 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name Fluoroacetic acid | |
Other names
| |
| Identifiers | |
| |
3D model (JSmol) | |
| 1739053 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.005.120 |
| EC Number |
|
| 25730 | |
| KEGG | |
| RTECS number |
|
| UNII | |
| UN number | 2642 |
| |
| |
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Fluoroacetic acid is aorganofluorine compound with thechemical formulaFCH2CO2H. It is a colorless solid that is noted for its relatively high toxicity.[1] Theconjugate base,fluoroacetate occursnaturally in at least 40plants inAustralia,Brazil, andAfrica. It is one of only five knownorganofluorine-containing natural products.[2]
Fluoroacetic acid is a harmfulmetabolite of somefluorine-containingdrugs (median lethal dose, LD50 = 10 mg/kg inhumans). The most common metabolic sources of fluoroacetic acid arefluoroamines andfluoroethers. Fluoroacetic acid can disrupt theKrebs cycle.[3] Themetabolite of fluoroacetic acid isFluorocitric acid and is verytoxic because it is not processable usingaconitase in the Krebs cycle (where fluorocitrate takes place ofcitrate as thesubstrate). Theenzyme isinhibited and the cycle stops working.[4]
In contrast with fluoroacetic acid,difluoroacetic acid andtrifluoroacetic acid are far less toxic. ItspKa is 2.66[contradictory], in contrast to 1.24 and 0.23 for the respective di- and trifluoroacetic acid.[5]
Fluoroacetic acid is used to manufacturepesticides especiallyrodenticides such assodium fluoroacetate (compound 1080). The overall market is projected to rise at a considerable rate during the forecast period, 2021 to 2027.[6]
