31968-33-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Acetyl-3-aminothiophene is used as a fine intermediate for the synthesis of dithienopyridines, which have potential applications in the development of pharmaceutical compounds. These dithienopyridines may exhibit biological activities and properties that can be utilized in the creation of new drugs or drug candidates.
Used in Chemical Synthesis:
2-Acetyl-3-aminothiophene is also used as a building block in the synthesis of other organic compounds and materials. Its unique structure allows it to be a versatile intermediate for the development of various chemical products, including dyes, pigments, and other specialty chemicals.

InChI:InChI=1/C6H7NOS/c1-4(8)6-5(7)2-3-9-6/h2-3H,7H2,1H3

Upstream product

• 57892-89-4 2-acetyl-3-azidothiophene 
• 920-37-6 2-Chloroacrylonitrile 
• 24653-75-6 1-mercaptopropan-2-one 

Downstream Products

• 187334-32-3 N-[(2-acetyl-3-thienyl)]phthalimide 
• 69627-02-7 thieno[3,2-b]pyridin-7(4H)-one 
• 22390-25-6 Thieno<3,2-c>pyridazin 
• 1352450-73-7 (2-acetyl-thiophen-3-ylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester 
• 1352450-04-4 (3R)-3-(2-(2-acetylthiophen-3-ylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane trifluoroacetate 
• 1352450-72-6 2-(2-acetylthiophen-3-ylamino)-2-phenylacetic acid 
• 1189104-11-7 (2-Acetyl-thiophen-3-ylamino)-(4-methoxy-phenyl)-acetic acid 
• 925668-99-1 2-(2-bromo-4,5-dimethoxyphenyl)-1-[3-N-(4-methylbenzenesulfonamido)-2-thienyl]ethanone 
• 925668-98-0 2-(2-bromo-4,5-dimethylphenyl)-1-[3-N-(4-methylbenzenesulfonamido)-2-thienyl]ethanone 
• 925668-97-9 2-(2-bromophenyl)-1-[3-N-(4-methylbenzenesulfonamido)-2-thienyl]ethanone 
• 925669-13-2 1-(3-amino-2-thienyl)-2-(2-bromo-4,5-dimethoxyphenyl)ethanone 
• 925669-12-1 1-(3-amino-2-thienyl)-2-(2-bromo-4,5-dimethylphenyl)ethanone 
• 925669-11-0 1-(3-amino-2-thienyl)-2-(2-bromophenyl)ethanone 

Relevant academic research and scientific papers

Synthesis and chemistry of 4,5-dihydrothieno[3,2-b]pyrrol-6-ones - A heteroindoxyl

(Chemical Equation Presented) Flash vacuum pyrolysis (FVP) of 2-acetyl-3-azidothiophene gives 3-methylthieno[3,2-c]isoxazole as the major product at a furnace temperature of 350°C whereas at temperatures above 550°C the new heteroindoxyl 4,5-dihydrothieno[3,2-b]pyrrol-6-one is exclusively formed. The heteroindoxyl exists predominantly as the keto tautomer. It is O-protonated by TFA, N-acetylated by acetic anhydride, N-nitrosated by nitrous acid, and provides an N-methylene Meldrum's acid derivative on treatment with methoxymethylene Meldrum's acid. Reactions of 4,5-dihydrothieno[3,2-b] pyrrol-6-one with diazonium salts, with isatin, and with dimethyl acetylenedicarboxylate take place at the methylene position to provide a hydrazone, an indirubin analogue, and a succinate derivative, respectively. Oxidation of 4,5-dihydrothieno[3,2-b]pyrrol-6-one gives a heteroindigotin, which shows a hypsochromic shift in the UV spectrum, relative to indigotin itself.

Factors Affecting the Rates of Thermal Decomposition of Azidothiophenes

The thermolysis rate of 4-methoxy-1-azidobenzene reveals that the methoxy group increases the rate much less than the endocyclic sulfur does in 3-azidothiophene.With 3-azidothiophene, the neighbouring groups 2-acetyl and 2-nitro enhanced the rate in decalin solution only 5- and 17-fold, respectively, whereas in azidobenzene the corresponding enhancements are 413 and 1060.It is argued that the preferred electron distribution in the transition state for decomposition of 3-azidothiophene is not consistent with that required for effective neighbouring group participation. 2-Cyano and 2-methoxycarbonyl substituents, which are not known as effective neighbouring groups in thermal decompositions of azides, have very little effect on the rate for 3-azidothiophene.