100421-52-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Thiophenecarboxylic acid, 3-fluoro-, methyl ester (9CI) is used as a key intermediate in the synthesis of five-membered heterocyclic compounds, specifically as STING agonists. These STING agonists play a crucial role in modulating the immune response and have potential applications in the development of novel therapeutics for various diseases, including cancer and infectious diseases.
In the preparation of five-membered heterocyclic compounds, 2-Thiophenecarboxylic acid, 3-fluoro-, methyl ester (9CI) serves as a valuable building block due to its unique structural features. The presence of the fluorine atom and the methyl ester group allows for further functionalization and modification, enabling the synthesis of a wide range of biologically active compounds with diverse properties and applications.

InChI:InChI=1/C6H5FO2S/c1-9-6(8)5-4(7)2-3-10-5/h2-3H,1H3

Upstream product

• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 32431-84-8 3-fluoro-2-thiophenecarboxylic acid 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 

Downstream Products

• 32431-84-8 3-fluoro-2-thiophenecarboxylic acid 
• 258522-49-5 3-fluorothiophene-2-carboxylic hydrazide 
• 1820885-11-7 methyl 5-bromo-3-fluorothiophene-2-carboxylate 
• 395664-58-1 4,5-dibromo-3-fluoro-thiophene-2-carboxylic acid methyl ester 
• 395664-56-9 methyl 4-bromo-3-fluorothiophene-2-carboxylate 
• 395664-68-3 4-(4-dodecyloxy-phenyl)-3-fluoro-thiophene-2-carboxylic acid methyl ester 
• 395664-66-1 4-bromo-5-(4-dodecyloxy-phenyl)-3-fluoro-thiophene-2-carboxylic acid methyl ester 
• 614729-70-3 (3-fluorothiophen-2-yl)methanol 

Relevant academic research and scientific papers

A facile and improved synthesis of 3-fluorothiophene

A new efficient and convenient route to 3-fluorothiophene in four steps and 49% overall yield is reported. The fluorine atom was successfully introduced into the thiophene ring in 67% yield using the Schiemann reaction on 2-methoxycarbonylthiophene-3-diazonium tetrafluoroborate. The product, methyl 3-fluorothiophene-2-carboxylate was saponified and the 3-fluorothiophene-2- carboxylic acid was decarboxylated to afford 3-fluorothiophene in 93% yield. Georg Thieme Verlag Stuttgart.

Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones

A practical method for radiofluorination of anilines with [18F]fluoride via N-arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18F-labeling to prepare [

FACTOR XIa INHIBITORS

The present invention provides a compound of Formula (I); and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes. The compounds are selective Factor XIa inhibitors or dual inhibitors of Factor XIa and plasma kallikrein.

3-OXO-TETRAHYDRO-FURO[3,2-B]PYRROL-4(5H)-YL) DERIVATIVES I

The invention relates to amidic oxotetrahydro-2H-furo[3.2-b]pyrrol-4(5H)-yl) derivatives as dual CatS/K inhibitors, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

Ring fluorinated thiophenes: Applications to liquid crystal synthesis

Ring fluorinated thiophenes were synthesized via a Balz-Schiemann fluorination approach and were successfully employed in the synthesis of liquid crystals using regioselective electrophilic bromination and regioselective Suzuki coupling chemistry.

Attempted syntheses of aminofluorothiophenes

It appeared that a key intermediate for 2-amino-3-fluorothiophene (1), methyl 3-fluorothiophene-2-carboxylate (5), had been prepared by a Schiemann reaction of the 3-diazonium salt (6) in xylenes. This report was not correct. Gomberg coupling products 7 with o-xylene are actually formed. We were able to prepare 5 by using special conditions for the Schiemann reaction. The hydrazide derivative of 5 failed to give 1 under Curtius reaction conditions. Two new acetamidofluorothiophene compounds were prepared using Selectfluor(TM) as the fluorinating agent, but no aminofluorothiophenes 1-3 or salts could be obtained by acidic hydrolysis of either amide.

THE BEHAVIOUR OF VICINAL ALKYL AMINOTHIOPHENECARBOXYLATES IN THE SANDMEYER AND SCHIEMANN REACTIONS

The diazotization of vicinal alkyl aminothiophenecarboxylates has been studied. 3-Amino compounds gave clear diazonium salts which yielded the expected halo derivatives in the Sandmeyer and Schiemann conditions.However, 2-amino compounds yielded self-coupling products.