Chemical Properties
clear colorless to faintly colored liquid
Uses
2-Fluorobenzoyl Chloride (cas# 393-52-2) is a compound useful in organic synthesis.
Uses
2-Fluorobenzoyl chloride has been used in the preparation of 3-(
N-Hydroxycarbamimidoyl)-benzoic acid methyl ester. It has been used to develop an hollow-fiber liquid phase microextraction with
in situ derivatization method coupled with HPLC-UV for the determination of metformin hydrochloride in biological fluids.
General Description
Colorless liquid.
Air & Water Reactions
Decomposes in water to form HCl with generation of heat
Reactivity Profile
2-Fluorobenzoyl chloride is sensitive to moisture. Incompatible with water, alcohol, bases (including amines) and with oxidizing agents . May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
Fire Hazard
2-Fluorobenzoyl chloride is combustible.
Synthesis
Step I Synthesis of 2-fluorobenzoyl chloride (intermediate a): 0.714 mol (100 g) of 2-fluorobenzoic acid was added to 100 mL of toluene, and the mixture was heated to 50 °C before 5.7 mol (414 mL) of sulfoxide chloride was added slowly. The reaction mixture was reacted under reflux conditions for 7 hours. Upon completion of the reaction, the excess sulfoxide chloride was removed by evaporation to give 79 g of 2-fluorobenzoyl chloride in 70% yield.
References
[1] Phosphorus, Sulfur and Silicon and Related Elements, 1996, vol. 113, # 1-4, p. 179 - 207
[2] Journal of Organometallic Chemistry, 2005, vol. 690, # 17, p. 3918 - 3928
[3] Organic and Biomolecular Chemistry, 2009, vol. 7, # 23, p. 4886 - 4894
[4] Patent: EP2799437, 2014, A1. Location in patent: Paragraph 0055
[5] Patent: US2014/364431, 2014, A1. Location in patent: Paragraph 0186
