1010720-61-2

Basic information

• Product Name: 2-(2,2-difluoro-1-phenylvinyl)thiophene
• Synonyms: 2-(2,2-difluoro-1-phenylvinyl)thiophene
• CAS NO: 1010720-61-2
• Molecular Weight: 222.258
• Mol File: 1010720-61-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-(2,2-difluoro-1-phenylvinyl)thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,2-difluoro-1-phenylvinyl)thiophene(1010720-61-2)
• EPA Substance Registry System: 2-(2,2-difluoro-1-phenylvinyl)thiophene(1010720-61-2)

Safety Data

• Hazardous Substances Data: 1010720-61-2(Hazardous Substances Data)

Upstream product

• 10486-61-0 3-thienyl iodide 
• 1010720-48-5 tributyl-(β,β-difluoro-α-phenylvinyl)-stannane 
• 6453-99-2 3-benzoylthiophene 
• 1219454-89-3 2-((difluoromethyl)sulfonyl)pyridine 

Relevant articles and documents

Gem-difluoroolefination of diaryl ketones and enolizable aldehydes with difluoromethyl 2-pyridyl sulfone: New insights into the Julia-Kocienski reaction

The direct conversion of diaryl ketones and enolizable aliphatic aldehydes into gem-difluoroalkenes has been a long-standing challenge in organofluorine chemistry. Herein, we report efficient strategies to tackle this problem by using difluoromethyl 2-pyridyl sulfone as a general gem-difluoroolefination reagent. The gem-difluoroolefination of diaryl ketones proceeds by acid-promoted Smiles rearrangement of the carbinol intermediate; the gem-difluoroolefination is otherwise difficult to achieve through a conventional Julia-Kocienski olefination protocol under basic conditions due to the retro-aldol type decomposition of the key intermediate. Efficient gem-difluoroolefination of aliphatic aldehydes was achieved by the use of an amide base generated in situ (from CsF and tris(trimethylsilyl)amine), which diminishes the undesired enolization of aliphatic aldehydes and provides a powerful synthetic method for chemoselective gem-difluoroolefination of multi-carbonyl compounds. Our results provide new insights into the mechanistic understanding of the classical Julia-Kocienski reaction. What a gem! The gem-difluoroolefination of diaryl ketones was realized by an acid-promoted Julia-Kocienski olefination reaction at elevated temperatures. The gem-difluoroolefination of aliphatic aldehydes and chemoselective gem-difluoroolefination of dicarbonyl compounds was achieved with the use of an amide base generated in situ (see scheme).