Trifluoromethyl hypofluorite

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Trifluoromethyl hypofluorite
CF3OF.png
Identifiers
CAS number 373-91-1 N
PubChem 78989
ChemSpider 71322
Jmol-3D images Image 1
Properties
Molecular formula OCF
4
Molar mass 104.004012
Appearance Colourless gas
Melting point −213 °C (−351.4 °F; 60.1 K)
Boiling point −95 °C (−139 °F; 178 K)
Hazards
Main hazards Toxic
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N
Infobox references

Trifluoromethyl hypofluorite is an organofluorine compound with the formula CF
3
OF
. It exists as a colorless gas at room temperature and is highly toxic.[1] It is a rare example of a hypofluorite (compound with an O-F bond). It is prepared by the fluorination of carbon monoxide:

2 F2 + CO → CF3OF

The gas hydrolyzes only slowly at neutral pH.

Use in organic chemistry[edit]

The compound is a source of electrophilic fluorine. It has been used for the preparation of α-fluoroketones from silyl enol ethers.[2] Behaving like a pseudohalogen, it adds to ethylene to give the ether:

CF3OF + CH2CH2 → CF3OCH2CH2F

References[edit]

  1. ^ Cady, G. "Trifluoromethyl Hypofluorite" Inorganic Syntheses, 1966, Volume 8, p. 168. doi:10.1002/9780470132395.ch43
  2. ^ Middleton, W. J.; Bingham, E. M. "α-Fluorination of carbonyl compounds with trifluoromethyl hypo fluorite" Journal of the American Chemical Society, 1980, vol. 102, pp. 4845-6. doi:10.1021/ja00534a053