91748-21-9

Basic information

• Product Name: 4'-TRIFLUOROMETHYL-BIPHENYL-2-CARBONITRILE
• Synonyms: 2-(4-TRIFLUOROMETHYLPHENYL)- BENZONITRILE;4-(TRIFLUOROMETHYL)-2'-BIPHENYLCARBONITRILE;4'-(TRIFLUOROMETHYL)[1,1'-BIPHENYL]-2-CARBONITRILE;4'-TRIFLUOROMETHYL-BIPHENYL-2-CARBONITRILE;AKOS BAR-1257;Trifluoromethylbiphenylcarbonitrile
• CAS NO: 91748-21-9
• Molecular Formula: C14H8F3N
• Molecular Weight: 247.22
• Mol File: 91748-21-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4'-TRIFLUOROMETHYL-BIPHENYL-2-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-TRIFLUOROMETHYL-BIPHENYL-2-CARBONITRILE(91748-21-9)
• EPA Substance Registry System: 4'-TRIFLUOROMETHYL-BIPHENYL-2-CARBONITRILE(91748-21-9)

Safety Data

• Statements: 20/21/22
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• Hazardous Substances Data: 91748-21-9(Hazardous Substances Data)

Upstream product

• 2042-37-7 o-cyanobromobenzene 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 873-32-5 2-Chlorobenzonitrile 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 138642-62-3 2-Cyanophenylboronic acid 
• 455-13-0 4-Iodobenzotrifluoride 
• 172732-52-4 o-cyanophenylboronic acid-1,3-propylene glycol ester 
• 100-47-0 benzonitrile 

Downstream Products

• 84392-17-6 4'-(trifluoromethyl)-2-biphenylcarboxylic acid 

Relevant articles and documents

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.

Novel syntheses of fluorenones via nitrile-directed palladium-catalyzed C-H and dual C-H bond activation

Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.

Preparation of polyfunctional arylmagnesium, arylzinc, and benzylic zinc reagents by using magnesium in the presence of LiCl

The presence of LiCl considerably facilitates the insertion of magnesium into various aromatic and heterocyclic bromides. Several functional groups, such as -OBoc, -OTs, -Cl, -F, -CF3, -OMe, -NMe2, and -N 2NR2, are well tolerated. The presence of a cyano group leads in some cases to competitive reduction of the organic halide to the corresponding ArH compound. The presence of sensitive groups such as methyl or ethyl ester is tolerated upon in situ trapping of the intermediate magnesium reagent with ZnCl2. This method can also be applied to the preparation of functionalized benzylic zinc reagents from benzylic chlorides. In the case of di- or tribromoaryl derivatives, directing groups such as -OPiv, -OTs, -N2NR2, or -OAc orient the zinc insertion (Zn/LiCl) to the ortho-position, while the reaction with Mg/LiCl or Mg/LiCl/ZnCl 2 leads to regioselective insertion into the para-carbon-bromine bond. Large-scale experiments (20-100 mmol) for all of the metalation procedures are described.