709-69-3

Basic information

• Product Name: Benzoic acid, 4-(fluorocarbonyl)-, methyl ester (9CI)
• Synonyms: Benzoic acid, 4-(fluorocarbonyl)-, methyl ester (9CI)
• CAS NO: 709-69-3
• Molecular Formula: C₉H₇FO₃
• Molecular Weight: 182.1484832
• Product Categories: ACIDHALIDE
• Mol File: 709-69-3.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoic acid, 4-(fluorocarbonyl)-, methyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-(fluorocarbonyl)-, methyl ester (9CI)(709-69-3)
• EPA Substance Registry System: Benzoic acid, 4-(fluorocarbonyl)-, methyl ester (9CI)(709-69-3)

Safety Data

• Hazardous Substances Data: 709-69-3(Hazardous Substances Data)

Upstream product

• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 
• 1571-08-0 methyl 4-formylbenzoate 
• 1679-64-7 Monomethyl terephthalate 

Downstream Products

• 171364-80-0 methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 729-17-9 methyl 4-(4'-methoxyphenyl)benzoate 
• 71616-84-7 4-methoxycarbonyl-4'-methoxybenzophenone 
• 905966-40-7 methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 1616766-87-0 methyl 4-((triisopropylsilyl)ethynyl)benzoate 
• 42497-80-3 methyl 4-(phenylethynyl)benzoate 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 65488-27-9 (4-carbomethoxyphenyl)trimethylstannane 
• 1325725-67-4 (R)-methyl 4-(2-oxo-3-phenyltetrahydrofuran-3-yl)carbonyl benzoate 

Relevant articles and documents

Rapid and column-free syntheses of acyl fluorides and peptides usingex situgenerated thionyl fluoride

Thionyl fluoride (SOF2) was first isolated in 1896, but there have been less than 10 subsequent reports of its use as a reagent for organic synthesis. This is partly due to a lack of facile, lab-scale methods for its generation. Herein we report a novel protocol for theex situgeneration of SOF2and subsequent demonstration of its ability to access both aliphatic and aromatic acyl fluorides in 55-98% isolated yields under mild conditions and short reaction times. We further demonstrate its aptitude in amino acid couplings, with a one-pot, column-free strategy that affords the corresponding dipeptides in 65-97% isolated yields with minimal to no epimerization. The broad scope allows for a wide range of protecting groups and both natural and unnatural amino acids. Finally, we demonstrated that this new method can be used in sequential liquid phase peptide synthesis (LPPS) to afford tri-, tetra-, penta-, and decapeptides in 14-88% yields without the need for column chromatography. We also demonstrated that this new method is amenable to solid phase peptide synthesis (SPPS), affording di- and pentapeptides in 80-98% yields.

Deoxyfluorination of Carboxylic, Sulfonic, Phosphinic Acids and Phosphine Oxides by Perfluoroalkyl Ether Carboxylic Acids Featuring CF2O Units

The deoxyfluorination of carboxylic, sulfonic, phosphinic acids and phosphine oxides is a fundamentally important approach to access acyl fluorides, sulfonyl fluorides and phosphoric fluorides, thus the development of inexpensive, stable, easy-to-handle, versatile, and efficient deoxyfluorination reagents is highly desired. Herein, we report the use of potassium salts of perfluoroalkyl ether carboxylic acids (PFECA) featuring CF2O units as deoxyfluorination reagents, which are generated mainly as by-products in the manufacture of hexafluoropropene oxide (HFPO). The synthesis of acyl fluorides, sulfonyl fluorides and phosphoric fluorides can be realized via carbonic difluoride (COF2) generated in situ from thermal degradation of the PFECA salt.

Deoxyfluorination of Carboxylic Acids with KF and Highly Electron-Deficient Fluoroarenes

A deoxyfluorination reaction of carboxylic acids using potassium fluoride (KF) and highly electron-deficient fluoroarenes is reported here, giving acyl fluorides in moderate to excellent yield (57-92% based on NMR integration and 34-95% for isolated examples).