6966-45-6

Usage

Uses

Used in Pharmaceutical Industry:
(4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE is used as a synthetic intermediate for the development of various pharmaceuticals. Its reactivity allows for the formation of diverse chemical structures, contributing to the creation of new drug candidates.
Used in Agrochemical Industry:
In the agrochemical sector, (4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE is used as a key component in the synthesis of pesticides and other crop protection agents. Its versatility aids in the development of effective and targeted agrochemicals.
Used in Fine Chemicals Industry:
(4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE is employed as a building block in the synthesis of specialty chemicals, including dyes, fragrances, and other high-value compounds. Its unique properties enable the production of a wide range of fine chemicals with specific applications.
Used in Organic Synthesis:
As a sulfonyl chloride derivative, (4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE is used as a reagent in various organic synthesis processes. Its ability to participate in nucleophilic substitution and other reactions makes it a valuable tool for creating complex organic molecules.
Note: The uses listed are based on the general applications of sulfonyl chloride derivatives in various industries and the compound's description as a building block and reagent in organic synthesis. Specific uses may vary depending on the industry and the particular chemical properties of (4-CHLORO-PHENYL)-METHANESULFONYL CHLORIDE.

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

• 544-47-8 S-(4-chlorobenzyl)isothiourea hydrochloride 
• 92988-97-1 S-(4-chlorobenzyl)methylthiocarbamate 
• 624731-62-0 S-(4-chlorobenzyl) ethanethioate 
• 622-95-7 4-chlorobenzyl bromide 
• 6317-27-7 p-chlorophenyl mesylate 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 23566-17-8 bis(4-chlorobenzyl)disulfide 

Downstream Products

• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 111908-04-4 C-(4-Chloro-phenyl)-N-(4-phenyl-butyl)-methanesulfonamide 
• 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 
• 85952-22-3 N-tert-Butyl-C-(4-chloro-phenyl)-methanesulfonamide 
• 831-81-2 4-chlorophenyl(phenyl)methane 
• 30203-87-3 1-chloro-4-(4-methylbenzyl)benzene 
• 91410-28-5 1-chloro-4-(3-methylbenzyl)benzene 
• 55676-88-5 1-chloro-4-(2-methylbenzyl)benzene 
• 85650-22-2 (4-Chloro-phenyl)-methanesulfonic acid 2-chloro-ethyl ester 
• 109103-02-8 (4-chloro-phenyl)-methanethiosulfonic acid S-benzyl ester 

Relevant academic research and scientific papers

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.

Alkyne Linchpin Strategy for Drug:Pharmacophore Conjugation: Experimental and Computational Realization of a Meta-Selective Inverse Sonogashira Coupling

The late-stage functionalization (LSF) of pharmaceutical and agrochemical compounds by the site-selective activation of C-H bonds provides access to diverse structural analogs and expands synthetically-accessible chemical space. We report a C-H functionalization LSF strategy that hinges on the use of an alkyne linchpin to assemble conjugates of sp2-rich marketed pharmaceuticals and agrochemicals with sp3-rich 3D fragments and natural products. This is accomplished through a template-assisted inverse Sonogashira reaction that displays high levels of selectivity for the meta position. This protocol is also amenable to distal structural modifications of α-amino acids. The transformation of alkyne functionality to other functional groups further highlights the applicative potential. Computational and experimental mechanistic studies shed light on the detailed mechanism. Turnover-limiting 1,2-migratory insertion of the bromoalkyne coupling partner occurs after relatively fast C-H activation. While this insertion occurs unselectively, regioconvergence results from one of the adducts undergoing a 1,2-trialkylsilyl migration to form the alkynylated product. A heterobimetallic Pd-Ag transition structure is essential for product formation in the β-bromide elimination step.

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.

Design, Sustainable Synthesis, and Programmed Reactions of Templated N-Heteroaryl-Fused Vinyl Sultams

A de novo design and synthesis of N-heteroaryl-fused vinyl sultams as templates for programming chemical reactions on vinyl sultam periphery or (hetero)aryl ring is described. The key features include rational designing and sustainable synthesis of the template, customized reactions of vinyl sultams at C=C bond or involving N-S bond cleavage, and reactions on the periphery of the heteroaryl ring for late-stage diversification. The simple, easy access to the template coupled with opportunities for the synthesis of diversely functionalized heterocyles from a single template constitutes a rare study in contemporary organic synthesis.

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.

Tert -Butyl Hypochlorite Mediated Oxidative Chlorination of S -Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides

Under neutral conditions, a variety of S-alkylisothiourea salts were smoothly converted into the corresponding sulfonyl chlorides through tert-butyl chlorite mediated oxidative chlorination in good to excellent yields after simple purification. In addition to the environmental and procedural advantages of this method, the neutral conditions potentially make it applicable to substrates that bear acid-sensitive functional groups. For example, the Cbz-protected 2-aminoethanesulfonyl chloride could be synthesized in moderate to good yields under the current neutral conditions, and the acid-sensitive Cbz-protecting group was not affected.

Clean and economic synthesis of alkanesulfonyl chlorides from S-alkyl isothiourea salts via bleach oxidative chlorosulfonation

A simple procedure for clean and economic synthesis of alkanesulfonyl chlorides via bleach-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is disclosed. This procedure is environment- and worker-friendly with the advantages of readily accessible materials and reagents, simple and safe operations, easy purification without chromatography, and affords high yields of up to 99%.

Convenient and environment-friendly synthesis of sulfonyl chlorides from S -alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation

A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from 'waste water' can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable. Georg Thieme Verlag Stuttgart, New York.

Simple synthesis of sulfonyl chlorides from thiol precursors and derivatives by NaClO2-mediated oxidative chlorosulfonation

A simple method to synthesize diverse sulfonyl chlorides through NaClO 2-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is presented. The approach features safe operation, environmental friendliness, convenient purification procedures, and delivers high yields of up to 96%. The procedure is also applicable to substrates such as thiols, disulfides, thioacetates, and xanthates. It is a versatile and convenient method for the synthesis of various sulfonyl chlorides from different thiol precursors and derivatives. Georg Thieme Verlag Stuttgart, New York.