3531-19-9

Basic information

• Product Name: 2-Chloro-4,6-dinitroaniline
• Synonyms: 2-Chloro-4,6-dinitro;(2-Chloro-4,6-dinitrophenyl)amine;2-chloro-4,6-dinitro-Benzenamine;6-chloro-2,4-dinitro-anilin;LABOTEST-BB LT00159757;2-CHLORO-4,6-DINITROANILINE;2,6-DINITRO-4-CHLOROANILINE;2 4-DINITRO-6-CHLOROANILINE
• CAS NO: 3531-19-9
• Molecular Formula: C₆H₄ClN₃O₄
• Molecular Weight: 217.57
• EINECS: 222-564-9
• Product Categories: Intermediates of Dyes and Pigments;Amines;C2 to C6;Nitrogen Compounds
• Mol File: 3531-19-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 157-159 °C(lit.)
• Boiling Point: 280°C (rough estimate)
• Flash Point: 181.4 °C
• Appearance: yellow crystalline powder and/or chunks
• Density: 2.0410 (rough estimate)
• Vapor Pressure: 7.3E-06mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• PKA: -6.83±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-4,6-dinitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4,6-dinitroaniline(3531-19-9)
• EPA Substance Registry System: 2-Chloro-4,6-dinitroaniline(3531-19-9)

Safety Data

• Hazard Codes: Xn,N,T+
• Statements: 20/21/22-36/37/38-51/53-33-26/27/28
• Safety Statements: 26-28-36/37/39-45-61-36/37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: BX9250000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 3531-19-9(Hazardous Substances Data)

Usage

Uses

6-Chloro-2,4-dinitroaniline is a useful aromatic building block, and has aquatic toxicity properties.

General Description

6-chloro-2,4-dinitroaniline exists in three polymorphic forms which can be separated on the basis of their mechanical properties.

InChI:InChI=1/C6H4ClN3O4/c7-4-1-3(9(11)12)2-5(6(4)8)10(13)14/h1-2H,8H2

Synthetic route

2,4-Dinitroanilin (97-02-9) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
Stage #1: 2,4-Dinitroanilin With hydrogenchloride In water at 50 - 70℃; Stage #2: With sodium perchlorate In water at 70℃; for 2h;	98%
Stage #1: 2,4-Dinitroanilin With hydrogenchloride In water at 35℃; for 2h; Stage #2: With chlorine In water at 45℃; Stage #3: With dihydrogen peroxide In water at 60 - 65℃; for 6h; Temperature;	98.4%
With hydrogenchloride; dmap; dihydrogen peroxide In water at 20 - 30℃; for 3h; Reagent/catalyst;	97.2%

2-Chloroaniline (95-51-2) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
With sulfuric acid; nitric acid at 0 - 40℃; for 1h;	56%
Multi-step reaction with 3 steps 1: diethyl ether 2: nitric acid / -15 °C / folgendes bei Raumtemperatur 3: water View Scheme

5-chloro-4-methoxy-1,3-dinitrobenzene (23789-10-8) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
With methanol; ammonia

1,2-dichloro-3,5-dinitrobenzene (2213-80-1) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
With ethanol; ammonia
Multi-step reaction with 2 steps 1: aq. NaN3 2: NH3, NaOAc / ethanol View Scheme

1-chloro-2,3,5-trinitro-benzene (242477-68-5) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
With ethanol; ammonia

N-ethyl-N'-(2-chloro-4,6-dinitro-phenyl)-N-nitro-urea (861366-66-7) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
With water

2-Chloro-4-nitroaniline (121-87-9) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
With sulfuric acid; sulfur trioxide; nitric acid

2-chloro-4,6-dinitrophenyl azide (89598-75-4) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
With ammonia; sodium acetate In ethanol

hydrogenchloride (7647-01-0) + chlorine (7782-50-5) + acetic acid (64-19-7) + 2,4-Dinitroanilin (97-02-9) → 2-chloro-4,6-dinitroaniline (3531-19-9)

hydrogenchloride (7647-01-0) + 2,4-Dinitroanilin (97-02-9) + potassium chlorate → 2-chloro-4,6-dinitroaniline (3531-19-9)

hydrogenchloride (7647-01-0) + 2,4-Dinitroanilin (97-02-9) + sodium hypochlorite → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
at 15 - 20℃;

1,2-dichloro-3,5-dinitrobenzene (2213-80-1) + ammonia (7664-41-7) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
at 105℃; im Rohr;

5-chloro-4-methoxy-1,3-dinitrobenzene (23789-10-8) + methanol. NH3 → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
at 100℃;

1-chloro-2,3,5-trinitro-benzene (242477-68-5) + ammonia (7664-41-7) → 2-chloro-4,6-dinitroaniline (3531-19-9)

ethanol (64-17-5) + N-ethyl-N'-(2-chloro-4,6-dinitro-phenyl)-N-nitro-urea (861366-66-7) + ammonia (7664-41-7) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
at 100℃;

N-ethyl-N'-(2-chloro-4,6-dinitro-phenyl)-N-nitro-urea (861366-66-7) + water (7732-18-5) → ethylnitramine (19091-98-6) + 2-chloro-4,6-dinitroaniline (3531-19-9) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5)

N-ethyl-N'-(2-chloro-phenyl)-urea (62635-53-4) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / -15 °C / folgendes bei Raumtemperatur 2: water View Scheme

2,3-dinitrochlorobenzene (602-02-8) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: oleum; fuming nitric acid / 160 - 170 °C 2: alcohol; ammonia View Scheme

2-chloro-4,6-dinitro-phenol (946-31-6) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
Multi-step reaction with 2 steps 2: alcohol; ammonia View Scheme
Multi-step reaction with 2 steps 1: diethylaniline 2: alcohol; ammonia View Scheme

2,3-dinitroaniline (602-03-9) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitrosylsulfuric acid / Diazotization.man traegt die Diazoniumsalz-Loesung in Kupfer(I)-chlorid-Loesung ein 2: oleum; fuming nitric acid / 160 - 170 °C 3: alcohol; ammonia View Scheme

2,4-dinitroacetanilide (610-53-7) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated sulfuric acid / 110 °C 2: hydrochloric acid; potassium chlorate View Scheme

1,2-dichloro-benzene (95-50-1) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3+H2SO4 2: alcohol; ammonia View Scheme

Acetanilid (103-84-4) → 2-chloro-4,6-dinitroaniline (3531-19-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid / 0 °C 2: concentrated sulfuric acid / 110 °C 3: hydrochloric acid; potassium chlorate View Scheme

pyridine-2-carbonyl chloride (29745-44-6) + 2-chloro-4,6-dinitroaniline (3531-19-9) → C12H7ClN4O5

Conditions	Yield
Stage #1: 2-chloro-4,6-dinitroaniline With sodium hydroxide In water for 0.5h; Stage #2: pyridine-2-carbonyl chloride In water at 5 - 20℃; for 3h;	95%

2-chloro-4,6-dinitroaniline (3531-19-9) + benzoyl chloride (98-88-4) → N-(6-chloro-2,4-dinitrophenyl)benzamide (91692-86-3)

Conditions	Yield
Stage #1: 2-chloro-4,6-dinitroaniline With sodium hydroxide In water for 0.5h; Stage #2: benzoyl chloride In water at 5 - 20℃; for 3h;	91%
With pyridine

2-benzofuroyl chloride (41717-28-6) + 2-chloro-4,6-dinitroaniline (3531-19-9) → N-(6-chloro-2,4-dinitrophenyl)benzofuran-2-carboxamide

Conditions	Yield
Stage #1: 2-chloro-4,6-dinitroaniline With sodium hydroxide In water for 0.5h; Stage #2: 2-benzofuroyl chloride In water at 5 - 20℃; for 3h;	90%

5-nitrofuran-2-carboxylic chloride (25084-14-4) + 2-chloro-4,6-dinitroaniline (3531-19-9) → N-(6-chloro-2,4-dinitrophenyl)-5-nitrofuran-2-carboxamide

Conditions	Yield
Stage #1: 2-chloro-4,6-dinitroaniline With sodium hydroxide In water for 0.5h; Stage #2: 5-nitrofuran-2-carboxylic chloride In water at 5 - 20℃; for 3h;	90%

2-chloro-4,6-dinitroaniline (3531-19-9) + isooxazole-5-carbonyl chloride (62348-13-4) → N-(6-chloro-2,4-dinitrophenyl)isoxazole-5-carboxamide

Conditions	Yield
Stage #1: 2-chloro-4,6-dinitroaniline With sodium hydroxide In water for 0.5h; Stage #2: isooxazole-5-carbonyl chloride In water at 5 - 20℃; for 3h;	87%

2-chloro-4,6-dinitroaniline (3531-19-9) + carbonic acid dimethyl ester (616-38-6) → 4-chloro-1,3-dimethyl-6-nitro-1H-benzo[d]imidazol-2(3H)-one

Conditions	Yield
With copper(II) acetate monohydrate In neat (no solvent) at 100℃; under 7600.51 Torr; for 20h; Autoclave; Inert atmosphere; Green chemistry;	75%

2-chloro-4,6-dinitroaniline (3531-19-9) + 4-nitro-benzoyl chloride (122-04-3) → 2',4',4-trinitro-6'-chlorobenzanilide (141245-77-4)

Conditions	Yield
In nitrobenzene at 190 - 200℃; for 4h;	74%

2-chloro-4,6-dinitroaniline (3531-19-9) + acetic acid (64-19-7) → 4-chloro-2-methyl-1H-benzimidazol-6-amine

Conditions	Yield
Stage #1: 2-chloro-4,6-dinitroaniline; acetic acid With tin(II) chloride dihdyrate for 4h; Reflux; Stage #2: With hydrogenchloride In water for 1h; Reflux;	69%

6-(9-carbazolyl)-3-oxahexane-1,5-diol (938190-38-6) + 2-chloro-4,6-dinitroaniline (3531-19-9) → 6-[3-(2-chloro-4,6-dinitrophenylazo)carbazol-9-yl]-3-oxahexane-1,5-diol

Conditions	Yield
Stage #1: 2-chloro-4,6-dinitroaniline With sulfuric acid; sodium nitrite In water; acetic acid at 15℃; for 1h; Stage #2: 6-(9-carbazolyl)-3-oxahexane-1,5-diol In 2-methyl-propan-1-ol; water for 1h;	36%

formic acid (64-18-6) + 2-chloro-4,6-dinitroaniline (3531-19-9) → 5-amino-4,7-dichlorobenzimidazole (118134-23-9) + 7(4)-chloro-5(6)-formylaminobenzimidazole (118134-22-8)

Conditions	Yield
With hydrogenchloride; tin for 6h; Heating;	A 23.5% B 20%

2-chloro-4,6-dinitroaniline (3531-19-9) → 1-chloro-2-iodo-3,5-dinitrobenzene (100191-51-3)

Conditions	Yield
With sulfuric acid; acetic acid Diazotization.Eintragen des Reaktionsgemisches in gesaettigte wss. KI-Loesung;
Stage #1: 2-chloro-4,6-dinitroaniline With sulfuric acid; acetic acid; sodium nitrite at 70℃; Stage #2: With potassium iodide In water at 50℃; for 0.25h;

2-chloro-4,6-dinitroaniline (3531-19-9) + acetic anhydride (108-24-7) → acetic acid-(2-chloro-4,6-dinitro-anilide) (89894-26-8)

Conditions	Yield
With sulfuric acid; acetic acid
With sulfuric acid

carbon disulfide (75-15-0) + 2-chloro-4,6-dinitroaniline (3531-19-9) + sodium monochloroacetic acid (3926-62-3) → 3-(2-chloro-4,6-dinitro-phenyl)-2-thioxo-thiazolidin-4-one (56205-33-5)

Conditions	Yield
(i) aq. NH3, (ii) /BRN= 3597157/; Multistep reaction;

4-chloro-3,5-dinitrobenzotrifluoride (393-75-9) + 2-chloro-4,6-dinitroaniline (3531-19-9) → 6'-chloro-4-trifluoromethyl-2,2',4',6-tetranitrodiphenylamine (53393-21-8)

Conditions	Yield
In N-methyl-acetamide
With sodium hydride

5-aminonaphthalene-2-sulfonic acid (119-79-9) + 2-chloro-4,6-dinitroaniline (3531-19-9) + 4-Amino-1-hydroxy-N-[4-(2,4-di-tert-pentylphenoxy)butyl]-2-naphthamide → C47H49ClN6O10S (54179-88-3)

Conditions	Yield
Multistep reaction;

1-chloro-2,4-dinitro-6-trifluoromethylbenzene (392-95-0) + 2-chloro-4,6-dinitroaniline (3531-19-9) → (2-Chloro-4,6-dinitro-phenyl)-(2,4-dinitro-6-trifluoromethyl-phenyl)-amine (57729-69-8)

2-chloro-4,6-dinitroaniline (3531-19-9) + 4-Acetylamino-5-hydroxy-naphthalene-2-sulfonic acid + 4-Amino-1-hydroxy-N-[4-(2,4-di-tert-pentylphenoxy)butyl]-2-naphthamide → C49H52ClN7O11S (54180-03-9)

Conditions	Yield
Multistep reaction;

2-chloro-4,6-dinitroaniline (3531-19-9) → 6-chloro-2,4-diaminobenzimidazole (17625-81-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol; formic acid at 20℃; under 2280 Torr; for 23h;

Upstream product

• 89598-75-4 2-chloro-4,6-dinitrophenyl azide 
• 7647-01-0 hydrogenchloride 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 97-02-9 2,4-Dinitroanilin 
• 861366-66-7 N-ethyl-N'-(2-chloro-4,6-dinitro-phenyl)-N-nitro-urea 
• 7732-18-5 water 
• 946-31-6 2-chloro-4,6-dinitro-phenol 
• 95-50-1 1,2-dichloro-benzene 
• 103-84-4 Acetanilid 
• 610-53-7 2,4-dinitroacetanilide 
• 602-03-9 2,3-dinitroaniline 
• 602-02-8 2,3-dinitrochlorobenzene 
• 95-51-2 o-chloroaniline 

Downstream Products

• 56205-33-5 3-(2-chloro-4,6-dinitro-phenyl)-2-thioxo-thiazolidin-4-one 
• 75370-59-1 6-chloro-2,4-dinitrophenyl urea 
• 3618-73-3 2,2'-({5-acetamido-4-[(2-chloro-4,6-dinitrophenyl)azo]-2-methoxyphenyl}imino)diethyl diacetate 
• 1135091-77-8 C₂₃H₂₃ClN₆O₁₁ 
• 79295-99-1 C₁₉H₂₁ClN₆O₆ 
• 85508-41-4 C₂₁H₂₁ClN₆O₆ 
• 540-82-9 ethyl sulfate 
• 875839-09-1 benzoic acid-(2,4-diamino-6-chloro-anilide) 
• 861797-92-4 acetic acid-(2,N-dichloro-4,6-dinitro-anilide) 
• 89581-78-2 2-chloro-4.6-dinitrophenyl hydrazine 

Relevant articles and documents

Synthesis process 6 -chloro -2-4 -dinitroaniline

The invention provides a synthesis process of 6 - chloro -2 and 4 -dinitroaniline, which comprises a pulping step of dissolving 2, 4 -dinitroaniline in an organic solvent. A chlorination step in which a chlorinating agent is added to the slurry obtained in the above slurrying is a chlorination step. and: The post-treatment step after the chlorination is completed. In the pulping step, an acid solution is further added. The chlorinating agent is dichlorohydantoin. The reaction system is stable in reaction system, thorough in material reaction, less in side reaction, high in raw material conversion rate, good in reaction product crystal shape, high in yield, high in production efficiency, remarkable in production efficiency, remarkable in energy saving and emission reduction effect and high in safety and controllability.

Method for synthesizing 6-chloro-2, 4-dinitroaniline by chlorine and hydrogen peroxide method

The invention discloses a method for synthesizing 6-chloro-2, 4-dinitroaniline by a chlorine and hydrogen peroxide method. The method comprises the following steps of grinding 2, 4-dinitroaniline andadding the ground 2, 4-dinitroaniline into a kettle; adding a chlorine and hydrogen peroxide combined chlorination mother liquor into the kettle, raising the temperature to 25-65 DEG C, and stirring for 1-2 hours; introducing chlorine at the temperature of 25-65 DEG C, wherein the molar ratio of the 2, 4-dinitroaniline to the chlorine is 1: (0.51-0.53); keeping the temperature at 30-70 DEG C for 1-2 hours; raising the temperature to 45-80 DEG C, and adding hydrogen peroxide according to a molar ratio of 2, 4-dinitroaniline to the hydrogen peroxide of 1: (0.52-0.8); carrying out heat preservation reaction at 80 +/-5 DEG C for 1-2 hours, and carrying out solid-liquid separation after the reaction is finished to respectively obtain a filter cake and the chlorine and hydrogen peroxide combinedchlorination mother liquor. According to the method, the purity of the obtained product is high, the production efficiency is high, the mother liquor can be continuously recycled, and the zero-emission clean production is realized.

Synthetic method for 2,4-dinitro-6-chloroaniline

The invention discloses a synthetic method for 2,4-dinitro-6-chloroaniline. The method comprises the following steps: dispersing substrate 2,4-dinitroaniline into a mixed solution composed of hydrochloric acid, a catalyst and a dispersing agent, performing pulping, introducing a chlorine gas for a first-stage chlorination reaction, then adding hydrogen peroxide dropwise for a second-stage chlorination reaction, after the reaction is completed, filtering the reaction liquid, washing the filter cake to the pH of 6.0-7.0, and performing drying to obtain the product 2,4-dinitro-6-chloroaniline. According to the method provided by the invention, compounding of the phase transfer catalyst and the dispersing agent is adopted for use, so that a reaction material system has good fluidity, the use amount of chlorinating agents is greatly reduced, and the purity and yield of the product are improved; and after filtration is performed, the hydrochloric acid, catalyst and dispersing agent in the mother liquor can be returned to a reaction to continue being used, the use amount of the two chlorinating agents is controlled, so that the acidity of the mother liquor is kept balanced, a salt component is not contained, the mother liquor can realize an endless cycle mechanical application, clean production is truly achieved, and the energy-saving emission-reducing benefits are remarkable.