Trifluoromethyl hypofluorite

Trifluoromethyl hypofluorite
Identifiers
CAS Number	373-91-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	71322;
ECHA InfoCard	100.006.157
PubChem CID	78989;
CompTox Dashboard (EPA)	DTXSID4073174 ;
	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).
	(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 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.[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 hypofluorite". Journal of the American Chemical Society. 102: 4845–6. doi:10.1021/ja00534a053.

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[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.