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

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

• 118-90-1 ortho-methylbenzoic acid 
• 130250-61-2 2-methyl-N-methoxy-N-methylbenzamide 
• 352-13-6 4-flourophenylmagnesium bromide 
• 932-31-0 ortho-tolylmagnesium bromide 
• 352-34-1 4-fluoro-1-iodobenzene 
• 201230-82-2 carbon monoxide 
• 108-88-3 toluene 
• 133472-27-2 4-fluorophenylzinc chloride 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 933-88-0 ortho-toluoyl chloride 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 529-20-4 2-methylphenyl aldehyde 
• 615-37-2 ortho-methylphenyl iodide 
• 1765-93-1 4-fluoroboronic acid 

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.

Photoenolization/nucleophilic addition enables direct access to 3-alkyl-3-hydroxy-indolin-2-ones

A light-driven, catalyst- and additive-free photoenolization/nucleophilic addition reaction for the synthesis of 3-benzyl-3-hydroxyindolin-2-ones is presented. In this reaction, 2-methylbenzophenones undergo light-induced enolization process to afford hydroxy-o-quinodimethanes (hydroxy-o-QDMs), which are then immediately captured by the electrophilic isatins. The reaction utilizes green and clean light energy to realize the C–H activation of the inert benzyl position of 2-methylbenzophenones. This method tolerates a wide scope of substrates and provides concise access to a series of novel 3-benzyl-3-hydroxyindolin-2-ones with 60–99% yields.

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.

A general approach to intermolecular carbonylation of arene C-H bonds to ketones through catalytic aroyl triflate formation

The development of metal-catalysed methods to functionalize inert C-H bonds has become a dominant research theme in the past decade as an approach to efficient synthesis. However, the incorporation of carbon monoxide into such reactions to form valuable ketones has to date proved a challenge, despite its potential as a straightforward and green alternative to Friedel-Crafts reactions. Here we describe a new approach to palladium-catalysed C-H bond functionalization in which carbon monoxide is used to drive the generation of high-energy electrophiles. This offers a method to couple the useful features of metal-catalysed C-H functionalization (stable and available reagents) and electrophilic acylations (broad scope and selectivity), and synthesize ketones simply from aryl iodides, CO and arenes. Notably, the reaction proceeds in an intermolecular fashion, without directing groups and at very low palladium-catalyst loadings. Mechanistic studies show that the reaction proceeds through the catalytic build-up of potent aroyl triflate electrophiles.

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.

At normal pressure fragrant ketone nickel catalytic synthesis method

The invention discloses a method for synthesizing diarylketone under the catalysis of nickel at normal pressure. The method comprises the steps of enabling aryl iodide, arylboronic acid and carbon monoxide to be subjected to direct cross-coupling reaction in a solvent polyethylene glycol or a water solution of polyethylene glycol under the catalysis of a nickel catalyst and the combined action of alkaline and acid at normal pressure to prepare a diarylketone compound. The method has the advantages of wide catalyst source, low price, little toxicity, reaction at normal pressure, high selectivity, no need of ligands in reaction, good activity, good functional group compatibility, wide substrate application range, wide substrate source, stable substrate, green and recyclable reaction medium and the like. The separation yield of target products is up to 93% under an optimized reaction condition.

At normal pressure fragrant ketone copper catalytic synthesis method

The invention discloses a method of synthesizing diaryl ketone under normal pressure by virtue of copper catalysis. The method is as follows: in a solvent alcohol or aqueous liquor of alcohol, under action of alkali and acid, adding a copper catalyst, alkyl iodide, alkyl boric acid and carbon monoxide to directly carry out crossed coupling reaction to prepare diaryl ketone compounds. According to the invention, the method of preparing diaryl ketone compounds by carbonylation Suzuki coupling reaction has the advantages as follows: the catalyst is wide in source, cheap and small in toxicity; the reaction is free of ligand in reaction and good in activity; the reaction is carried out under the normal pressure and selectivity is high; a substrate source is wide and stable; functional group compatibility is good and scope of application for the substrate is wide; a reaction medium is environment-friendly and recyclable. Under the condition of optimizing reaction conditions, the target product separating yield is 95%.

Light-Driven Carboxylation of o-Alkylphenyl Ketones with CO2

o-Alkylphenyl ketones undergo a C-C bond forming carboxylation reaction with CO2 simply upon irradiation with UV light or even solar light. The reaction presents a clean process exploiting light energy as the driving force for carboxylation of organic molecules with CO2.

Metal-free efficient cross coupling of aromatic aldehydes with aryldiazonium tetrafluoroborates using DTBP as a radical initiator

A highly efficient, metal-free, one-pot radical route to access diaryl ketones from aromatic aldehydes is reported. The protocol renders cross coupling of aromatic aldehydes with aryl diazonium tetrafluoroborates using inexpensive di-tert-butylperoxide (DTBP) as a radical initiator under mild conditions. The reaction offers a convenient alternative to the Friedel-Crafts acylation for the synthesis of diaryl ketones.

Transition-metal-free, ambient-pressure carbonylative cross-coupling reactions of aryl halides with potassium aryltrifluoroborates

We disclose an unprecedented transition-metal-free carbonylative cross coupling of aryl halides with potassium aryl trifluoroborates even at atmospheric pressure of carbon monoxide. This protocol is efficient, operationally simple, and shows wide scope with regard to both aryl halides and potassium aryl trifluoroborates containing a series of active functional groups.