16629-19-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Thiophenesulfonyl chloride is used as an intermediate for the synthesis of various pharmaceuticals, including β-Cell apoptosis suppressor. It plays a crucial role in the development of new drugs that can potentially help in the treatment of diabetes by preventing the death of insulin-producing cells in the pancreas.
Used in Organic Synthesis:
2-Thiophenesulfonyl chloride is used as a key component in the preparation of 2-((trans-2-phenyl cyclopropyl)sulfonyl)thiophene, an organic compound with potential applications in various fields, such as materials science and chemical research.
Used in Chemical Research:
The kinetics of reactions of 2-thiophenesulfonyl chloride with substituted anilines in methanol have been reported, showcasing its importance in understanding the reaction mechanisms and optimizing the synthesis processes. Additionally, the kinetics of solvolysis of 2-thiophenesulfonyl chloride in binary solvent mixtures have been studied, further highlighting its significance in chemical research and development.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 3286, 1974 DOI: 10.1021/jo00936a030

InChI:InChI=1/C4H3ClO2S2/c5-9(6,7)4-2-1-3-8-4/h1-3H

Upstream product

• 188290-36-0 thiophene 
• 3437-95-4 2-Iodothiophene 
• 79-84-5 2-thiophenesulfonic acid 
• 52260-00-1 2-thiophene sulfonyl hydrazine 
• 54663-78-4 tributyl(thien-2-yl)stannane 

Downstream Products

• 111711-68-3 5-ethoxy-1-[(2-thienyl)-sulphonyl]-2-pyrrolidinone 
• 108293-30-7 menthyl 2-thiophenesulfinate 
• 129837-18-9 C₁₁H₉NO₃S₂ 
• 39810-48-5 2-Thienylsulfonyl-p-toluidid 
• 39810-52-1 2-Thienylsulfonyl-p-chloranilid 
• 39810-50-9 2-Thiophen-4'-methoxysulfonanilid 
• 55854-41-6 5-methyl-thiophene-2-sulfonic acid anilide 
• 53442-38-9 Thiophene-2-sulfonic acid (3-nitro-phenyl)-amide 
• 52260-00-1 2-thiophene sulfonyl hydrazine 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 142373-72-6 4-(4-{4-[(S)-2-Methoxycarbonyl-2-(thiophene-2-sulfonylamino)-ethyl]-phenoxy}-butyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 6339-87-3 2-thiophensulfonamide 
• 538-39-6 1,2-di-p-tolylethane 

Relevant academic research and scientific papers

Synthesis and properties of N-(2,2,2-trichloroethyl)-2- thiophenesulfonamides

Chlorination of 2-thiophenesulfonamide gave unstable N,N-dichloro-2- thiophenesulfonamide which was brought into reactions with 1,2-polyhaloethenes. The condensation of 2-thiophenesulfonamide with trichloroacetaldehyde afforded N-(2,2,2-trichloro-1-hydroxyethyl)-2-thiophenesulfonamide which reacted with benzene, toluene, 2-chlorothiophene, and phenol to form the corresponding N-(1-aryl-2,2,2-trichloroethyl)-2-thiophenesulfonamides. Under more severe conditions, the latter were converted into 1,1-diaryl-2,2,2-trichloroethanes. The reaction of N-(2,2,2-trichloro-1-hydroxyethyl)-2-thiophenesulfonamide with substituted arenes, including phenol, was regioselective: only the corresponding para-substituted products were obtained. Hydrolysis of N-[2,2,2-trichloro-1-(4- tolyl)ethyl]-2-thiophenesulfonamide yielded N-(2-thienylsulfonyl)-2-(4-tolyl) glycine.

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

Design, Synthesis, and Biological Evaluation of Novel Allosteric Protein Disulfide Isomerase Inhibitors

Protein disulfide isomerase (PDI) is responsible for nascent protein folding in the endoplasmic reticulum (ER) and is critical for glioblastoma survival. To improve the potency of lead PDI inhibitor BAP2 ((E)-3-(3-(4-hydroxyphenyl)-3-oxoprop-1-en-1-yl)benzonitrile), we designed and synthesized 67 analogues. We determined that PDI inhibition relied on the A ring hydroxyl group of the chalcone scaffold and cLogP increase in the sulfonamide chain improved potency. Docking studies revealed that BAP2 and analogues bind to His256 in the b′ domain of PDI, and mutation of His256 to Ala abolishes BAP2 analogue activity. BAP2 and optimized analogue 59 have modest thiol reactivity; however, we propose that PDI inhibition by BAP2 analogues depends on the b′ domain. Importantly, analogues inhibit glioblastoma cell growth, induce ER stress, increase expression of G2M checkpoint proteins, and reduce expression of DNA repair proteins. Cumulatively, our results support inhibition of PDI as a novel strategy to treat glioblastoma.

AlCl3 mediated unexpected migration of sulfonyl groups: Regioselective synthesis of 7-sulfonyl indoles of potential pharmacological interest

A conceptually new and straightforward introduction of sulfonyl groups at the C-7 position of an indole ring has been achieved via AlCl3 mediated unexpected regioselective sulfonyl group migration for N-alkyl/aryl/heteroarylsulfonyl indoles affording potential inhibitors of Mycobacterium tuberculosis H37Rv chorismate mutase.

An easy microwave-assisted synthesis of sulfonamides directly from sulfonic acids

(Chemical Equation Presented) An easy and handy synthesis of sulfonamides directly from sulfonic acids or its sodium salts is reported. The reaction is performed under microwave irradiation, has shown a good functional group tolerance, and is high yielding.

Acyl sulfonamide anti-proliferatives. Part 2: Activity of heterocyclic sulfonamide derivatives

The anti-proliferative activity of acylated heterocyclic sulfonamides is described in Vascular Endothelial Growth Factor-dependent Human Umbilical Vascular Endothelial Cells (VEGF-HUVEC) and in HCT116 tumor cells in a soft agar diffusion assay.

Bispiperidines as antithrombotic agents

Novel compounds which are inhibitors of the binding of fibrinogen to the Gp IIb/IIIa platelet receptors, and which can be used therepeutically as antithrombotic agents

Tin for Organic Synthesis, 13. A New and Regioselective Method for the Synthesis of Aromatic, Heteroaromatic, and Olefinic Sulfonamides by Electrophilic Destannylation

A mild and effective method for the preparation of aromatic and olefinic sulfonamides is described.The reaction of trialkylaryl- (4a-f), heteroaryl- (4g), and vinylic stannanes (4h) with sulfuryl chloride and secondary amines provides the corresponding sulfonamides in an ipso-specific manner. - Keywords: Electrophilic aromatic substitution ; Electrophilic vinylic substitution ; Trialkylstannanes, application of ; Sulfonamides, synthesis of ; Sulfodestannylation, application of

The Use of N,N-Dimethylformamide-Sulfonyl Chloride Complex for the Preparation of Thiophenesulfonyl Chlorides

A 1:1 N,N-dimethylformamide-SO2Cl2 complex was found to be a useful agent for the one-step preparation of thiophenesulfonyl chlorides.

Process for preparing amides by reaction in presence of molecular sieve

There is provided a process for preparing amides which comprises reacting an amine, or an amide, and an acid halide, or anhydride, in suitable molecular proportions, in an inert organic diluent, in the presence of an effective amount of a molecular sieve, until the reaction is completed, separating the molecular sieve, and recovering the amide from the organic mother liquor.