Isolation and Characterization of Methyl Hypofluorite (CH3OF)

Moshe Kol, Shlomo Rozen*, Evan Appelman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Methyl hypofluorite (CH3OF) has been prepared by the reaction of elemental fluorine with methanol in acetonitrile or propionitrile at low temperature. It was removed from the reaction mixture in a stream of nitrogen and purified by fractional distillation. The compound is moderately long-lived, although the liquid has exploded upon rapid warming. The liquid compound has a freezing point of about -142 °C, and vapor pressure measurements indicate a normal boiling point of -32.6 ± 0.9 °C and an enthalpy of vaporization of 23.37 ± 0.26 kj/mol. The infrared spectrum of the vapor is consistent with the molecule being isostructural with CH3OH and CF3OF. The compound has also been characterized by mass spectrometry and by 1H, 19F, and 13C NMR spectrometries. This novel reagent adds across various double bonds to form the corresponding fluoro methoxy adducts, which are not easily accessible by other methods.

Original languageEnglish
Pages (from-to)2648-2651
Number of pages4
JournalJournal of the American Chemical Society
Volume113
Issue number7
DOIs
StatePublished - 1991

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