68295-42-1

Basic information

• Product Name: (4-fluorophenyl)(2-methylphenyl)methanone
• Synonyms: (4-fluorophenyl)(2-methylphenyl)methanone
• CAS NO: 68295-42-1
• Molecular Weight: 214.239
• Mol File: 68295-42-1.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: (4-fluorophenyl)(2-methylphenyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (4-fluorophenyl)(2-methylphenyl)methanone(68295-42-1)
• EPA Substance Registry System: (4-fluorophenyl)(2-methylphenyl)methanone(68295-42-1)

Safety Data

• Hazardous Substances Data: 68295-42-1(Hazardous Substances Data)

Upstream product

• 403-43-0 4-fluorobenzoyl chloride 
• 108-88-3 toluene 
• 624-31-7 4-tolyl iodide 
• 1194-02-1 4-fluorobenzonitrile 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 529-20-4 2-methylphenyl aldehyde 
• 1765-93-1 4-fluoroboronic acid 
• 133472-27-2 4-fluorophenylzinc chloride 
• 615-37-2 ortho-methylphenyl iodide 
• 201230-82-2 carbon monoxide 
• 16419-60-6 2-Methylphenylboronic acid 
• 17151-47-2 tributyl(4-fluorophenyl)stannane 
• 933-88-0 ortho-toluoyl chloride 
• 68971-87-9 (2-tolyl)tributyltin 

Downstream Products

• 1283147-07-8 (S)-2-(1-(4-(2-methylbenzoyl)phenyl)pyrrolidin-2-yl)acetonitrile 
• 1283147-06-7 (S)-(4-(2-(hydroxymethyl)pyrrolidin-1-yl)phenyl)(o-tolyl)methanone 

Relevant articles and documents

Efficient Synthesis of Diaryl Ketones by Nickel-Catalyzed Negishi Cross-Coupling of Amides by Carbon–Nitrogen Bond Cleavage at Room Temperature Accelerated by a Solvent Effect

The first Negishi cross-coupling of amides for the synthesis of versatile diaryl ketones by selective C?N bond activation under exceedingly mild conditions is reported. The cross-coupling was accomplished with bench-stable, inexpensive precatalyst [Ni(PPh3)2Cl2] that shows high functional-group tolerance and enables the synthesis of highly functionalized diaryl ketone motifs. The coupling occurred with excellent chemoselectivity favoring the ketone (cf. biaryl) products. Notably, this process represents the mildest conditions for amide N?C bond activation accomplished to date (room temperature, 10 min). Considering the versatile role of polyfunctional biaryl ketone linchpins in modern organic synthesis, availability, and excellent functional-group tolerance of organozinc reagents, this strategy provides a new platform for amide N?C bond/organozinc cross-coupling under mild conditions.

Arylation of Aldehydes to Directly Form Ketones via Tandem Nickel Catalysis

A nickel-catalyzed arylation of both aliphatic and aromatic aldehydes proceeds with air-stable (hetero)arylboronic acids, with an exceptionally wide substrate scope. The neutral condition tolerates acidic hydrogen and sensitive polar groups and also preserves α-stereocenters of some chiral aldehydes. Interestingly, this nickel(0) catalysis does not follow common 1,2-insertion of arylmetal species to aldehydes and β-hydrogen elimination.

Nickel-Catalyzed Negishi Cross-Coupling of N -Acylsuccinimides: Stable, Amide-Based, Twist-Controlled Acyl-Transfer Reagents via N-C Activation

This paper reports a room temperature, nickel-catalyzed Negishi cross-coupling of N -acylsuccinimides with arylzinc reagents via selective N-C bond cleavage enabled by amide bond twist. The reaction proceeds using a commercially available, air-stable Ni(II) precatalyst in the absence of additives under exceedingly mild conditions. Of broad interest, this report introduces N -acylsuccinimides as stable, crystalline, electrophilic, cost-effective, benign, amide-based acyl transfer reagents via acyl metal intermediates. The reaction selectivity is governed by half-twist of the amide bond in N -acylsuccinimides, thus opening the door for applications in metal-catalyzed manifolds via redox-neutral reaction pathways tuneable by amide bond distortion.