Names | |
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Preferred IUPAC name
Fluoroacetic acid | |
Other names
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Identifiers | |
3D model (JSmol)
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3DMet | |
1739053 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.005.120 |
EC Number |
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25730 | |
KEGG | |
PubChem CID
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RTECS number |
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UNII | |
UN number | 2642 |
CompTox Dashboard (EPA)
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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 |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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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)
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7 mg/kg (rat, oral) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
Toxicity[edit]
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]
In contrast with fluoroacetic 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 trifluoroacetic acid.[4]
Uses[edit]
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.[5]
See also[edit]
- Haloacetic acids
- Difluoroacetic acid
- Trifluoroacetic acid
- Chloroacetic acid
- Bromoacetic acid
- Iodoacetic acid
- Fluoroacetamide
References[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. 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.
- ^ 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.