3D model (JSmol)
|Melting point||−213 °C (−351.4 °F; 60.1 K)|
|Boiling point||−95 °C (−139 °F; 178 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Trifluoromethyl hypofluorite is an organofluorine compound with the formula CF
3OF. 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 is prepared by the fluorination of 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
- Cady, G (1966). "Trifluoromethyl Hypofluorite". Inorganic Syntheses. 8: 168. doi:10.1002/9780470132395.ch43.
- Middleton, W. J.; Bingham, E. M. (1980). "α-Fluorination of carbonyl compounds with trifluoromethyl hypo fluorite". Journal of the American Chemical Society. 102: 4845–6. doi:10.1021/ja00534a053.