Trifluoromethyl hypofluorite

Trifluoromethyl hypofluorite is an organofluorine compound with the formula CF
3OF. 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 prepared by the reaction of fluorine gas with carbon monoxide:

2 F2 + CO → CF3OF
Trifluoromethyl hypofluorite
Names
Preferred IUPAC name
Trifluoromethyl hypofluorite
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.157
  • 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
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
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 ?)
Infobox references

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.[2] Behaving like a pseudohalogen, it adds to ethylene to give the ether:

CF3OF + CH2CH2 → CF3OCH2CH2F

References
  1. Cady, G (1966). "Trifluoromethyl Hypofluorite". Inorganic Syntheses. 8: 168. doi:10.1002/9780470132395.ch43.
  2. Middleton, W. J.; Bingham, E. M. (1980). "α-Fluorination of carbonyl compounds with trifluoromethyl hypofluorite". Journal of the American Chemical Society. 102: 4845–6. doi:10.1021/ja00534a053.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.