619-16-9

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLORO-1,4-DINITROBENZENE is used as a reagent for the synthesis of novel thiazole derivatives, which have potential applications as coxsackie inhibitors. These inhibitors can be employed in the development of new drugs to treat viral infections, particularly those caused by coxsackieviruses.
Used in Chemical Synthesis:
2-CHLORO-1,4-DINITROBENZENE is also used in the synthesis of other isomers, such as 4-chloro-1,2-dinitrobenzene. These isomers can have various applications in different industries, including the production of dyes, pesticides, and other chemical products.

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

Upstream product

• 36164-93-9 chloro-[1,4]benzoquinone dioxime 
• 619-18-1 2,5-dinitroaniline 
• 121-87-9 2-Chloro-4-nitroaniline 
• 329-71-5 2,5-dinitrophenol 
• 825-41-2 3-chloro-4-nitroaniline 
• 7697-37-2 nitric acid 
• 13362-35-1 2-chloro-1,4-benzoquinone-4-oxime 
• 20607-43-6 sodium isopropanethiolate 

Downstream Products

• 4920-79-0 2-chloro-4-nitroanisole 
• 5131-58-8 2,4-diaminonitrobenzene 
• 619-18-1 2,5-dinitroaniline 
• 615-66-7 2-chloro-p-phenylenediamine 
• 56961-16-1 2,4,5-trinitrochlorobenzene 
• 121-87-9 2-Chloro-4-nitroaniline 
• 201413-50-5 N,N'-bis-(2,5-dinitrophenyl)-1,2-diaminoethane 
• 13059-86-4 2,4-dinitro-N-butylaniline 
• 825-41-2 3-chloro-4-nitroaniline 
• 57356-27-1 5-chloro-2,4-dinitroanisole 
• 1210-96-4 1,3-dimethoxy-4,6-dinitrobenzene 
• 1016-90-6 7-nitro-1,2,4-benzotriazin-3-amine 1-oxide 
• 610-31-1 1,2,4-trinitrobenzene 
• 122834-06-4 2-chloro-5,6-dimethyl-1,4-dinitrocyclohexa-1,3-diene 

Relevant academic research and scientific papers

Aromatic radical anions as possible intermediates in the nucleophilic aromatic substitution (SNAr): An EPR study

The reactions among halonitrobenzenes or polynitrobenzenes and alkoxides, thiolates or tertiary amines have provided the evidence that in a SNAr reaction type a single electron transfer from the nucleophile to the aromatic substrate, to generate two radical species within the solvent cage, can take place to some extent. The detection of radical intermediates by EPR spectroscopy, in several SNAr reactions, is reported.

Addition and Redox Processes in the Reaction of Grignard Reagents with 1,4-Dinitrobenzene. Factors affecting Produdct Distribution

1,4-Dinitrobenzene (1) reacts smootly and irreversibly with alkyl-magnesium or -lithium reagents to give at first the nitroarene radical anion (3) (redox product) and 6-alkyl-2-nitro-5-aci-nitrocyclohexa-1,2-diene (4) (addition product).Intermediate (4) undergoes an immediate addition to the nitro function by a second mole of RMgX or RLi to give trans-4,5-dialkyl-3,6-di-aci-nitrocyclohexene (5), which can be converted into the corresponding trans-5,6-dialkyl-1,4-dinitrocyclohexa-1,3-diene (6) by oxidation with sodium hypochlorite or dichlorodicyanobenzoquinone.The addition process is favoured by lower temperatures and weakly polar and highly viscous solvents, while steric hindrance in the magnesium reagent enhances radical anion (3) formation.These findings are interpreted in terms of a single electron-transfer mechanism in which all factors delaying a geminate recombination of the radical pair favour the redox process to the detriment of addition.The almost absolute stereoselectivity of the double alkylation process is attributed to steric control on the direction of attack of RM to the ene-nitro function of (4) exerted by the axial alkyl group.A detailed e. s. r. study of 1,4-dinitrobenzene radical anion is also reported.

Reactions of Nitrophenols with Phosphorus Oxychloride in Dimethylformamide

A rapid and simple method for the replacement of hydroxyl group of nitrophenols and related compounds by chlorine using phosphorus oxychloride in dimethylformamide at ambient temperature is described.