Hypofluorousacid (8CI,9CI)

Chemical Properties

Hypofluoric acid is a relatively novel oxidant. The OF bond is unstable; oxygen is connected to fluorine, which is more electronegative than oxygen, so that the oxygen in it is biased to be positively charged. It is a highly electrophilic oxygen-donating reagent (the oxygen in hypofluoric acid) and strong applicability.

Uses

Hypofluoric acid is generally used as an oxygen-donating reagent or a hydroxylating reagent in its acetonitrile solution.

Application

The HOF.MeCN complex is used for tertiary hydroxylations, epoxidations, and oxidations of amines, alcohols, ketones, aromatic compounds, and sulfides.

Definition

ChEBI: Hypofluorous acid is a fluorine oxoacid. It is a conjugate acid of a hypofluorite.

storage

HOF is a very unstable substance and of little use in synthetic  chemistry. Neat liquid HOF can be unpredictably explosive at temperatures above -40 °C. Its acetonitrile  complex is much more stable but nevertheless has to be prepared in situ and, for all practical purposes, has  to be reacted soon after its formation. The concentration of the reagent is determined iodometrically  (HOF + 2KI -> I2 + KF + KOH). Both forms of the hypofluorous acid may be toxic and should be treated  accordingly. Use in a fume hood.

Raw materials

Preparation Products