606-21-3

Basic information

• Product Name: 2-Chloro-1,3-dinitrobenzene
• Synonyms: 1-CHLORO-2,6-DINITROBENZENE;2,6-DINITROCHLOROBENZENE;2-CHLORO-1,3-DINITROBENZENE;1,3-Dinitro-2-chlorobenzene;2-chloro-1,3-dinitro-benzen;2-Chloro-1,3-dintrobenzene;Benzene, 2-chloro-1,3-dinitro-;1-Chloro-2,6-dinitrobenzene~2,6-Dinitrochlorobenzene
• CAS NO: 606-21-3
• Molecular Formula: C₆H₃ClN₂O₄
• Molecular Weight: 202.55
• EINECS: 210-107-6
• Product Categories: Intermediates of Dyes and Pigments;Alcohols and Derivatives
• Mol File: 606-21-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 86-88°C
• Boiling Point: 315°C
• Flash Point: 315°C
• Appearance: orange yellow aciform crystal
• Density: 1,687 g/cm3
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.5870 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in alcohol. Moderately soluble in benzene, ether. Practically insoluble in water.
• Merck: 14,2137
• BRN: 522187
• CAS DataBase Reference: 2-Chloro-1,3-dinitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-1,3-dinitrobenzene(606-21-3)
• EPA Substance Registry System: 2-Chloro-1,3-dinitrobenzene(606-21-3)

Safety Data

• Statements: 23/24/25-33-50/53
• Safety Statements: 28-36/37-45-60-61
• RIDADR: 3441
• RTECS: CZ0525500
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 606-21-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow crystals. Soluble in ethanol, ether, and toluene

Uses

Different sources of media describe the Uses of 606-21-3 differently. You can refer to the following data:
1. The commercial mixture of chlorodinitrobenzenes is used to synthesize other compounds.
2. 2-Chloro-1,3-dinitrobenzene can be used as intermediates of dyes and pigments. Also used as solvents in HPLC, NMR.
3. 2,6-Dinitrochlorobenzene (2-Chloro-1,3-dinitrobenzene) is a thiol-modifying agent.

Hazard

Toxic if swallowed. Toxic in contact with skin. Fatal if inhaled. May cause damage to organs through prolonged or repeated exposure. Very toxic to aquatic life with long lasting effects.

Synthesis

The synthesis of?2-Chloro-1,3-dinitrobenzene is as follows:Add 800ml of sulfolane as solvent to a 2L flask, then add 246.5g of 3,5-dinitro-4-chlorobenzoic acid and 168g of sodium bicarbonate,Heat to 195°C to react for 2h. After the reaction is complete, cool to 130°C and distill under reduced pressure.The product 2-Chloro-1,3-dinitrobenzene, 178.4g, was obtained by rectification with a yield of 88.1%.

InChI:InChI=1/C6H3ClN2O4/c7-6-4(8(10)11)2-1-3-5(6)9(12)13/h1-3H

Upstream product

• 118-97-8 4-chloro-3,5-dinitrobenzoic acid 
• 108-90-7 chlorobenzene 
• 7647-01-0 hydrogenchloride 
• 606-22-4 2,6-dinitroaniline 
• 64-19-7 acetic acid 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 88-73-3 2-Chloronitrobenzene 
• 573-56-8 2,6-dinitrophenol 
• 98-59-9 p-toluenesulfonyl chloride 
• 91-66-7 N,N-diethylaniline 

Downstream Products

• 6526-53-0 1-(2,6-dinitro-phenyl)-pyridinium; chloride 
• 853918-27-1 (2,6-dinitro-phenyl)-[2]pyridyl-amine 
• 3535-67-9 2,6-dinitroanisole 
• 13278-85-8 Ethyl-N-(2,6-dinitro-phenoxy)-carbamat 
• 38100-27-5 t-Butyl-N-(2,6-dinitrophenoxy)-carbamat 
• 62902-21-0 (2,6-Dinitro-phenyl)-(3,4,5-tris-trifluoromethyl-phenyl)-amine 
• 68200-48-6 Dimethyl-thiocarbamic acid S-[2-(2-dimethylcarbamoylsulfanyl-3-nitro-phenyldisulfanyl)-6-nitro-phenyl] ester 
• 35213-00-4 2,6-dinitrobenzonitrile 
• 3396-31-4 morpholine-4-carbodithioic acid 2,6-dinitro-phenyl ester 
• 16242-36-7 N-(β-Dimethylamino-ethyl)-2,6-dinitroanilin 
• 56224-09-0 N-(2-Diethylamino-ethyl)-2,6-dinitro-anilin 
• 56042-38-7 N-methyl-2,6-dinitrodiphenylamine 
• 56224-08-9 N-Propionyl-2.6-dinitroanilin 
• 573-55-7 2-fluoro-1,3-dinitrobenzene 

Relevant articles and documents

Preparation method of 4-amino-1, 3-dihydro-benzimidazole-2-one

The invention provides a preparation method of 4-amino-1, 3-dihydro-benzimidazole-2-one, which comprises the following steps: Q1, preparation of 2, 6-dinitrochlorobenzene, Q2, preparation of 2, 6-dinitroaniline, Q3, preparation of 3-nitro-o-phenylenediamine, Q4, preparation of 4-nitro-1H-benzo[d]imidazole-2(3H)-one and Q5, preparation of 4-amino-1, 3-dihydro-benzimidazole-2-one. According to the preparation method, 3, 5-dinitro-4-chlorobenzoic acid which is low in price is used as a raw material, and the high-yield 4-amino-1, 3-dihydro-benzimidazole-2-one is obtained through reactions such asdecarboxylation and ammoniation. The whole reaction process is easy to control, the product yield is high, good social benefits and economic benefits can be brought, and the economic value potential is large.

Unusual behaviour during the route of a Japp-Klingemann reaction

Performing a standard Japp-Klingemann synthesis that involved diazotation of 2,6-dinitroaniline and reaction with pentane-2,4-dione in aqueous hydrochloric acid medium surprisingly yielded a mixture of the expected 2,6-dinitro-and the unexpected 2-chloro-6-nitro-substituted hydrazones. This mixture was isolated as solid-solution crystals containing the components in an approximate ratio of 1 to 2. Based on both, selected compounds of comparison that show the aromatic ring substituents changed in position and intermediate diazonium salts, potential causal connections of the unusual behaviour during the route of the particular Japp-Klingemann reaction were studied. X-Ray crystal structures of the relevant compounds have been determined to support the discussion.

Synthesis of 2-N-alkyl(aryl)amino-7-nitrobenzothiazoles

A highly efficient synthesis of 2-N-alkyl(aryl)amino-7-nitrobenzothiazoles has been developed. The key step involves intramolecular cyclization of a thiourea facilitated by the nitro group. A highly efficient synthesis of 2-N-alkyl(aryl)amino-7-nitrobenzothiazoles has been developed. The key step involves intramolecular cyclization of a thiourea facilitated by the nitro group.