Carbonyl fluoride

Carbonyl fluoride
Structure of carbonyl fluoride	Space-filling model of the carbonyl fluoride molecule
Names
	Preferred IUPAC name Carbonyl difluoride
	Other names Carbon difluoride oxide; Fluoromethanoyl fluoride; Fluorophosgene;
Identifiers
CAS Number	353-50-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	9246 ;
ECHA InfoCard	100.005.941
EC Number	206-534-2;
PubChem CID	9623;
RTECS number	FG6125000;
UNII	2NU89R5398 ;
UN number	2417
CompTox Dashboard (EPA)	DTXSID7059858 ;
	InChI InChI=1S/CF2O/c2-1(3)4 Key: IYRWEQXVUNLMAY-UHFFFAOYSA-N ; InChI=1/CF2O/c2-1(3)4 Key: IYRWEQXVUNLMAY-UHFFFAOYAE;
	SMILES FC(F)=O;
Properties
Chemical formula	COF2
Molar mass	66.007 g·mol−1
Appearance	Colorless gas
Odor	Pungent and very irritating
Density	2.698 g/L (gas), 1.139 g/cm3 (liquid at melting point)
Melting point	−111.26 °C (−168.27 °F; 161.89 K)
Boiling point	−84.57 °C (−120.23 °F; 188.58 K)
Solubility in water	Reacts
Vapor pressure	55.4 atm (20°C)
Structure
Molecular shape	C2v
Dipole moment	0.95 D
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Very toxic, reacts with water to release HF
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H290, H314, H330, H370
Precautionary statements	P234, P260, P264, P270, P271, P280, P284, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P311, P320, P321, P363, P390, P403+P233, P404, P405, P410+P403, P501
NFPA 704 (fire diamond)	4 0 2 W
Flash point	Non-flammable
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 2 ppm (5 mg/m3) ST 5 ppm (15 mg/m3)
IDLH (Immediate danger)	N.D.
Related compounds
Related compounds	Phosgene; Carbonyl bromide; Formyl fluoride; Thiocarbonyl chloride; Acetone; Urea; Carbonic acid;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Carbonyl fluoride is a chemical compound with the formula CO F₂. It is a carbon oxohalide. This gas, like its analog phosgene, is colourless and highly toxic. The molecule is planar with C_2v symmetry, bond lengths of 1.174 Å (C=O) and 1.312 Å (C–F), and an F–C–F bond angle of 108.0°.^[3]

Preparation

Carbonyl fluoride is produced from trifluoromethanol. The latter is produced in turn by protonation of in-situ generated trifluoromethoxide.^[4]

Of potential relevance to atmospheric chemistry, tetrafluoromethane hydrolyses to carbonyl fluoride:

CF₄ + H₂O → COF₂ + 2 HF

Carbonyl fluoride can also be prepared by reaction of phosgene with hydrogen fluoride as well as the fluorination of carbon monoxide, although the latter tends to result in over-fluorination to carbon tetrafluoride. The fluorination of carbon monoxide with silver difluoride is convenient:^[5]

CO + 2 AgF₂ → COF₂ + 2 AgF

Reactions

Carbonyl fluoride readily hydrolyzes to carbon dioxide and hydrogen fluoride:^[5]

COF₂ + H₂O → CO₂ + 2 HF

When produced in situ, carbonyl fluoride converts carboxylic acids to acyl fluorides:^[4]

CF₂O + RCO₂H → RCOF + HF + CO₂

Safety

Carbonyl fluoride is very toxic with a recommended exposure limit of 2 ppm as an 8-hour time weighted average and a 5 ppm as a short-term (15-minute average) exposure, where 1 ppm = 2.70 mg of carbonyl fluoride per 1 m³ of air.^[1]

References

^ ^a ^b "Carbonyl Fluoride". NIOSH Pocket Guide to Chemical Hazards. CDC Centers for Disease Control and Prevention. Retrieved 2013-09-10.
^ ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0108". National Institute for Occupational Safety and Health (NIOSH).
^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. pp. 304–305. doi:10.1016/C2009-0-30414-6. ISBN 978-0-08-037941-8.
^ ^a ^b Bonnefoy, Clémence; Gallego, Adrien; Delobel, Clément; Raynal, Betty; Decourt, Maxime; Chefdeville, Emmanuel; Hanquet, Gilles; Panossian, Armen; Leroux, Frédéric R.; Toulgoat, Fabien; Billard, Thierry (2024). "Unlocking the Power of Acyl Fluorides: A Comprehensive Guide to Synthesis and Properties". European Journal of Organic Chemistry. 27 (18) e202400142. doi:10.1002/ejoc.202400142.
^ ^a ^b M. W. Farlow; E. H. Man; C. W. Tullock (1960). "Carbonyl Fluoride". Inorganic Syntheses. Vol. 6. pp. 155–158. doi:10.1002/9780470132371.ch48. ISBN 9780470132371. {{cite book}}: ISBN / Date incompatibility (help)

[niosh-1] "Carbonyl Fluoride". NIOSH Pocket Guide to Chemical Hazards. CDC Centers for Disease Control and Prevention. Retrieved 2013-09-10.

[PGCH-2] NIOSH Pocket Guide to Chemical Hazards. "#0108". National Institute for Occupational Safety and Health (NIOSH).

[G&E-3] Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. pp. 304–305. doi:10.1016/C2009-0-30414-6. ISBN 978-0-08-037941-8.

[Bonnefoy-4] Bonnefoy, Clémence; Gallego, Adrien; Delobel, Clément; Raynal, Betty; Decourt, Maxime; Chefdeville, Emmanuel; Hanquet, Gilles; Panossian, Armen; Leroux, Frédéric R.; Toulgoat, Fabien; Billard, Thierry (2024). "Unlocking the Power of Acyl Fluorides: A Comprehensive Guide to Synthesis and Properties". European Journal of Organic Chemistry. 27 (18) e202400142. doi:10.1002/ejoc.202400142.

[IS-5] M. W. Farlow; E. H. Man; C. W. Tullock (1960). "Carbonyl Fluoride". Inorganic Syntheses. Vol. 6. pp. 155–158. doi:10.1002/9780470132371.ch48. ISBN 9780470132371. {{cite book}}: ISBN / Date incompatibility (help)

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