364-20-5

Basic information

• Product Name: 2-methylbenzoyl fluoride
• Synonyms: 2-methylbenzoyl fluoride
• CAS NO: 364-20-5
• Molecular Weight: 138.141
• Mol File: 364-20-5.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2-methylbenzoyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylbenzoyl fluoride(364-20-5)
• EPA Substance Registry System: 2-methylbenzoyl fluoride(364-20-5)

Safety Data

• Hazardous Substances Data: 364-20-5(Hazardous Substances Data)

Upstream product

• 607-86-3 2-methylbenzoic anhydride 
• 933-88-0 ortho-toluoyl chloride 
• 95-46-5 2-methylphenyl bromide 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 118-90-1 ortho-methylbenzoic acid 

Downstream Products

• 5448-38-4 N-benzyl-2-methylbenzamide 
• 529-19-1 2-Methylbenzonitrile 
• 1385064-56-1 3-phenyl-3-(trifluoromethyl)isochroman-1-one 
• 14309-60-5 1-phenylethynyltoluene 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 17113-82-5 1-methyl-2-(trimethylstannyl)benzene 
• 195062-59-0 2-methylphenylboronic acid pinacol ester 
• 68971-87-9 (2-tolyl)tributyltin 
• 41414-27-1 cyclohex-1-en-1-yl(o-tolyl)methanone 
• 131-58-8 2-Methylbenzophenone 

Relevant articles and documents

Benzoyl Fluorides as Fluorination Reagents: Reconstruction of Acyl Fluorides via Reversible Acyl C-F Bond Cleavage/Formation in Palladium Catalysis

This report describes the formation of value-added acyl fluorides by means of palladium-catalyzed acyl-exchange reactions between acyl fluorides and acid anhydrides. This method allows using a simple and commercially available acyl fluoride, benzoyl fluoride, as the fluoride source for the easy and efficient preparation of a variety of more complex acyl fluorides. The results of this study suggest that this reaction proceeds via a reversible acyl C-F bond cleavage/formation at the palladium center.

N-Heterocyclic Carbene Catalyzed Photoenolization/Diels–Alder Reaction of Acid Fluorides

The combination of light activation and N-heterocyclic carbene (NHC) organocatalysis has enabled the use of acid fluorides as substrates in a UVA-light-mediated photochemical transformation previously observed only with aromatic aldehydes and ketones. Stoichiometric studies and TD-DFT calculations support a mechanism involving the photoactivation of an ortho-toluoyl azolium intermediate, which exhibits “ketone-like” photochemical reactivity under UVA irradiation. Using this photo-NHC catalysis approach, a novel photoenolization/Diels–Alder (PEDA) process was developed that leads to diverse isochroman-1-one derivatives.

Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions

Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C-F bond cleavage and C-Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation.