Formyl Fluoride

[1493-02-3] CHFO (MW 48.02) InChI = 1S/CHFO/c2-1-3/h1H InChIKey = NHGVZTMBVDFPHJ-UHFFFAOYSA-N (formylating agent for organic compounds1) Physical Data: bp −29 °C; mp −142 °C. Preparative Methods: HCOF, one of the stable halides of formic acid, is generally prepared by combining Formic Acid with a fluorinating agent.1 A variety of reagents such as Benzoyl Chloride/Potassium Fluoride,2 benzoyl fluoride,3 benzoyl chloride/KHF2,4 cyanuric fluoride,5 and tetramethyl-α-fluoroenamine6 has been employed for this purpose. HCOF was also successfully prepared by reaction of Acetic Formic Anhydride with Hydrogen Fluoride at atmospheric pressure with continuous removal of formyl fluoride.7 Combining benzoyl fluoride with sodium formate is another worthy procedure for its preparation.5 Ozonolysis of 1,2-difluoroethylene and vinyl fluoride offers a potential new route to HCOF.8 The best result among all the methods was achieved by fluorinating formic acid with tetramethyl-α-fluoroenamine.6 A 100% yield was reported. Handling, Storage, and Precautions: decomposes rapidly at room temperature into CO and HF.1b The reaction is autocatalytic since the HF formed initially catalyzes the decarbonylation. Therefore, acid-free HCOF should be stored at low temperature (of the order of −70 °C) under pressure over anhydrous sodium fluoride, which is able to absorb the hydrogen fluoride formed in decomposition. Use in a fume hood.