Fluoroacetic acid

Fluoroacetic acid is a organofluorine compound with formula CH2FCO2H. It is a colorless solid that is noted for its relatively high toxicity.[1] In contrast with monofluoroacetic 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 trifluorinated acids.[2] The conjugate base, fluoroacetate occurs naturally in at least 40 plants in Australia, Brazil, and Africa. It is one of only five known organic fluorine-containing natural products.[3]

Fluoroacetic acid
Names
Preferred IUPAC name
Fluoroacetic acid
Other names
2-Fluoroacetic acid
Monofluoroacetic acid
Monofluoroacetate
Fluoroethanoic acid
Cymonic acid
Identifiers
3D model (JSmol)
3DMet
1739053
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.120
EC Number
  • 205-631-7
25730
KEGG
RTECS number
  • AH5950000
UNII
UN number 2642
Properties
C2H3FO2
Molar mass 78.042 g·mol−1
Appearance White solid
Density 1.369
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
GHS pictograms
GHS Signal word Danger
H300, H314, H400
P260, P264, P270, P273, P280, P301+310, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P330, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. 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.
  2. 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.
  3. K.K. Jason Chan; David O'Hagan (2012). "The Rare Fluorinated Natural Products and Biotechnological Prospects for Fluorine Enzymology". Methods in Enzymology. 516: 219–235. doi:10.1016/B978-0-12-394291-3.00003-4. ISBN 9780123942913. PMID 23034231.
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