5943-04-4

Basic information

• Product Name: 1-chloro-4-[(chloromethyl)sulphonyl]benzene
• Synonyms: 1-chloro-4-[(chloromethyl)sulphonyl]benzene;(chloromethyl)(4-chlorophenyl)dioxo-lambda~6~-sulfane;1-chloro-4-chloromethanesulfonylbenzene
• CAS NO: 5943-04-4
• Molecular Formula: C₇H₆Cl₂O₂S
• Molecular Weight: 225.09234
• EINECS: 227-701-6
• Mol File: 5943-04-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 364°C at 760 mmHg
• Flash Point: 174°C
• Appearance: /
• Density: 1.456g/cm³
• Vapor Pressure: 3.62E-05mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: 1-chloro-4-[(chloromethyl)sulphonyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chloro-4-[(chloromethyl)sulphonyl]benzene(5943-04-4)
• EPA Substance Registry System: 1-chloro-4-[(chloromethyl)sulphonyl]benzene(5943-04-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5943-04-4(Hazardous Substances Data)

Usage

General Description

1-Chloro-4-[(chloromethyl)sulphonyl]benzene is a chemical compound with the molecular formula C7H6Cl2O2S. It is a white crystalline powder that is primarily used as an intermediate in the synthesis of other organic compounds. The chemical is classified as a chloromethyl sulfonyl halide and is commonly used in the production of pharmaceuticals and agrochemicals. Its unique structure and properties make it a versatile building block for the synthesis of various compounds, and it is widely used in chemical research and development. However, due to its potential toxicity and health hazards, proper safety precautions and handling procedures should be followed when working with this chemical.

InChI:InChI=1/C7H6Cl2O2S/c8-5-12(10,11)7-3-1-6(9)2-4-7/h1-4H,5H2

Upstream product

• 79-43-6 dichloro-acetic acid 
• 100-03-8 4-chlorobenzenesulfinic acid 
• 74-97-5 chlorobromomethane 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 123-09-1 4-chlorophenyl methyl sulfide 
• 108-90-7 chlorobenzene 
• 2156-56-1 sodium dichloroacetate 
• 21506-06-9 acetic acid-(4-chloromethanesulfonyl-anilide) 
• 710-24-7 4-acetamidobenzenesulfinic acid 
• 106-54-7 p-Chlorothiophenol 
• 744221-72-5 (4-chloro-phenylsulfanyl)-methanesulfonic acid 
• 1538-97-2 4-chlorobenzenesulfonyl diazomethane 
• 7569-24-6 4-chloromethanesulfonyl-aniline 
• 7205-90-5 chloromethyl 4-chlorophenyl sulfide 

Downstream Products

• 61496-56-8 2-nitro-4-chloromethylsulfonylaniline 
• 339101-92-7 4-chlorophenyl 5-cyano-2-nitrobenzyl sulfone 
• 1144525-75-6 5-bromo-2-nitrobenzyl 4-chlorophenyl sulfone 
• 1144525-73-4 4-chlorophenyl 5-fluoro-2-nitrobenzyl sulfone 
• 1144525-80-3 3-chloro-2-nitrobenzyl 4-chlorophenyl sulfone 
• 1144525-81-4 3-chloro-4-nitrobenzyl 4-chlorophenyl sulfone 
• 1144525-74-5 5-chloro-2-nitrobenzyl 4-chlorophenyl sulfone 
• 100398-52-5 1-chloro-4-((4-nitrobenzyl)sulfonyl)benzene 
• 1144525-88-1 2-carbomethoxy-4-nitrobenzyl 4-chlorophenyl sulfone 
• 141693-31-4 4-methoxycarbonyl-2-nitrobenzyl 4-chlorophenyl sulfone 
• 1144525-70-1 4-chlorophenyl 2-nitro-5-tert-butylbenzyl sulfone 
• 1144525-87-0 2-chloro-4-nitrobenzyl 4-chlorophenyl sulfone 
• 1144525-72-3 5-carboisopropoxy-2-nitrobenzyl 4-chlorophenyl sulfone 
• 1144525-71-2 4-chlorophenyl 5-methoxy-2-nitrobenzyl sulfone 

Relevant articles and documents

2,4-Disubstituted 5-Nitroimidazoles Potent against Clostridium difficile

Metronidazole is one of the first-line treatments for non-severe Clostridium difficile infections (CDI). However, resistance limits its use in cases of severe and complicated CDI. Structure–activity relationships previously described for the 5-nitroimidazole series have shown that functionalization at the 2- and 4-positions can impart better activity against parasites and anaerobic bacteria than metronidazole. Herein we report the synthesis of new 2,4-disubstituted 5-nitroimidazole compounds that show potent antibacterial activity against C. difficile. We used a vicarious nucleophilic substitution of hydrogen (VNS) reaction to introduce a phenylmethylsulfone at the 4-position and a unimolecular radical nucleophilic substitution (SRN1) reaction to introduce an ethylenic function at the 2-position of the 5-nitroimidazole scaffold.

New synthetic sulfone derivatives inhibit growth, adhesion and the leucine arylamidase APE2 gene expression of Candida albicans in vitro

The successful preventing and effective treatment of invasive Candida albicans infections required research focused on synthesis of new classes of agents and antifungal activity studies. Bromodichloromethyl-4-chloro-3-nitrophenyl sulfone (named compound 6); dichloromethyl-4-chloro-3-nitrophenyl sulfone (named 7); and chlorodibromomethyl-4-hydrazino-3-nitrophenyl sulfone (named 11) on inhibition of planktonic cells' growth, leucine arylamidase APE2 gene expression, and adhesion to epithelial cells were investigated. In vitro anti-Candida activities were determined against wild-types, and the morphogenesis mutants: Δefg1 and Δcph1. MICs of compounds 6, 7 and 11 (concentrated at 0.25-16 μg/ml) were determined using the Clinical and Laboratory Standards Institute Broth Microdilution Method (M27-A3 Document). APE2 expression was analyzed using RT-PCR; relative quantification was normalized against ACT1 in cells growth in YEPD and on Caco-2 cell line. Adherence assay of C. albicans to Caco-2 was performed in 24-well-plate. The structure activity relationship suggested that sulfone containing hydrazine function at C-1 (compound 11) showed higher antifungal activity (cell inhibition% = 100 at 1-16 μg/ml) than the remaining sulfones with chlorine at C-1. Δcph1/Δefg1 was highly sensitive to compound 11, while the sensitivity was reduced in Δcph1/Δefg1::EFG1 (% = 100 at 16-fold higher concentration). Compound 11 significantly affected adherence to epithelium (P ≤0.05) and hyphae formation. The APE2 up-regulation plays role in sulfones' resistance on MAP kinase pathway. Either CPH1 or EFG1 play a role in the resistance mechanism in sulfones. The strain-dependent phenomenon is a factor in the sulfone resistance mechanism. Sulfones' mode of action was attributed to reduced virulence arsenal in terms of adhesiveness and pathogenic potential related to the APE2 expression and morphogenesis.

Evaluation of electrophilic activities of substituted nitroarenes in the VNS reaction with secondary and tertiary carbanions

Relative electrophilic activities of substituted nitroarenes in the vicarious nucleophilic substitution (VNS) reaction with carbanion of chloromethylp-chlorophenyl and bromomethyl phenyl sulfones, 1 and 2, were determined via competitive experiments. The results are in good agreement with relative activities determined earlier in the competitive experiments with carbanion of chloromethyl phenyl sulfone 3 confirming reliability of these data. On the other hand, analogous competitive experiments with tertiary carbanions of chloroform and 1-chloroethyl phenyl sulfone gave results much affected by steric effects thus the VNS reaction with these carbanions cannot be used for evaluation of electrophilic activities of nitroarenes.