893739-06-5

Basic information

• Product Name: 3-(1,1,1-trifluoroprop-2-en-2-yl)benzonitrile
• Synonyms: 3-(1,1,1-trifluoroprop-2-en-2-yl)benzonitrile
• CAS NO: 893739-06-5
• Molecular Weight: 197.16
• Mol File: 893739-06-5.mol

Chemical Properties

• CAS DataBase Reference: 3-(1,1,1-trifluoroprop-2-en-2-yl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1,1,1-trifluoroprop-2-en-2-yl)benzonitrile(893739-06-5)
• EPA Substance Registry System: 3-(1,1,1-trifluoroprop-2-en-2-yl)benzonitrile(893739-06-5)

Safety Data

• Hazardous Substances Data: 893739-06-5(Hazardous Substances Data)

Upstream product

• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 150255-96-2 (3‐cyanophenyl)boronic acid 
• 2730-62-3 2-chloro-1,1,1-trifluoropropene 

Relevant articles and documents

Palladium-catalyzed Suzuki–Miyaura reaction of fluorinated vinyl chloride: a new approach for synthesis α and α,β-trifluoromethylstyrenes

A mild and efficient palladium-catalyzed cross-coupling between fluorinated vinyl chloride and arylboronic acids is described. The use of ligand B successfully overcomes the strong electronic withdrawing of trifluoromethylated substrates and allows the efficient synthesis of a wide range of α and α,β-trifluoromethyl containing olefins. By using this method, the key intermediate for synthesis of Efavirenz can be obtained in a simple route. The efficient conversion of two freon molecules into useful α and α,β-trifluoromethyl containing olefins is a useful route in organic chemistry.

Site-Selective Defluorinative sp3C-H Alkylation of Secondary Amides

A site-selective defluorinative sp3 C-H alkylation of secondary amides that rapidly and reliably incorporates gem-difluoroalkene motifs into previously unfunctionalized sp3 sites is disclosed. This protocol is distinguished by its mild conditions, wide scope, and exquisite site-selectivity, thus unlocking a new platform to introduce carbonyl isosteres at saturated hydrocarbon sites.

NiH-Catalyzed Migratory Defluorinative Olefin Cross-Coupling: Trifluoromethyl-Substituted Alkenes as Acceptor Olefins to Form gem-Difluoroalkenes

We report a NiH-catalyzed migratory defluorinative coupling between two electronically differentiated olefins. A broad range of unactivated donor olefins can be joined directly to acceptor olefins containing an electron-deficient trifluoromethyl substituent in both intra- and intermolecular fashion to form gem-difluoroalkenes. This migratory coupling shows both site- and chemoselectivity under mild conditions, with the formation of a tertiary or quaternary carbon center.

Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover

A benchtop stable, bifunctional reagent for the redox-neutral cyclopropanation of olefins has been developed. Triethylammonium bis(catecholato)iodomethylsilicate can be readily prepared on multigram scale. Using this reagent in combination with an organic photocatalyst and visible light, cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes, can be accomplished in a matter of hours. The reaction is highly tolerant of traditionally reactive functional groups (carboxylic acids, basic heterocycles, alkyl halides, etc.) and permits the chemoselective cyclopropanation of polyolefinated compounds. Mechanistic interrogation revealed that the reaction proceeds via a rapid anionic 3-exo-tet ring closure, a pathway consistent with experimental and computational data.

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