Fluoroacetic acid is a organofluorine compound with the chemical formula FCH2CO2H. 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]
| |
 | |
| Names | |
|---|---|
| Preferred IUPAC name
Fluoroacetic acid | |
Other names
| |
| Identifiers | |
3D model (JSmol)
|
|
| 3DMet | |
| 1739053 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.005.120 |
| EC Number |
|
| 25730 | |
| KEGG | |
PubChem CID
|
|
| RTECS number |
|
| UNII | |
| UN number | 2642 |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| 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) |
| 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: | |
  
| |
| 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): | |
LD50 (median dose)
|
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).
| |
Toxicity
editFluoroacetic 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
editFluoroacetic 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]
See also
editReferences
edit
- ^ 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.