Fluoroacetic acid

Fluoroacetic acid is an organofluorine compound with the chemical formula FCH₂CO₂H. 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 five known organofluorine-containing natural products.

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 pK_a is approx. 2.6, in contrast to 1.3 and 0.5 for the respective di- and trifluoroacetic acid.

Fluoroacetic acid is used to manufacture pesticides especially rodenticides such as sodium fluoroacetate (compound 1080). The overall market is projected to rise at a considerable rate during the forecast period, 2021 to 2027.