59337-92-7

Usage

Uses

Used in Chemical Synthesis:
Methyl 3-chlorosulfonylthiophene-2-carboxylate is used as a sulfonylating reagent for the synthesis of various organic compounds. Its application is crucial in the production of pharmaceuticals, agrochemicals, and other specialty chemicals due to its ability to introduce sulfonyl groups into target molecules, enhancing their reactivity and functional properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 3-chlorosulfonylthiophene-2-carboxylate is used as a key intermediate in the development of novel drug candidates. Its sulfonylating properties allow for the creation of new molecular structures with potential therapeutic applications, contributing to the advancement of drug discovery and development.
Used in Agrochemical Industry:
Methyl 3-chlorosulfonylthiophene-2-carboxylate is also utilized in the agrochemical industry for the synthesis of various pesticides and other crop protection agents. Its role in introducing sulfonyl groups into chemical structures can lead to the development of more effective and targeted agrochemicals, ultimately benefiting agricultural productivity and crop protection.
Used in Specialty Chemicals:
In the specialty chemicals sector, Methyl 3-chlorosulfonylthiophene-2-carboxylate is employed as a versatile building block for the synthesis of a wide range of compounds with specific applications. Its sulfonylating capabilities enable the creation of new materials with tailored properties, such as improved stability, reactivity, or selectivity, which can be applied in various industrial processes and technologies.

InChI:InChI=1/C6H5ClO4S2/c1-11-6(8)5-4(2-3-12-5)13(7,9)10/h2-3H,1H3

Upstream product

• 67-56-1 methanol 
• 59337-91-6 3-chlorosulfonyl-thiophene-2-carboxylic acid chloride 
• 59337-89-2 3-chlorothiophene-2-carboxylic acid 
• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 

Downstream Products

• 140947-38-2 methyl 3-(N-phenyl-N-methyl)sulfamoylthiophene-2-carboxylate 
• 184644-72-2 3-{[(4-chloro-3-methyl-5-isoxazolyl)amino]sulfonyl}-2-thiophenecarboxylic acid methyl ester 
• 373359-62-7 3-[4-(4-oxopiperidin-1-yl)phenylsulfamoyl]thiophene-2-carboxylic acid methyl ester 
• 850635-49-3 3-(3-carboxyphenylsulfamoyl)thiophene-2-carboxylic acid methyl ester 
• 864961-69-3 3-{[2-(4-Fluorophenyl)-2-hydroxy-ethyl]-methyl-sulfamoyl}-thiophene-2-carboxylic acid methyl ester 
• 321713-01-3 3-[2-(4-Fluorophenyl)-ethylsulfamoyl]-thiophene-2-carboxylic acid methyl ester 
• 126910-68-7 methyl 5-chloro-3-(chlorosulfonyl)-thiophene-2-carboxylate 
• 749268-58-4 3-phenylsulfamoylthiophene-2-carboxylic acid methyl ester 
• 1207974-37-5 3-(4-tert-butoxycarbonylamino-benzenesulfonyl)thiophene-2-carboxylic acid methyl ester 
• 1094736-82-9 C₁₃H₁₃NO₄S₂ 
• 321705-76-4 C₁₄H₁₅NO₄S₂ 
• 1096976-86-1 C₁₂H₁₀ClNO₄S₂ 

Relevant academic research and scientific papers

Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts

We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.

Aromatic Chlorosulfonylation by Photoredox Catalysis

Visible-light photoredox catalysis enables the efficient synthesis of arenesulfonyl chlorides from anilines. The new protocol involves the convenient in situ preparation of arenediazonium salts (from anilines) and the reactive gases SO2and HCl (from aqueous SOCl2). The photocatalytic chlorosulfonylation operates at mild conditions (room temperature, acetonitrile/water) with low catalyst loading. Various functional groups are tolerated (e.g., halides, azides, nitro groups, CF3, SF5, esters, heteroarenes). Theoretical and experimental studies support a photoredox-catalysis mechanism.

2,3-Dihydro-3-oxo-thienoisothiazol-1,1-dioxides and their 3-thioxo compounds

2,3-Dihydro-3-oxo-thieno[2,3-d]isothiazole-1,1-dioxide and 2,3-Dihydro-3-oxo-thieno[3,2-d]isothiazole-1,1-dioxide are synthesized. The latter compound can be prepared from 2-chlorothiophene in five steps. Both substances react with Lawessons reagent to give the 3-thioxo derivatives.

Analogues and Derivatives of Tenoxicam. 1. Synthesis and Antiinflammatory Activity of Analogues with Different Residues on the Ring Nitrogen and the Amide Nitrogen

The synthesis of tenoxicam, 4-hydroxy-2-methyl-N-2-pyridyl-2H-thieno-1,2-thiazine-3-carboxamide 1,1-dioxide (1e), and of the analogues with various residues on the ring nitrogen and the amide nitrogen is described.This new class of "oxicams" has pronounced antiinflammatory and analgesic properties.The very specific structure-activity relationship of isomeric and isosteric groups at the amide nitrogen has been evaluated.The substituent in position 2 also has a great influence on the pharmacological properties.Tenoxicam is presently underrgoing clinical trials.

Manufacture of 3-halosulfonylthiophene-carboxylic acid compounds

3-Halosulfonylthiophene-carboxylic acid compounds are manufactured by reacting 3-ketothiophane-carboxylic acid compounds with sulfonic acid compounds, reacting the end product from the 1st reaction stage with alkali metal polysulfides, reacting the end product from the 2nd stage with a dehydrogenating agent and finally reacting the end product from the 3rd stage with halogen and water. The products are starting compounds for the manufacture of drugs, dyes and crop protection agents and have an anti-inflammatory, analgesic and anti-rheumatic action. In particular, the end products I are starting materials for the manufacture of sweeteners which are non-toxic and free from an after-taste, flavor-improving agents, diabetic aids and feedstuffs, and provide the means of a simple and economical synthesis of thiophene-saccharins.

Thienothiazines

The present invention relates to compounds of the formula STR1 wherein A together with the two carbon atoms to which it is attached forms the group STR2 AND THE BROKEN LINE REPRESENTS THE DOUBLE BOND IN GROUP (A); R1 represents a lower alkyl group; R2 represents the residue of an aromatic heterocyclic ring containing from 1 to 4 hetero atoms, which may be substituted by one or two lower alkyl groups, or a phenyl group which may be substituted by halogen, hydroxy, lower alkyl, trifluoromethyl or lower alkoxy and R3 and R4 each represent a hydrogen atom or a lower alkyl group. Also provided are methods for their preparation. The thienothiazine derivatives provided by this invention have anti-flammatory, analgesic and antirheumatic activity.

Thiophene saccharines

Thiophene analogs of saccharine, i.e., the new compounds 2,3-dihydro-3-oxothieno-[3,4-d]-, -[2,3-d]- and -[3,2-d]-isothiazole-1,1-dioxide, and processes for their manufacture. The new compounds are excellent sweeteners and have no unpleasant taste.