437-23-0

Basic information

• Product Name: Benzene, 1,1'-[(4-fluorophenyl)methylene]bis-
• CAS NO: 437-23-0
• Molecular Formula: C19H15F
• Molecular Weight: 262.327
• Mol File: 437-23-0.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-[(4-fluorophenyl)methylene]bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-[(4-fluorophenyl)methylene]bis-(437-23-0)
• EPA Substance Registry System: Benzene, 1,1'-[(4-fluorophenyl)methylene]bis-(437-23-0)

Safety Data

• Hazardous Substances Data: 437-23-0(Hazardous Substances Data)

Upstream product

• 427-39-4 (4-fluorophenyl)diphenylmethanol 
• 459-57-4 4-fluorobenzaldehyde 
• 71-43-2 benzene 
• 91-01-0 1,1-Diphenylmethanol 
• 1765-93-1 4-fluoroboronic acid 
• 119-61-9 benzophenone 
• 352-13-6 4-flourophenylmagnesium bromide 
• 1489331-54-5 bis(N,Ndiethylcarbamoyltelluro)-p-fluorophenylmethane 
• 456-19-9 4-fluorobenzal chloride 
• 587-79-1 4-fluorodiphenylmethane 
• 108-90-7 chlorobenzene 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 101-81-5 Diphenylmethane 
• 5433-76-1 diphenylmethyl phenyl sulfone 

Downstream Products

• 67096-50-8 α-H-Tetradecachloro-4-fluoro-triphenylmethan 

Relevant articles and documents

Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters

The synthesis of triarylmethanes via Pd-catalyzed Suzuki-Miyaura reactions between diarylmethyl 2,3,4,5,6-pentafluorobenzoates and aryl boronic acids is described. The system operates under mild conditions and has a broad substrate scope, including the coupling of diphenylmethanol derivatives that do not contain extended aromatic substituents. This is significant as these substrates, which result in the types of triarylmethane products that are prevalent in pharmaceuticals, have not previously been compatible with systems for diarylmethyl ester coupling. Furthermore, the reaction can be performed stereospecifically to generate stereoinverted products. On the basis of DFT calculations, it is proposed that the oxidative addition of the diarylmethyl 2,3,4,5,6-pentafluorobenzoate substrate occurs via an SN2 pathway, which results in the inverted products. Mechanistic studies indicate that oxidative addition of the diarylmethyl 2,3,4,5,6-pentafluorobenzoate substrates to (IPr)Pd(0) results in the selective cleavage of the O-C(benzyl) bond in part because of a stabilizing η3-interaction between the benzyl ligand and Pd. This is in contrast to previously described Pd-catalyzed Suzuki-Miyaura reactions involving phenyl esters, which involve selective cleavage of the C(acyl)-O bond, because there is no stabilizing η3-interaction. It is anticipated that this fundamental knowledge will aid the development of new catalytic systems, which use esters as electrophiles in cross-coupling reactions.

Nickel-Catalyzed C(sp3)-H Arylation of Diarylmethane Derivatives with Aryl Fluorides

A novel nickel-catalyzed C(sp3)-H arylation with nonactivated aryl fluorides is reported. The use of 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes) as a ligand was found to be critical to the success of the reaction. This new method enables the synthesis of a wide range of triarylmethane derivatives.

Synthesis of Di- and Triarylmethanes through Palladium-Catalyzed Reductive Coupling of N -Tosylhydrazones and Aryl Bromides

A palladium-catalyzed reductive coupling between N-tosylhydrazones and aryl bromides has been developed. The reaction provides an efficient method for the synthesis of diarylmethanes and triarylmethanes via the formation of C(sp2)-C(sp3) single bonds. This new methodology for the synthesis of diarylmethanes and triarylmethanes is featured by the ready availability of the starting materials, mild reaction conditions, and the tolerance of wide range of functional groups. The reaction follows a pathway including palladium carbene formation, migratory insertion, and reduction of the alkylpalladium(II) intermediate.