893734-56-0

Basic information

• Product Name: 3'-(TRIFLUOROMETHYL)[1,1'-BIPHENYL]-4-CARBONITRILE
• Synonyms: AKOS BAR-0680;3'-(TRIFLUOROMETHYL)[1,1'-BIPHENYL]-4-CARBONITRILE;4-[3-(Trifluoromethyl)phenyl]benzonitrile
• CAS NO: 893734-56-0
• Molecular Formula: C14H8F3N
• Molecular Weight: 247.22
• Mol File: 893734-56-0.mol

Chemical Properties

• Boiling Point: 339.0±42.0 °C(Predicted)
• Appearance: /
• Density: 1.28±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3'-(TRIFLUOROMETHYL)[1,1'-BIPHENYL]-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-(TRIFLUOROMETHYL)[1,1'-BIPHENYL]-4-CARBONITRILE(893734-56-0)
• EPA Substance Registry System: 3'-(TRIFLUOROMETHYL)[1,1'-BIPHENYL]-4-CARBONITRILE(893734-56-0)

Safety Data

• Hazardous Substances Data: 893734-56-0(Hazardous Substances Data)

Upstream product

• 1423-26-3 (meta-(trifluoromethyl)phenyl)boronic acid 
• 623-03-0 4-Cyanochlorobenzene 

Relevant articles and documents

Palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides by carbon-nitrogen bond activation

Palladium-catalyzed Suzuki-Miyaura cross-coupling or aryl halides is widely employed in the synthesis of many important molecules in synthetic chemistry, including pharmaceuticals, polymers and functional materials. Herein, we disclose the first palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides for the synthesis of biaryls through the selective activation of the N-C(O) bond of amides. This new method relies on the precise sequence engineering of the catalytic cycle, wherein decarbonylation occurs prior to the transmetallation step. The reaction is compatible with a wide range of boronic acids and amides, providing valuable biaryls in high yields (>60 examples). DFT studies support a mechanism involving oxidative addition, decarbonylation and transmetallation and provide insight into high N-C(O) bond activation selectivity. Most crucially, the reaction establishes the use of palladium catalysis in the biaryl Suzuki-Miyaura cross-coupling of the amide bond and should enable the design of a wide variety of cross-coupling methods in which palladium rivals the traditional biaryl synthesis from aryl halides and pseudohalides.

Copper + nickel-in-charcoal (Cu-Ni/C): A bimetallic, heterogeneous catalyst for cross-couplings

(Chemical Equation Presented) A new heterogeneous catalyst composed of copper and nickel oxide particles supported within charcoal has been developed. It catalyzes cross-couplings that traditionally use palladium, nickel, or copper, including Suzuki-Miyaura reactions, Buchwald-Hartwig aminations, vinylalane alkylations, etherifications of aryl halides, aryl halide reductions, asymmetric conjugate reductions of activated olefins, and azide-alkyne "click" reactions.