6966-45-6

Basic information

• Product Name: (4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE
• Synonyms: 4-CHLOROBENZYLSULFONYL CHLORIDE;4-CHLOROBENZENEMETHANESULFONYL CHLORIDE;(4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE;[(4-CHLOROPHENYL)METHYL]SULPHONYL CHLORIDE;[(4-CHLOROPHENYL)METHYL]SULFONYL CHLORIDE;P-CHLORO-ALPHA-TOLUENESULFONYL CHLORIDE;4-Chloro-alpha-toluenesulfonyl chloride;(4-CHLOROPHENYL)METHANESULPHONYLCHLORIDE
• CAS NO: 6966-45-6
• Molecular Formula: C₇H₆Cl₂O₂S
• Molecular Weight: 225.09
• Product Categories: Phenyls & Phenyl-Het;Sulphonyl Chlorides;Benzenesulfonyl chloride;Sulphonyl Chlorides;Phenyls & Phenyl-Het
• Mol File: 6966-45-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 93-97 °C
• Boiling Point: 321.2 °C at 760 mmHg
• Flash Point: 148 °C
• Appearance: /
• Density: 1.499 g/cm³
• Vapor Pressure: 2.36E-20mmHg at 25°C
• Refractive Index: 1.577
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: (4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE(6966-45-6)
• EPA Substance Registry System: (4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE(6966-45-6)

Safety Data

• Hazard Codes: C,Xi
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 6966-45-6(Hazardous Substances Data)

Usage

General Description

(4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE, also known as 4-chlorobenzenesulfonyl chloride, is an organic compound with the chemical formula C7H6Cl2O2S. It is a sulfonyl chloride derivative that is commonly used as a building block in organic synthesis. The compound is a reactive and versatile reagent, often used in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. It is a colorless to pale yellow liquid with a strong, irritating odor, and it is corrosive to metals and tissue. (4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE is also classified as a hazardous chemical and should be handled and stored with care.

InChI:InChI=1/C22H27N3O6/c1-13-6-7-16(14(2)10-13)23-19(26)8-9-20(27)24-25-22(28)15-11-17(29-3)21(31-5)18(12-15)30-4/h6-7,10-12H,8-9H2,1-5H3,(H,23,26)(H,24,27)(H,25,28)

Upstream product

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• 23566-17-8 bis(4-chlorobenzyl)disulfide 
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• 104-83-6 1-Chloro-4-(chloromethyl)benzene 

Downstream Products

• 111874-95-4 C-(4-Chloro-phenyl)-N-(3-phenyl-propyl)-methanesulfonamide 
• 2510-74-9 (E)-1,2-di(4-chlorophenyl)ethene 
• 2510-74-9 cis-4,4'-dichlorostilbene 
• 71799-35-4 (4-chlorophenyl)methanesulfonamide 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 152271-20-0 N-(1-acetylcyclohexyl)-4-chlorophenyl-methanesulfonamide 
• 416856-09-2 C-(4-Chloro-phenyl)-N-(1,1-dimethyl-prop-2-ynyl)-methanesulfonamide 
• 416856-18-3 methyl 1-(4-chlorophenylmethanesulfonylamino)-1-cyclopentanecarboxylate 
• 118980-03-3 6β-{[(4-chloro-phenyl)-methanesulfonyl]-amino}-penicillanic acid benzyl ester 
• 115187-96-7 2-(carboxy-{[(4-chloro-phenyl)-methanesulfonyl]-amino}-methyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid benzyl ester 
• 17075-12-6 <4-Chlor-phenyl>-methansulfonylbromid 

Relevant articles and documents

Design, synthesis and biological evaluation of novel N-sulfonylamidine-based derivatives as c-Met inhibitors via Cu-catalyzed three-component reaction

In our continuing efforts to develop novel c-Met inhibitors as potential anticancer candidates, a series of new N-sulfonylamidine derivatives were designed, synthesized via Cu-catalyzed multicomponent reaction (MCR) as the key step, and evaluated for their in vitro biological activities against c-Met kinase and four cancer cell lines (A549, HT-29, MKN-45 and MDA-MB-231). Most of the target compounds showed moderate to significant potency at both the enzyme-based and cell-based assay and possessed selectivity for A549 and HT-29 cancer cell lines. The preliminary SAR studies demonstrated that compound 26af (c-Met IC50 = 2.89 nM) was the most promising compound compared with the positive foretinib, which exhibited the remarkable antiproliferative activities, with IC50 values ranging from 0.28 to 0.72 μM. Mechanistic studies of 26af showed the anticancer activity was closely related to the blocking phosphorylation of c-Met, leading to cell cycle arresting at G2/M phase and apoptosis of A549 cells by a concentration-dependent manner. The promising compound 26af was further identified as a relatively selective inhibitor of c-Met kinase, which also possessed an acceptable safety profile and favorable pharmacokinetic properties in BALB/c mouse. The favorable drug-likeness of 26af suggested that N-sulfonylamidines may be used as a promising scaffold for antitumor drug development. Additionally, the docking study and molecular dynamics simulations of 26af revealed a common mode of interaction with the binding site of c-Met. These positive results indicated that compound 26af is a potential anti-cancer candidate for clinical trials, and deserves further development as a selective c-Met inhibitor.

Optimization of P2Y12 Antagonist Ethyl 6-(4-((Benzylsulfonyl)carbamoyl)piperidin-1-yl)-5-cyano-2-methylnicotinate (AZD1283) Led to the Discovery of an Oral Antiplatelet Agent with Improved Druglike Properties

P2Y12 antagonists are widely used as antiplatelet agents for the prevention and treatment of arterial thrombosis. Based on the scaffold of a known P2Y12 antagonist AZD1283, a series of novel bicyclic pyridine derivatives were designed and synthesized. The cyclization of the ester substituent on the pyridine ring to the ortho-methyl group led to lactone analogues of AZD1283 that showed significantly enhanced metabolic stability in subsequent structure-pharmacokinetic relationship studies. The metabolic stability was further enhanced by adding a 4-methyl substituent to the piperidinyl moiety. Compound 58l displayed potent inhibition of platelet aggregation in vitro as well as antithrombotic efficacy in a rat ferric chloride model. Moreover, 58l showed a safety profile that was superior to what was observed for clopidogrel in a rat tail-bleeding model. These results support the further evaluation of compound 58l as a promising drug candidate.

Photocatalytic Radical Alkylation of Electrophilic Olefins by Benzylic and Alkylic Zinc-Sulfinates

Alkyl radicals are obtained by photocatalytic oxidation of readily prepared or commercially available zinc sulfinates. The convenient benzylation and alkylation of a variety of electron-poor olefins triggered by the iridium(III) complex 6 Ir[dF(CF3)ppy]2(dtbbpy)PF6 as photocatalyst is described. Moreover, it is shown that zinc sulfinates can be used for facile nonradical sulfonylation reactions with highly electrophilic Michael acceptors.