3284-77-3

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 5094, 1989 DOI: 10.1021/jo00282a025

InChI:InChI=1/C7H5Cl2NO2/c8-7(9)5-3-1-2-4-6(5)10(11)12/h1-4,7H

Upstream product

• 3717-25-7 2-nitrobenzaldehyde oxime 
• 98-87-3 benzylidene dichloride 
• 88-72-2 1-methyl-2-nitrobenzene 
• 95-92-1 oxalic acid diethyl ester 
• 552-89-6 2-nitro-benzaldehyde 
• 75-09-2 dichloromethane 
• 528-29-0 1,2-Dinitrobenzene 
• 18483-88-0 o-(NO₂)C₆H₄CH₂OTHP 
• 62673-13-6 o-Nitrobenzyloxytrimethylsilane 
• 5461-32-5 o-nitrophenylpyruvic acid 
• 612-23-7 2-nitrobenzyl chloride 
• 67-66-3 chloroform 
• 98-95-3 nitrobenzene 

Downstream Products

• 20627-73-0 1-(dimethoxymethyl)-2-nitrobenzene 
• 25407-11-8 1,2-bis(2-nitrophenyl)ethyne 
• 88356-11-0 o-nitrobenzaldehyde diethylacetal 
• 65398-91-6 1-(1-Chloro-2-methyl-2-nitro-propyl)-2-nitro-benzene 
• 61593-10-0 o-nitrotriphenylmethane 
• 7647-01-0 hydrogenchloride 
• 552-89-6 2-nitro-benzaldehyde 
• 42467-40-3 2,2'-dinitrostilbene 

Relevant academic research and scientific papers

One-pot, oxidative and selective conversion of benzylic silyl and tetrahydropyranyl ethers to gem-dichlorides using trichloroisocyanuric acid and triphenylphosphine as an efficient and neutral system

A one-pot and oxidative method is described for the first time for the conversion of benzylic trimethylsilyl (TMS) and tetrahydropyranyl (THP) ethers to gem-dichlorides using trichloroisocyanuric acid (TCCA) and triphenylphosphine (PPh3) in neutral media. Various theses substrates containing electron withdrawing or donating groups can be efficiently converted to their corresponding gem-dichlorides in good to excellent yields. The present method shows a high degree of chemoselectivity, and due to its one-pot nature is in accordance with green chemistry.

Vicarious Nucleophilic Chloromethylation of Nitroaromatics

Nitroaromatics substituted with electron-acceptor or electron-donor groups undergo vicarious nucleophilic substitution with the lithium salt of dichloromethane to provide chloromethyl-substituted nitroaromatics in good to high yields. The methodology represents a new strategy for the synthesis of benzyl chlorides.

TDAE strategy for the synthesis of 2,3-diaryl N-tosylaziridines

We report herein an original and rapid synthesis of 2,3-diaryl N-tosylaziridines by TDAE strategy starting from ortho- or para- nitro(dichloromethyl)benzene derivatives and N-tosylimines. A mixture of cis/trans isomers was isolated from 1-(dichloromethyl)-4- nitrobenzene, whereas only trans-aziridines were obtained from ortho-nitro derivatives.

Facile conversion of aldehydes and ketones to gem-dichlorides using chlorodiphenylphosphine/N-chlorosuccinimide as a new and neutral system

Aldehydes and ketones are easily converted to their corresponding gem-dichlorides using a mixture of chlorodiphenylphosphine and N-chlorosuccinimide (ClPPh2/NCS) in dichloromethane under neutral conditions and at room temperature. Copyright Taylor & Francis Group, LLC.

Dihalomethylation of Nitroarenes via Vicarious Nucleophilic Substitution of Hydrogen with Trihalomethyl Carbanions

Trichloro- and tribromomethyl carbanions generated by deprotonation of haloforms with potassium tert-butoxide in a THF-DMF mixture at ca. -70 deg C react with a variety of carbocyclic and heterocyclic nitroarenes according to the vicarious nucleophilic substitution scheme.The reaction provides an efficient and convenient way for the direct introduction of dihalomethyl substituents ortho and para to the nitro group, which in turn can be hydrolyzed to produce nitroaryl aldehydes.

Process for the preparation of 2-nitrobenzaldehyde

2-Nitrobenzaldehyde, a valuable chemical intermediate, is produced by treating the alkali metal salt of a 2-nitrophenylpyruvic acid with an alkali metal hypochlorite in an aqueous medium to produce the corresponding 2-nitrobenzylidene chloride which, upon hydrolysis, yields the desired aldehyde. The 2-nitrophenylpyruvic acid starting material is advantageously prepared through the reaction of a 2-nitrotoluene and a diester of oxalic acid in the presence of an alkali metal alcoholate and can be used directly in the subsequent hypochlorite reaction without isolation. The process is industrially attractive in terms of the overall yield, the availability of starting materials, and the ease of the manipulative steps involved.

Nitrobenzotrichloride or bromide process

In the hypohalite halogenation in a two phase aqueous/organic solvent medium of a mono- or dichloro- or bromo-methylnitrobenzene to a corresponding trihalomethylnitrobenzene, the improvement wherein the reaction is conducted in the presence of a phase transfer catalyst or where the organic phase is a C4 to C8 alkanol.