Trifluoromethyl hypofluorite

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

Trifluoromethyl hypofluorite is an organofluorine compound with the chemical formula C F ₃ OF. Its chemical structure resembles methanol, but every hydrogen atom is replaced by a fluorine atom. Trifluoromethyl hypofluorite is a toxic gas at room temperature, exploding when condensed; but in small quantities the compound is useful for certain fluorination reactions in organic chemistry.

Structure

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), the trifluoromethyl ester of hypofluorous acid.

Generation

It is prepared by the reaction of fluorine gas with carbon monoxide, ^[1] over a cesium fluoride catalyst:

2 F₂ + CO → CF₃OF

The reaction is too dangerous for commercial use. The process is highly exothermic, each reagent is either extremely toxic or corrosive, and the product is liable to explode when condensed. ^[2]

Reactions

The gas hydrolyzes only slowly at neutral pH.

In organic chemistry, the compound adds electrophilic fluorine to multiple bonds. It has been used for the preparation of α-fluoroketones from silyl enol ethers ^[3] and N-fluoroamides from iminoethers. It directly fluorinates activated arenes. ^[2] Behaving like a pseudohalogen, CF₃OF adds to ethylene to give the ether:^{[ citation needed ]}

CF₃OF + CH₂CH₂ → CF₃OCH₂CH₂F

With saturated compounds, it usually performs an indiscriminate radical fluorination. But radical traps cause the reaction to instead selectively fluorinate tertiary carbons. ^[2]

References

1. Cady, G (1966). "Trifluoromethyl Hypofluorite". Inorganic Syntheses. Vol. 8. p. 168. doi:10.1002/9780470132395.ch43. ISBN   978-0-470-13167-1.
2. Hesse, Robert H. (2001). "Trifluoromethyl hypofluorite". Encyclopedia of Reagents for Organic Synthesis. Wiley. doi:10.1002/047084289X.rt251. ISBN   0-471-93623-5.
3. Middleton, W. J.; Bingham, E. M. (1980). "α-Fluorination of carbonyl compounds with trifluoromethyl hypofluorite". Journal of the American Chemical Society. 102 (14): 4845–6. Bibcode:1980JAChS.102.4845M. doi:10.1021/ja00534a053.