Fluoroacetic acid is an organofluorine compound with the chemical formula . It is a colorless solid that is noted for its relatively high toxicity. The conjugate base, fluoroacetate occurs naturally in at least 40 plants in Australia, Brazil, and Africa. It is one of only about twenty known organofluorine-containing natural products.
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. The metabolite of fluoroacetic acid is fluorocitric acid, which 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.
In contrast with fluoroacetic acid, difluoroacetic acid and trifluoroacetic acid are far less toxic. Its pKa is approx. 2.6, in contrast to 1.3 and 0.5 for the respective di- and trifluoroacetic acid.
Manufacture and uses The main use of fluoroacetic acid is as a pesticide, especially rodenticides such as sodium fluoroacetate (compound 1080), which are salts of the acid. The overall market is projected to rise at a considerable rate during the forecast period, 2021 to 2027. Sodium fluoroacetate is manufactured by treating sodium chloroacetate with potassium fluoride and the parent acid can be obtained by neutralization and distillation.
See also Chloroacetic acid Fluorocitric acid Fluorooleic acid
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