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Fluoroacetic acid
	; Carbon, C Hydrogen, H Oxygen, O Fluorine, F
Names
	Preferred IUPAC name Fluoroacetic acid
	Other names 2-Fluoroacetic acid; Cymonic acid; Fluoroethanoic acid; Monofluoroacetic acid;
Identifiers
CAS Number	144-49-0 ;
3D model (JSmol)	Interactive image;
3DMet	B00905;
Beilstein Reference	1739053
ChEBI	CHEBI:30775;
ChEMBL	ChEMBL509273;
ChemSpider	10205670;
ECHA InfoCard	100.005.120
EC Number	205-631-7;
Gmelin Reference	25730
KEGG	C06108;
PubChem CID	5237;
RTECS number	AH5950000;
UNII	AP1JV9U41M ;
UN number	2642
CompTox Dashboard (EPA)	DTXSID0041981 ;
	InChI InChI=1S/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5) Key: QEWYKACRFQMRMB-UHFFFAOYSA-N; InChI=1/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5) Key: QEWYKACRFQMRMB-UHFFFAOYAF;
	SMILES FCC(O)=O;
Properties
Chemical formula	FCH2CO2H
Molar mass	78.042 g·mol−1
Appearance	White solid
Density	1.369 g/cm3
Melting point	35.2 °C (95.4 °F; 308.3 K)
Boiling point	165 °C (329 °F; 438 K)
Solubility in water	Soluble in water and ethanol
Acidity (pKa)	2.586[contradictory]
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Highly toxic and corrosive
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H314, H400
Precautionary statements	P260, P264, P270, P273, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P391, P405, P501
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	7 mg/kg (rat, oral)
Related compounds
Related compounds	Difluoroacetic acid; Trifluoroacetic acid; Chloroacetic acid; Bromoacetic acid; Iodoacetic acid; Acetic acid; Haloacetic acids; Fluoroacetamide; Sodium fluoroacetate;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Fluoroacetic acid is a organofluorine compound with the chemical formula F C H₂CO₂H. It is a colorless solid that is noted for its relatively high toxicity.^[1] The conjugate base, fluoroacetate occurs naturally in at least 40 plants in Australia, Brazil, and Africa. It is one of only five known organofluorine-containing natural products.^[2]

Toxicity

Fluoroacetic acid is a harmful metabolite of some fluorine-containing drugs (median lethal dose, LD₅₀ = 10 mg/kg in humans). The most common metabolic sources of fluoroacetic acid are fluoroamines and fluoroethers. Fluoroacetic acid can disrupt the Krebs cycle.^[3]The metabolite of fluoroacetic acid is Fluorocitric acid and is very toxic because it is not processable using aconitase in the Krebs cycle (where fluorocitrate takes place of citrate as the substrate). The enzyme is inhibited and the cycle stops working.^[4]

In contrast with fluoroacetic acid, difluoroacetic acid and trifluoroacetic acid are far less toxic. Its pK_a is 2.66^{[contradictory]}, in contrast to 1.24 and 0.23 for the respective di- and trifluoroacetic acid.^[5]

Uses

Fluoroacetic acid is used to manufacture pesticides especially rodenticides (see sodium fluoroacetate). The overall market is projected to rise at a considerable rate during the forecast period, 2021 to 2027.^[6]

References

^ Timperley, Christopher M. (2000). "Highly-toxic fluorine compounds". Fluorine Chemistry at the Millennium. pp. 499–538. doi:10.1016/B978-008043405-6/50040-2. ISBN 9780080434056.
^ K.K. Jason Chan; David O'Hagan (2012). "The Rare Fluorinated Natural Products and Biotechnological Prospects for Fluorine Enzymology". Natural Product Biosynthesis by Microorganisms and Plants, Part B. Methods in Enzymology. Vol. 516. pp. 219–235. doi:10.1016/B978-0-12-394291-3.00003-4. ISBN 9780123942913. PMID 23034231.
^ Kyzer, Jillian L.; Martens, Marvin (15 March 2021). "Metabolism and Toxicity of Fluorine Compounds". Chemical Research in Toxicology. 34 (3): 678–680. doi:10.1021/acs.chemrestox.0c00439. PMC 8023797. PMID 33513303.
^ Horák, J.; Linhart, I.; Klusoň, P. (2004). Úvod do toxikologie a ekologie pro chemiky (in Czech) (1st ed.). Prague: VŠCHT v Praze. ISBN 80-7080-548-X.
^ G. Siegemund; W. Schwertfeger; A. Feiring; B. Smart; F. Behr; H. Vogel; B. McKusick. "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349. ISBN 978-3527306732.
^ Industry Research (October 25, 2021). "Global Fluoroacetic Acid Market Share, Size 2021: Consumption Analysis By Applications, Future Demand, Top Leading Players, Competitive Situation and Emerging Trends, and Forecast to 2027". MarketWatch. Archived from the original on 2022-01-05. Retrieved 5 January 2022.