Trifluoromethyl hypofluorite

Trifluoromethyl hypofluorite is an organofluorine compound with the chemical formula CF₃OF. 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 a trifluoromethyl ester of hypofluorous acid. It is prepared by the reaction of fluorine gas with carbon monoxide:

2 F₂ + CO → CF₃OF

Trifluoromethyl hypofluorite

Carbon, C   Oxygen, O   Fluorine, F
Names
Preferred IUPAC name Trifluoromethyl hypofluorite
Identifiers
CAS Number	373-91-1 N
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	CF3OF
Molar mass	104.004012 g/mol
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 YN ?) 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