Trifluoromethyl hypofluorite

Trifluoromethyl hypofluorite is an organofluorine compound with the chemical formula CF3OF. 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 can be seen as a similar chemical compound to methanol where every hydrogen atom is replaced by a fluorine atom. It is a trifluoromethyl ester of hypofluorous acid. It is prepared by the reaction of fluorine gas with carbon monoxide:

Trifluoromethyl hypofluorite
  Carbon, C
  Oxygen, O
  Fluorine, F
Names
Preferred IUPAC name
Trifluoromethyl hypofluorite
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.157 Edit this at Wikidata
  • InChI=1S/CF4O/c2-1(3,4)6-5
    Key: SMBZJSVIKJMSFP-UHFFFAOYSA-N
  • InChI=1/CF4O/c2-1(3,4)6-5
    Key: SMBZJSVIKJMSFP-UHFFFAOYAC
  • FC(F)(F)OF
Properties
CF3OF
Molar mass 104.004012 g/mol
Appearance Colourless gas
Melting point −213 °C (−351.4 °F; 60.1 K)
Boiling point −95 °C (−139 °F; 178 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N (what is checkY☒N ?)
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 (1966). "Trifluoromethyl Hypofluorite". Inorganic Syntheses. Vol. 8. p. 168. doi:10.1002/9780470132395.ch43. ISBN 978-0-470-13167-1.
  2. ^ Middleton, W. J.; Bingham, E. M. (1980). "α-Fluorination of carbonyl compounds with trifluoromethyl hypofluorite". Journal of the American Chemical Society. 102 (14): 4845–6. doi:10.1021/ja00534a053.