Chemistry:Fluoroacetic acid
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Fluoroacetic acid | |||
| Other names | |||
| Identifiers | |||
3D model (JSmol)
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| 3DMet | |||
| 1739053 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| EC Number |
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| 25730 | |||
| KEGG | |||
PubChem CID
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| RTECS number |
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| UNII | |||
| UN number | 2642 | ||
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| 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 | |||
| Main hazards | Highly toxic and corrosive | ||
| GHS pictograms |   
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| GHS Signal word | Danger | ||
| H300, H314, H400 | |||
| P260, P264, P270, P273, P280, P301+310, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P330, P363, P391, P405, P501 | |||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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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). | |||
| Infobox references | |||
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
- ↑ as anion of fluoroacetic acid
- ↑ Fluoroacetic acid toxicity
- ↑ 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. Methods in Enzymology. 516. pp. 219–235. doi:10.1016/B978-0-12-394291-3.00003-4. ISBN 9780123942913.
- ↑ 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. PMID 33513303.
- ↑ G. Siegemund; W. Schwertfeger; A. Feiring; B. Smart; F. Behr; H. Vogel; B. McKusick. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349.
- ↑ 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. https://www.marketwatch.com/press-release/global-fluoroacetic-acid-market-share-size-2021-consumption-analysis-by-applications-future-demand-top-leading-players-competitive-situation-and-emerging-trends-and-forecast-to-2027-2021-10-25.
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