1010720-53-2

Basic information

• Product Name: 1-(2,2-difluoro-1-phenylvinyl)-4-(trifluoromethyl)benzene
• Synonyms: 1-(2,2-difluoro-1-phenylvinyl)-4-(trifluoromethyl)benzene
• CAS NO: 1010720-53-2
• Molecular Weight: 284.228
• Mol File: 1010720-53-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1-(2,2-difluoro-1-phenylvinyl)-4-(trifluoromethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,2-difluoro-1-phenylvinyl)-4-(trifluoromethyl)benzene(1010720-53-2)
• EPA Substance Registry System: 1-(2,2-difluoro-1-phenylvinyl)-4-(trifluoromethyl)benzene(1010720-53-2)

Safety Data

• Hazardous Substances Data: 1010720-53-2(Hazardous Substances Data)

Upstream product

• 1010720-48-5 tributyl-(β,β-difluoro-α-phenylvinyl)-stannane 
• 455-13-0 4-Iodobenzotrifluoride 
• 60664-82-6 1-(Diazo-phenyl-methyl)-4-trifluoromethyl-benzene 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 433-06-7 2,2,2-Trifluoroethyl p-toluenesulfonate 
• 1256278-62-2 2,2-difluoro-1-phenylvinyl 4-methylbenzenesulfonate 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 728-86-9 phenyl[4-(trifluoromethyl)phenyl]methanone 
• 1219454-89-3 2-((difluoromethyl)sulfonyl)pyridine 
• 60664-70-2 4-(Trifluormethyl)-benzophenon-hydrazon 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 100-52-7 benzaldehyde 
• 98-80-6 phenylboronic acid 

Relevant articles and documents

Dehalogenative Cross-Coupling of gem-Difluoroalkenes with Alkyl Halides via a Silyl Radical-Mediated Process

Herein, we describe a convenient general protocol for monofluoroalkenylation reactions of alkyl bromides involving cooperative visible-light photoredox catalysis and halogen abstraction. Mechanistic experiments showed that the products were generated by selective cross-coupling of aliphatic radicals with fluoroalkenyl radicals. Silyl radical-mediated halogen abstraction enabled the protocol to be used for the monofluoroalkenylation of a broad range of alkyl and heteroaryl halides. The protocol could be carried out on a gram scale and was applied to cholesterol, indicating its utility for late-stage monofluoroalkenylation reactions.

Trifluoromethylation and Monofluoroalkenylation of Alkenes through Radical–Radical Cross-Coupling

The first visible-light-induced trifluoromethylation and monofluoroalkenylation of simple alkenes via a challenging radical–radical cross-coupling step was achieved. This method provided a mild, step-economical and redox-neutral route to privileged two different fluorinated difunctionalized allyl compounds. The utility of this method is illustrated by late-stage modification of medically important molecules.

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).