Fluoroacetic acid

Last updated
Fluoroacetic acid
Fluoroacetic Acid V.1.svg
Fluoroacetic-acid-from-xtal-3D-balls.png
   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
3D model (JSmol)
1739053
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.120 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-631-7
25730
KEGG
PubChem CID
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
FCH2CO2H
Molar mass 78.042 g·mol−1
AppearanceWhite 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)
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:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
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)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fluoroacetic acid is an organofluorine compound with the chemical formula F C H 2CO 2H. 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]

Contents

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 pKa 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 such as sodium fluoroacetate (compound 1080). The overall market is projected to rise at a considerable rate during the forecast period, 2021 to 2027. [6]

See also

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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   978-3-527-30673-2.
  6. ↑ 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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