS No. 89-63-4
  • Article Data82
  • CAS DataBase
  • Density 1.494 g/cm3
  • Solubility insoluble in water
  • Melting Point 115-119 °C
  • Formula C6H5ClN2O2
  • Boiling Point 308.8 °C at 760 mmHg
  • Molecular Weight 172.571
  • Flash Point 140.5 °C
  • Transport Information UN 2237 6.1/PG 3
  • Appearance bright orange powder
  • Safety 28-36/37-45-61-28A
  • Risk Codes 26/27/28-33-51/53
  • Molecular Structure Molecular Structure of 89-63-4 (4-Chloro-2-nitroaniline)
  • Hazard Symbols VeryT+, DangerousN, ToxicT
  • Synonyms Aniline,4-chloro-2-nitro- (8CI);(4-Chloro-2-nitrophenyl)amine;1-Amino-2-nitro-4-chlorobenzene;2-Nitro-4-chloroaniline;4-Chloro-2-nitrobenzenamine;Daito Red Base 3GL;Devol Red F;Diazo Fast Red 3GL;Fast Red 3GL Base;Fast Red3GL Special Base;Hiltonil Fast Red 3GL Base;Mitsui Red 3GL Base;NSC 3546;NaphtoelanFast Red 3GL Base;PCON;PCONA;Red Base Ciba VI;Red Base Irga VI;Shinnippon Fast Red 3GL Base;p-Chloro-o-nitroaniline;
  • PSA 71.84000
  • LogP 2.93480

Synthetic route

2-nitro-aniline
88-74-4

2-nitro-aniline

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.0833333h; Green chemistry;99.2%
With copper dichloride; 1-hexyl-3-methylimidazol-1-ium chloride at 40℃; for 16h; regioselective reaction;85%
With N-chloro-succinimide In acetonitrile for 10h; Heating;57%
Multi-step reaction with 2 steps
1: diethyl ether; hypochlorous acid / 20 °C
2: hydrochloric acid; diethyl ether / -20 °C
View Scheme
3,4-dinitro-chlorobenzene
610-40-2

3,4-dinitro-chlorobenzene

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol; water at 20℃; for 4h; Green chemistry;90%
4-chloro-aniline
106-47-8

4-chloro-aniline

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 3h;92%
Multi-step reaction with 3 steps
1: acetic acid / 0.25 h / Heating
2: 60percent nitric acid, conc. sulfuric acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min
3: conc. sulfuric acid / 0.25 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane
2: nitric acid; acetic anhydride / dichloromethane
3: hydrogenchloride / water / Reflux
View Scheme
N-(4-chloro-2-nitrophenyl) pyrimidin-2-amine

N-(4-chloro-2-nitrophenyl) pyrimidin-2-amine

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
Stage #1: N-(4-chloro-2-nitrophenyl) pyrimidin-2-amine With triethylsilane; trifluoroacetic acid at 50℃; Inert atmosphere;
Stage #2: With acetic acid; hydrazine In methanol at 20℃; Inert atmosphere; regioselective reaction;
80%
3-chloro-aniline
108-42-9

3-chloro-aniline

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With nitric acid In sulfuric acid; acetic acid at 20 - 25℃; for 10.5h; Temperature;
3-Chloronitrobenzene
121-73-3

3-Chloronitrobenzene

A

2-chloro-6-nitroaniline
769-11-9

2-chloro-6-nitroaniline

B

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

4-Chloro-2-nitroaniline

C

2-Chloro-4-nitroaniline
121-87-9

2-Chloro-4-nitroaniline

Conditions
ConditionsYield
With 2,4,6-trichlorosulfenamide; potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.333333h;A 26%
B 7%
C 38%
With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride In N,N-dimethyl-formamide for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide In dimethyl sulfoxide Ambient temperature; Yield given. Yields of byproduct given;
With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride In N,N-dimethyl-formamide at 20℃; Substitution; Amination; Title compound not separated from byproducts;
N-(2-nitro-4-chlorophenyl)benzamide
52010-24-9

N-(2-nitro-4-chlorophenyl)benzamide

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 12h;99%
N-(4-chloro-2-nitrophenyl)-acetamide
881-51-6

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

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With sulfuric acid
With hydrogenchloride
With sodium methylate
o-azidonitrobenzene
1516-58-1

o-azidonitrobenzene

A

2-chloro-6-nitroaniline
769-11-9

2-chloro-6-nitroaniline

B

2-nitro-aniline
88-74-4

2-nitro-aniline

C

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With boron trichloride In benzene Ambient temperature;A 17%
B 3%
C 64%
With boron trichloride In benzene at 50℃; for 6h;A 3%
B 3%
C 64%
With boron trichloride In benzene at 50℃; for 6h;A 17%
B 3%
C 64%
N-(4-chlorophenyl)acetamide
539-03-7

N-(4-chlorophenyl)acetamide

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With nitric acid Kochen des Reaktionsproduktes mit Natronlauge;
With nitric acid at -10℃; durch Erwaermen des Reaktionsprodukts mit etwas konz. Schwefelsaeure auf 100grad;
Multi-step reaction with 2 steps
1: 60percent nitric acid, conc. sulfuric acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min
2: conc. sulfuric acid / 0.25 h / 100 °C
View Scheme
2-nitro-aniline
88-74-4

2-nitro-aniline

A

2-chloro-6-nitroaniline
769-11-9

2-chloro-6-nitroaniline

B

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With trichloroisocyanuric acid; brilliant green carbocation In acetonitrile at 20℃; for 1.5h; Irradiation; Overall yield = 94 %; Overall yield = 81.1 mg; regioselective reaction;
2-(4-chloro-2-nitrophenylamino)ethanol
59320-13-7

2-(4-chloro-2-nitrophenylamino)ethanol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
In pyridine; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate
2,5-dichloronitrobenzene
89-61-2

2,5-dichloronitrobenzene

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With ammonia; water at 175℃; im Eisen-Autoklaven;
With ethanol; ammonia at 165℃;
With ethanol; ammonia at 200 - 220℃;
With NH2
(4-chloro-phenyl)-pyrimidin-2-yl-amine

(4-chloro-phenyl)-pyrimidin-2-yl-amine

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: palladium diacetate; silver(I) nitrite; dipotassium peroxodisulfate; acetic acid / 1,2-dichloro-ethane / 80 °C / Inert atmosphere
2.1: trifluoroacetic acid; triethylsilane / 50 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
View Scheme
4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

A

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

5-chloro-2-nitroaniline

B

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h; Overall yield = 93 %;A 49 %Chromat.
B 51 %Chromat.
1-azido-4-methyl-2-nitrobenzene
89284-67-3

1-azido-4-methyl-2-nitrobenzene

A

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

4-Chloro-2-nitroaniline

B

6-chlorobenzo[c][1,2,5]oxadiazole 1-oxide
39060-31-6

6-chlorobenzo[c][1,2,5]oxadiazole 1-oxide

C

1-(4-Chloro-2-nitro-phenyl)-5-ethoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester
210989-45-0

1-(4-Chloro-2-nitro-phenyl)-5-ethoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
With diethyl acetylmalonate; sodium ethanolate In ethanol for 5h; Ambient temperature;A 35%
B 27%
C 25%
N-(4-chlorophenyl)acetamide
539-03-7

N-(4-chlorophenyl)acetamide

A

N-(4-chloro-2-nitrophenyl)-acetamide
881-51-6

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

B

N-(4-chloro-3-nitrophenyl)acetamide
5540-60-3

N-(4-chloro-3-nitrophenyl)acetamide

C

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With sodium nitrate; sulfuric acid for 3h; Ambient temperature;A 62%
B 9%
C 21%
1-azido-4-methyl-2-nitrobenzene
89284-67-3

1-azido-4-methyl-2-nitrobenzene

diethyl 1,3-acetonedicarboxylate
105-50-0

diethyl 1,3-acetonedicarboxylate

A

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

4-Chloro-2-nitroaniline

B

6-chlorobenzo[c][1,2,5]oxadiazole 1-oxide
39060-31-6

6-chlorobenzo[c][1,2,5]oxadiazole 1-oxide

C

1-(4-Chloro-2-nitro-phenyl)-5-ethoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester
210989-45-0

1-(4-Chloro-2-nitro-phenyl)-5-ethoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 5h; Ambient temperature;A 35%
B 27%
C 25%
N,N-dichloro-2-nitroaniline
59483-70-4

N,N-dichloro-2-nitroaniline

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With hydrogenchloride; diethyl ether at -20℃;
2,5-dichloronitrobenzene
89-61-2

2,5-dichloronitrobenzene

ammonium carbonate

ammonium carbonate

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With basic copper carbonate powder; ethylene glycol at 130 - 140℃;
N-(4-chlorophenyl)benzamide
2866-82-2

N-(4-chlorophenyl)benzamide

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nitric acid; copper(II) nitrate hydrate; oxygen / acetonitrile; water / 12 h / 100 °C / 760.05 Torr
2: potassium hydroxide / methanol / 12 h / 20 °C
View Scheme
4-chloro-aniline
106-47-8

4-chloro-aniline

A

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

B

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With sulfuric acid; nitric acid at -20℃;
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-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With titanium(III) chloride In methanol; water Title compound not separated from byproducts;A 19.10 % Chromat.
B 15.90 % Chromat.
tert-butylhypochlorite
507-40-4

tert-butylhypochlorite

2-nitro-aniline
88-74-4

2-nitro-aniline

A

2-chloro-6-nitroaniline
769-11-9

2-chloro-6-nitroaniline

B

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With tert-butyl alcohol; benzene
With acetic acid; benzene
With benzene
With tert-butyl alcohol
With acetic acid
dibutyl ether
142-96-1

dibutyl ether

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

A

1-Butoxy-butane; compound with trifluoro-methanesulfonic acid

1-Butoxy-butane; compound with trifluoro-methanesulfonic acid

B

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔH, ΔS;
1,1,3,3-Tetramethyldisiloxane
3277-26-7

1,1,3,3-Tetramethyldisiloxane

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

A

Trifluoro-methanesulfonic acid; compound with 1,1,3,3-tetramethyl-disiloxane

Trifluoro-methanesulfonic acid; compound with 1,1,3,3-tetramethyl-disiloxane

B

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔS, ΔH;
Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

A

1,1,1,3,3,3-Hexamethyl-disiloxane; compound with trifluoro-methanesulfonic acid

1,1,1,3,3,3-Hexamethyl-disiloxane; compound with trifluoro-methanesulfonic acid

B

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔH, ΔS;
Octamethyltrisiloxane
107-51-7

Octamethyltrisiloxane

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

A

C8H24O2Si3*CHF3O3S

C8H24O2Si3*CHF3O3S

B

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔH, ΔS;
Hexamethylcyclotrisiloxane
541-05-9

Hexamethylcyclotrisiloxane

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

A

2,2,4,4,6,6-Hexamethyl-[1,3,5,2,4,6]trioxatrisilinane; compound with trifluoro-methanesulfonic acid

2,2,4,4,6,6-Hexamethyl-[1,3,5,2,4,6]trioxatrisilinane; compound with trifluoro-methanesulfonic acid

B

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔH, ΔS;
methyltrimethicone
17928-28-8

methyltrimethicone

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid

A

C10H30O3Si4*CHF3O3S

C10H30O3Si4*CHF3O3S

B

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

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔH, ΔG;
4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

dimethyl sulfate
77-78-1

dimethyl sulfate

4-chloro-N-methyl-2-nitroaniline
15950-17-1

4-chloro-N-methyl-2-nitroaniline

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; toluene at 20℃; Methylation;100%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water; toluene at 20℃;94%
4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

2-bromo-4-chloro-6-nitrobenzenamine
827-25-8

2-bromo-4-chloro-6-nitrobenzenamine

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile Reflux;100%
With bromine; acetic acid at 0 - 20℃; for 1h;100%
With bromine; acetic acid at 0 - 20℃; for 1h; Cooling with ice;100%
(3R)-4-[2-chloro-6-(1-methanesulfonylcyclopropyl)pyrimidin-4-yl]-3-methylmorpholine
1233339-68-8

(3R)-4-[2-chloro-6-(1-methanesulfonylcyclopropyl)pyrimidin-4-yl]-3-methylmorpholine

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

4-Chloro-2-nitroaniline

(R)-N-(4-chloro-2-nitrophenyl)-4-(3-methylmorpholino)-6-(1-(methylsulfonyl)cyclopropyl)pyrimidin-2-amine

(R)-N-(4-chloro-2-nitrophenyl)-4-(3-methylmorpholino)-6-(1-(methylsulfonyl)cyclopropyl)pyrimidin-2-amine

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; for 1h; Buchwald-Hartwig Coupling; Microwave irradiation; Sealed tube; Inert atmosphere;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

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

4-Chloro-2-nitroaniline

2-nitro-4-thiophen-2-yl-phenylamine
405170-93-6

2-nitro-4-thiophen-2-yl-phenylamine

Conditions
ConditionsYield
With potassium phosphate; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate In 1,4-dioxane; water for 20h; Sealed tube; Schlenk technique; Inert atmosphere;100%
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%
trimethylsilyl acetate
2754-27-0

trimethylsilyl acetate

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

4-Chloro-2-nitroaniline

N-(4-chloro-2-nitrophenyl)-acetamide
881-51-6

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

Conditions
ConditionsYield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;99%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;99%
trimethylsilyl isobutyrate
16883-61-7

trimethylsilyl isobutyrate

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

4-Chloro-2-nitroaniline

4'-chloro-2-methyl-2'-nitropropananilide
86569-53-1

4'-chloro-2-methyl-2'-nitropropananilide

Conditions
ConditionsYield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;99%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;99%
trimethylsilyl 2,2-dimethylpropionate
37170-49-3

trimethylsilyl 2,2-dimethylpropionate

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

4-Chloro-2-nitroaniline

4'-chloro-2,2-dimethyl-2'-nitropropananilide

4'-chloro-2,2-dimethyl-2'-nitropropananilide

Conditions
ConditionsYield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;99%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;99%
3-methylbutyric acid trimethylsilyl ester
55557-13-6

3-methylbutyric acid trimethylsilyl ester

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

4-Chloro-2-nitroaniline

4'-chloro-3-methyl-2'-nitrobutananilide

4'-chloro-3-methyl-2'-nitrobutananilide

Conditions
ConditionsYield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;99%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;99%
4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

β-naphthol
135-19-3

β-naphthol

1-(4'-chloro-2'-nitrophenylazo)-2-naphthol
6410-13-5

1-(4'-chloro-2'-nitrophenylazo)-2-naphthol

Conditions
ConditionsYield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h;
Stage #2: β-naphthol In water at 60℃; for 1h;
99%
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Green chemistry;
Stage #2: β-naphthol In water at 60℃; for 1h; Green chemistry;
99%
With hydrogenchloride; sodium nitrite 1.) -10 deg C - 0 deg C, 5 min, 2.) EtOH, H2O; Yield given. Multistep reaction;
With hydrogenchloride; Amberlite-IR 120 (Na(1+) form); sodium nitrite 1.) 0-5 deg C, 2.) water, ethanol, RT, 30 min; Yield given. Multistep reaction;
2,5-dimethyl-2,3-dihydrofuran-3-one
14400-67-0

2,5-dimethyl-2,3-dihydrofuran-3-one

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

4-Chloro-2-nitroaniline

2,5-dimethyl-2-(4-chloro-2-nitrophenylazo)-3-oxo-2,3-dihydrofuran

2,5-dimethyl-2-(4-chloro-2-nitrophenylazo)-3-oxo-2,3-dihydrofuran

Conditions
ConditionsYield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite at 20℃; for 1h;
Stage #2: 2,5-dimethyl-2,3-dihydrofuran-3-one In water at 20℃; for 1h;
99%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

4-Chloro-2-nitroaniline

tert-butyl N-[(tert-butoxy)carbonyl]-N-(4-chloro-2-nitrophenyl)carbamate
1040363-35-6

tert-butyl N-[(tert-butoxy)carbonyl]-N-(4-chloro-2-nitrophenyl)carbamate

Conditions
ConditionsYield
dmap In tetrahydrofuran at 90℃; for 1h;99%
With dmap In tetrahydrofuran at 25 - 90℃; for 6h;58%
4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

isobutyraldehyde
78-84-2

isobutyraldehyde

4-chloro-2-nitro-N-(2-methyl-1-propen-1-yl)benzenamine
424799-62-2

4-chloro-2-nitro-N-(2-methyl-1-propen-1-yl)benzenamine

Conditions
ConditionsYield
With 4 A molecular sieve In benzene at 20℃; for 26h;99%
Molecular sieve;
With magnesium sulfate In dichloromethane Schlenk technique; Inert atmosphere; Reflux; Sealed tube;
2'-methoxyacetoacetanilide
92-15-9

2'-methoxyacetoacetanilide

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

4-Chloro-2-nitroaniline

pigment yellow 73
13515-40-7

pigment yellow 73

Conditions
ConditionsYield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h;
Stage #2: 2'-methoxyacetoacetanilide In water at 60℃; for 1h;
99%
5-acetoacetylamino-2-benzimidazolone

5-acetoacetylamino-2-benzimidazolone

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

4-Chloro-2-nitroaniline

pigment orange 36

pigment orange 36

Conditions
ConditionsYield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.416667h;
Stage #2: 5-acetoacetylamino-2-benzimidazolone In water at 60℃; for 2h; Time;
99%
N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

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

4-Chloro-2-nitroaniline

pigment yellow 6
4106-76-7

pigment yellow 6

Conditions
ConditionsYield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water for 0.666667h;
Stage #2: N-phenylacetoacetamide In water at 20℃; for 0.166667h;
99%
trimethylsilyl 2-methylbenzoate
55557-15-8

trimethylsilyl 2-methylbenzoate

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

4-Chloro-2-nitroaniline

4'-chloro-2-methyl-2'-nitrobenzanilide

4'-chloro-2-methyl-2'-nitrobenzanilide

Conditions
ConditionsYield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;98%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;98%
4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

ethyl chlorocarbonylacetate
36239-09-5

ethyl chlorocarbonylacetate

ethyl 3-((4-chloro-2-nitrophenyl)amino)-3-oxopropanoate
143948-68-9

ethyl 3-((4-chloro-2-nitrophenyl)amino)-3-oxopropanoate

Conditions
ConditionsYield
In dichloromethane at 20℃;98%
In toluene for 24h; Heating;63%
1,2-dibromo-1,2-diphenylethane
13440-24-9

1,2-dibromo-1,2-diphenylethane

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

4-Chloro-2-nitroaniline

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

2,3-diphenyl-6-chloroquinoxaline

Conditions
ConditionsYield
With N-hexylpyridine hexafluorophosphate; cisplatine; 4,7-Dimethyl-1,10-phenanthroline; diisopropanolamine In dimethyl sulfoxide at 80℃; for 12h; Reagent/catalyst; Inert atmosphere;97.3%
4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

chloroacetyl chloride
79-04-9

chloroacetyl chloride

N-(4-chloro-2-nitrophenyl)-2-chloroacetamide
40930-49-2

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

Conditions
ConditionsYield
In N,N-dimethyl-formamide Cooling with ice;97%
trimethylsilyl ester of hydrocinnamic acid
21273-15-4

trimethylsilyl ester of hydrocinnamic acid

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

4-Chloro-2-nitroaniline

4'-chloro-2'-nitro-3-phenylpropananilide

4'-chloro-2'-nitro-3-phenylpropananilide

Conditions
ConditionsYield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;97%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;97%
4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

2,6-difluorobenzoylchloride
18063-02-0

2,6-difluorobenzoylchloride

N,N-bis-(2,6-difluorobenzoyl)-4-chloro-6-nitroaniline
212503-94-1

N,N-bis-(2,6-difluorobenzoyl)-4-chloro-6-nitroaniline

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 20℃;97%
formic acid
64-18-6

formic acid

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

4-Chloro-2-nitroaniline

N-(4-Chloro-2-nitro-phenyl)-formamide

N-(4-Chloro-2-nitro-phenyl)-formamide

Conditions
ConditionsYield
With Hexamethyldisiloxane; MS-5Angstroem; 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;96%
4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

3-Chloronitrobenzene
121-73-3

3-Chloronitrobenzene

Conditions
ConditionsYield
With tetrahydrofuran; tert.-butylnitrite; dimethyl sulfoxide at 30℃; for 1h; Green chemistry;96%
benzyl bromide
100-39-0

benzyl bromide

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

4-Chloro-2-nitroaniline

N-benzyl-4-chloro-2-nitrobenzenamine
10066-18-9

N-benzyl-4-chloro-2-nitrobenzenamine

Conditions
ConditionsYield
In water at 100℃; for 1.5h;95%
In water at 100℃;85%
In water at 100℃; for 2h; Green chemistry;85%
nitratocarbonylbis(triphenylphosphine)rhodium
22654-78-0, 99664-53-6

nitratocarbonylbis(triphenylphosphine)rhodium

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

4-Chloro-2-nitroaniline

RhCO(P(C6H5)3)2HNC6H3ClNO2

RhCO(P(C6H5)3)2HNC6H3ClNO2

Conditions
ConditionsYield
With KOH In methanol; acetone to an acetone soln. of Rh complex were added equimolar quantity of nitroaniline (in acetone) and KOH in MeOH; solvents were evpd. in vac., red residue extd. with benzene and filtered from KNO3; solvent removed in vac., crystals pptd. with hexane, filtered, washed with hexane and dried in air; elem. anal.;95%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

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

4-Chloro-2-nitroaniline

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

diethyl (4-chloro-2-nitrophenylamino)(4-hydroxyphenyl)methylphosphonate
1296865-37-6

diethyl (4-chloro-2-nitrophenylamino)(4-hydroxyphenyl)methylphosphonate

Conditions
ConditionsYield
With ethylammonium nitrate at 20℃; for 4h;95%
4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

2.3-butanediol
513-85-9

2.3-butanediol

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

6-chloro-2,3-dimethyl-quinoxaline

Conditions
ConditionsYield
With cesiumhydroxide monohydrate; C17H14Br2CoN4 In toluene at 150℃; for 24h; Sealed tube; Inert atmosphere;95%
With sodium hydroxide In toluene at 120℃; for 3h; Inert atmosphere; Sealed tube; Green chemistry;77%
With dodecacarbonyl-triangulo-triruthenium; cesiumhydroxide monohydrate; 1,3-bis-(diphenylphosphino)propane In tert-Amyl alcohol at 150℃; for 8h; Schlenk technique; Inert atmosphere;68%
With 1,10-Phenanthroline; cesiumhydroxide monohydrate; nickel dibromide In toluene at 150℃; for 24h; Inert atmosphere; Sealed tube;64%
With cobalt supported on N,P co-doped porous carbon In toluene at 140℃; for 12h; Sealed tube; Inert atmosphere;81 %Chromat.

4-Chloro-2-nitroaniline Consensus Reports

Reported in EPA TSCA Inventory.

4-Chloro-2-nitroaniline Specification

The IUPAC name of Kayaku Fast Red 3GL Base is 4-chloro-2-nitroaniline. With the CAS registry number 89-63-4, it is also named as Azofix Red 3GL Salt. The product's categories are Intermediates of Dyes and Pigments; Anilines, Aromatic Amines and Nitro Compounds; Organics. It is bright orange powder which is insoluble in water, soluble in alcohol, ether and acetic acid, and slightly soluble in crude gasoline. It is also stable, combustible and incompatible with strong oxidizing agents. When heated to decomposition it emits toxic vapors of NOx and Cl. What's more, this chemical can form explosive products on reaction with nitric acid. So the storage environment should be well-ventilated, low-temperature and dry. Keep Kayaku Fast Red 3GL Base separate from raw materials of food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.74; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.74; (4)ACD/LogD (pH 7.4): 2.74; (5)ACD/BCF (pH 5.5): 71.65; (6)ACD/BCF (pH 7.4): 71.65; (7)ACD/KOC (pH 5.5): 740.59; (8)ACD/KOC (pH 7.4): 740.59; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.646; (13)Molar Refractivity: 41.92 cm3; (14)Molar Volume: 115.5 cm3; (15)Polarizability: 16.62×10-24 cm3; (16)Surface Tension: 62.2 dyne/cm; (17)Enthalpy of Vaporization: 54.95 kJ/mol; (18)Vapour Pressure: 0.000667 mmHg at 25°C; (19)Exact Mass: 172.003955; (20)MonoIsotopic Mass: 172.003955; (21)Topological Polar Surface Area: 71.8; (22)Heavy Atom Count: 11; (23)Complexity: 159.

Preparation of Kayaku Fast Red 3GL Base:  It can be obtained by forcing ammonolysis of 2,5-Dichloronitrobenzene.

 

Uses of Kayaku Fast Red 3GL Base: It is used in the production of yellow pigment 10G, disperse yellow 211, UV absorber UV-326 and so on. It is not only used in dyeing cotton and printing cotton, but also used for dyeing of viscose fiber, silk and polyester. What's more, it can react with sulfuric acid dimethyl ester to get 4-chloro-N-methyl-2-nitro-aniline. This reaction which is a kind of methylation needs reagents NaOH, Bu4NHSO4 and solvent toluene, H2O at temperature of 20 °C. The yield is 100%.

When you are using this chemical, please be cautious about it as the following:
It is very toxic by inhalation, in contact with skin and if swallowed. And it has danger of cumulative effects. Wha's more, this chemical is also toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure.
1. SMILES:Clc1cc([N+]([O-])=O)c(N)cc1
2. InChI:InChI=1/C6H5ClN2O2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H,8H2 
3. InChIKey:PBGKNXWGYQPUJK-UHFFFAOYAL

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 3gm/kg (3000mg/kg) BEHAVIORAL: GENERAL ANESTHETIC National Technical Information Service. Vol. OTS0536149,
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   Office of Toxic Substances Report. Vol. OTS,
mouse LD50 intravenous 63mg/kg (63mg/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 139, 1954.
mouse LD50 oral 800mg/kg (800mg/kg)   Office of Toxic Substances Report. Vol. OTS,
rat LD50 intraperitoneal 200mg/kg (200mg/kg)   Office of Toxic Substances Report. Vol. OTS,
rat LD50 oral 400mg/kg (400mg/kg)   Office of Toxic Substances Report. Vol. OTS,

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