Fluoroacetic acid
Names
Preferred IUPAC name
Fluoroacetic acid
Other names
2-Fluoroacetic acid
Monofluoroacetic acid
Monofluoroacetate[1]
Fluoroethanoic acid
Cymonic acid
Identifiers
3D model (JSmol)
3DMet
1739053
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.120 Edit this at Wikidata
EC Number
  • 205-631-7
25730
KEGG
RTECS number
  • AH5950000
UNII
UN number 2642
  • 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
  • FCC(O)=O
Properties
C2H3FO2
Molar mass 78.042 g·mol−1
Appearance White solid
Density 1.369
Melting point 35.2 °C (95.4 °F; 308.3 K)
Boiling point 165 °C (329 °F; 438 K)
Soluble in water and ethanol
Acidity (pKa) 2.586
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly toxic and corrosive
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS09: Environmental hazard
Danger
H300, H314, H400
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):
7 mg/kg (rat, oral)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fluoroacetic acid is a organofluorine compound with formula CH2FCO2H. It is a colorless solid that is noted for its relatively high toxicity.[3] The conjugate base, fluoroacetate occurs naturally in at least 40 plants in Australia, Brazil, and Africa. It is one of only five known organic fluorine-containing natural products.[4]

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.[5]

In contrast with monofluoroacetic acid, difluoroacetic acid and trifluoroacetic acid are far less toxic. Its pKa is 2.66, in contrast to 1.24 and 0.23 for the respective di- and trifluorinated acids.[6]

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.[7]

See also

References

Wikimedia Commons has media related to Fluoroacetic acid.
  1. ^ as anion of fluoroacetic acid
  2. ^ Fluoroacetic acid toxicity
  3. ^ 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.
  4. ^ K.K. Jason Chan; David O'Hagan (2012). The Rare Fluorinated Natural Products and Biotechnological Prospects for Fluorine Enzymology. Methods in Enzymology. Vol. 516. pp. 219–235. doi:10.1016/B978-0-12-394291-3.00003-4. ISBN 9780123942913. PMID 23034231.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
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