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Trifluoromethyl hypofluorite

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Trifluoromethyl hypofluorite
  Carbon, C  Oxygen, O  Fluorine, F
Names
Preferred IUPAC name Trifluoromethyl hypofluorite
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.157 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/CF4O/c2-1(3,4)6-5Key: SMBZJSVIKJMSFP-UHFFFAOYSA-N
  • InChI=1/CF4O/c2-1(3,4)6-5Key: SMBZJSVIKJMSFP-UHFFFAOYAC
SMILES
  • FC(F)(F)OF
Properties
Chemical formula 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 , 100 kPa). ☒N (what is  ?) Infobox references
Chemical compound

Trifluoromethyl hypofluorite is an organofluorine compound with the chemical formula CF3OF. It exists as a colorless gas at room temperature and is highly toxic. 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:

2 F2 + CO → CF3OF

The gas hydrolyzes only slowly at neutral pH.

Use in organic chemistry

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

CF3OF + CH2CH2 → CF3OCH2CH2F

References

  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.
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