Fluoroacetic acid

Chemical compound From Wikipedia, the free encyclopedia

Fluoroacetic acid is an 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]

Quick facts Names, Identifiers ...
Fluoroacetic acid
  Carbon, C
  Hydrogen, H
  Oxygen, O
  Fluorine, F
Names
Preferred IUPAC name
Fluoroacetic acid
Other names
  • 2-Fluoroacetic acid
  • Cymonic acid
  • Fluoroethanoic acid
  • Monofluoroacetic acid
Identifiers
3D model (JSmol)
1739053
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.120 Edit this at Wikidata
EC Number
  • 205-631-7
25730
KEGG
RTECS number
  • AH5950000
UNII
UN number 2642
  • InChI=1S/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5)
    Key: QEWYKACRFQMRMB-UHFFFAOYSA-N
  • InChI=1/C2H3FO2/c3-1-2(4)5/h1H2,(H,4,5)
    Key: QEWYKACRFQMRMB-UHFFFAOYAF
  • FCC(O)=O
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) 2.6
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly toxic and corrosive
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS09: Environmental hazard
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):
7 mg/kg (rat, oral)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[3] 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.[4]

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.[5]

Uses

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.[6]

See also

References

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