- Formyl fluoride
Chembox new
Name = Formyl fluoride
ImageFileL1 = Formyl-fluoride-2D.png
ImageNameL1 = Formyl fluoride
ImageFileR1 = Formyl-fluoride-3D-vdW.png
ImageNameR1 = Formyl fluoride
IUPACName = Formyl fluoride
OtherNames = Formic acid fluoride
Section1 = Chembox Identifiers
SMILES = FC(H)=O
CASNo = 1493-02-3
Section2 = Chembox Properties
Formula = CHFO
MolarMass = 48.02 g/mol
Appearance = Colourless gas
Density =
Solubility = decomposes
Solvent = other solvents
SolubleOther = chlorocarbons,Freon s
MeltingPt = -142 °C
BoilingPt = –29 °C
Section3 = Chembox Structure
Dipole = 2.02 DLeBlanc, Jr., O. H.; Laurie, V. W.; Gwinn, W. D. “Microwave Spectrum, Structure, and Dipole Moment of Formyl Fluoride” The Journal of Chemical Physics 1960, volume 33, pp. 598-600.]
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = toxic
Section8 = Chembox Related
OtherCpds =Formic acid Hydrogen fluoride Carbonyl fluoride Formyl fluoride is the
organic compound with the formula FC(O)H. It is the only verifiedacyl halide offormic acid .Preparation
FC(O)H was first reported in the 1934. [Nesmejanow, A. N.; Kahn, E. J. “Über die unmittelbare Synthese von Säure-fluoriden aus Säuren und die Herstellung von Formylfluorid” Chemische Berichte. 1934, volume 67, page 370-373. DOI: 10.1002/cber.19340670303] Among the many preparations, a typical one involves the reaction of
sodium formate with benzoyl fluoride (generated in situ from KHF2 andbenzoyl chloride ):Olah, G. A.; Ohannesian, L.; Arvanaghi, M, ”Formylating Agents” Chemical Reviews, 1987, volume 87, pp 671 - 686. DOI: 10.1021/cr00080a001]:NaOC(O)H + C6H5C(O)F → FC(O)H + C6H5CO2Na
tructure
The molecule is planar; C-O and C-F distances are 1.18 and 1.34 A, respectively.
Reactions
HC(O)F decomposes autocatalytically near room temperature to
carbon monoxide andhydrogen 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.KF which absorbs HF.Benzene (and otherarene s) react with formyl fluoride in the presence ofboron trifluoride to givebenzaldehyde . In a related reaction, formyl chloride is implicated in Gattermann-Koch formylation reaction. The reaction of formyl fluoride/BF3 with perdeuteriobenzene (C6D6) exhibits akinetic isotope effect of 2.68, similar to the isotope effect observed inFriedel-Crafts acetylation of benzene. Formylation of benzene with a mixture of CO andhexafluoroantinomic 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+.Formyl fluoride undergoes the reactions expected of an acyl halide:
alcohol s andcarboxylic acids are converted to formateester s and mixedacid anhydride s, respectively. [Olah, G. A.; Prakash, G. K. S.; Wang, Q.; Li, X. "Formyl Fluoride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.]References
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