Trifluoromethyl hypofluorite

Trifluoromethyl hypofluorite

Identifiers
CAS Number	373-91-1
ChemSpider	71322
Jmol interactive 3D	Image
PubChem	78989
InChI 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
SMILES FC(F)(F)OF
Properties
Chemical formula	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).
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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

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 hypo fluorite". Journal of the American Chemical Society 102: 4845–6. doi:10.1021/ja00534a053.