Trifluoromethyl hypofluorite
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| Identifiers | |||
|---|---|---|---|
373-91-1  | |||
| ChemSpider | 71322 | ||
| Jmol interactive 3D | Image | ||
| PubChem | 78989 | ||
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| 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 | |||
| Main hazards | Toxic | ||
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
(what is  ?) | |||
| Infobox references | |||
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 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.[2] Behaving like a pseudohalogen, it adds to ethylene to give the ether:
- CF3OF + CH2CH2 → CF3OCH2CH2F
References
- ↑ 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.
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