Formyl fluoride

Formyl fluoride
Formyl fluoride
Formyl fluoride
Formyl fluoride
Formyl fluoride
Names
Preferred IUPAC name
Formyl fluoride
Other names
Formic acid fluoride
Methanoyl fluoride
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/CHFO/c2-1-3/h1H checkY
    Key: NHGVZTMBVDFPHJ-UHFFFAOYSA-N checkY
  • InChI=1/CHFO/c2-1-3/h1H
    Key: NHGVZTMBVDFPHJ-UHFFFAOYAX
  • FC=O
Properties
CHFO
Molar mass 48.016 g·mol−1
Appearance Colorless gas
Melting point −142 °C (−224 °F; 131 K)
Boiling point −29 °C (−20 °F; 244 K)
Decomposes
Solubility in other solvents Chlorocarbons,
Freons
Structure
2.02 D[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic
Related compounds
Related compounds
 Formic acid
Hydrogen fluoride
Carbonyl fluoride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Formyl fluoride is the organic compound with the formula HC(O)F.

Preparation

HC(O)F was first reported in 1934.[2] Among the many preparations, a typical one involves the reaction of sodium formate with benzoyl fluoride (generated in situ from KHF2 and benzoyl chloride):[3]

HCOONa + C6H5C(O)F → FC(O)H + C6H5COONa

Structure

The molecule is planar; C-O and C-F distances are 1.18 and 1.34 A, respectively.[1]

Reactions

HC(O)F decomposes autocatalytically near room temperature to carbon monoxide and hydrogen fluoride:

HC(O)F → HF + CO

Because of the compound's sensitivity, reactions are conducted at low temperatures and samples are often stored over anhydrous alkali metal fluorides, e.g. potassium fluoride which absorbs HF.

Benzene (and other arenes) react with formyl fluoride in the presence of boron trifluoride to give benzaldehyde. In a related reaction, formyl chloride is implicated in Gattermann-Koch formylation reaction. The reaction of formyl fluoride/BF3 with perdeuteriobenzene (C6D6) exhibits a kinetic isotope effect of 2.68, similar to the isotope effect observed in Friedel-Crafts acetylation of benzene. Formylation of benzene with a mixture of CO and hexafluoroantimonic acid however, exhibits no isotope effect (C6H6 and C6D6 react at the same rate), indicating that this reaction involves a more reactive formylating agent, possibly CHO+.[3]

Formyl fluoride undergoes the reactions expected of an acyl halide: alcohols and carboxylic acids are converted to formate esters and mixed acid anhydrides, respectively.[4]

References

  1. ^ a b LeBlanc, O. H. Jr.; Laurie, V. W.; Gwinn, W. D. (1960). "Microwave Spectrum, Structure, and Dipole Moment of Formyl Fluoride". The Journal of Chemical Physics. 33 (2): 598–600. doi:10.1063/1.1731191.
  2. ^ Nesmejanow, A. N.; Kahn, E. J. (1934). "Über die unmittelbare Synthese von Säure-fluoriden aus Säuren und die Herstellung von Formylfluorid". Chemische Berichte. 67 (3): 370–373. doi:10.1002/cber.19340670303.
  3. ^ a b Olah, G. A.; Ohannesian, L.; Arvanaghi, M. (1987). "Formylating Agents". Chemical Reviews. 87 (4): 671–686. doi:10.1021/cr00080a001.
  4. ^ Olah, G. A.; Prakash, G. K. S.; Wang, Q.; Li, X. (2001). "Formyl Fluoride". In L. Paquette (ed.). Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289X.rf027.