113649-19-7

Basic information

• Product Name: 3-Thiophenecarboxylic acid, 2-(methylthio)-5-phenyl-, methyl ester
• CAS NO: 113649-19-7
• Molecular Formula: C13H12O2S2
• Molecular Weight: 264.369
• Mol File: 113649-19-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-Thiophenecarboxylic acid, 2-(methylthio)-5-phenyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Thiophenecarboxylic acid, 2-(methylthio)-5-phenyl-, methyl ester(113649-19-7)
• EPA Substance Registry System: 3-Thiophenecarboxylic acid, 2-(methylthio)-5-phenyl-, methyl ester(113649-19-7)

Safety Data

• Hazardous Substances Data: 113649-19-7(Hazardous Substances Data)

Upstream product

• 75-15-0 carbon disulfide 
• 77903-44-7 t-2-Phenyl-c-2-(trimethylsiloxy)-r-1-cyclopropancarbonsaeure-methylester 
• 74-88-4 methyl iodide 

Relevant articles and documents

Thiophene Derivatives from Methyl 2-Siloxycyclopropanecarboxylates by Novel 1,3- and 1,2-Sigmatropic Rearrangements

Ester enolates, generated with LDA from methyl 2-siloxycyclopropanecarboxylates 1, and carbon disulfide/methyl iodide afford methyl dihydrothiophenecarboxylates 3.Depending on the substitution pattern, these can be converted into methyl 3-thiophenecarboxylates 7 either by F3B-OEt2-promoted Wagner-Meerwein shift of an alkyl group or by acid-induced elimination of trimethylsilanol.The mechanism of this surprising ring enlargement of cyclopropanes leading to heterocycles is described as an anionic 1,3-sigmatropic rearrangement (10-->11) which even takes place at -78 deg C.Similar reaction conditions convert methyl cyclopropanecarboxylate 13, having no siloxy function, into the γ,δ-unsaturated dithiocarboxylate 14.For its formation an anionic homo-1,5-sigmatropic hydrogen shift is suggested as the key step.On the other hand, methyl 2,2-diphenylcyclopropanecarboxylate (17) affords the ring opening product 19, which must be formed by deprotonation at C-3 of an intermediate cyclopropane derivative.