Formyl fluoride

Formyl fluoride
Formyl fluoride	Formyl fluoride
Names
	Preferred IUPAC name Formyl fluoride
	Other names Formic acid fluoride; Methanoyl fluoride
Identifiers
CAS Number	1493-02-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	14424 ;
PubChem CID	15153;
UNII	0UY0U66165 ;
CompTox Dashboard (EPA)	DTXSID6073946 ;
	InChI InChI=1S/CHFO/c2-1-3/h1H Key: NHGVZTMBVDFPHJ-UHFFFAOYSA-N ; InChI=1/CHFO/c2-1-3/h1H Key: NHGVZTMBVDFPHJ-UHFFFAOYAX;
	SMILES FC=O;
Properties
Chemical formula	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)
Solubility in water	Decomposes
Solubility in other solvents	Chlorocarbons,; Freons
Structure
Dipole moment	2.02 D[1]
Hazards
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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	Infobox references

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

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.
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.
Olah, G. A.; Ohannesian, L.; Arvanaghi, M. (1987). "Formylating Agents". Chemical Reviews. 87 (4): 671–686. doi:10.1021/cr00080a001.
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.

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[LeB-1] 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.

[Olah-3] 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.