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Trifluoroacetic acid

For the abbreviation TFA, or another perfluoro compound, see TFA (disambiguation) and Trifluoroacetone.
On Wikipedia, TFA refers to Today's featured article.

Trifluoroacetic acid
Names
Preferred IUPAC name
Trifluoroacetic acid
Other names
2,2,2-Trifluoroacetic acid
2,2,2-Trifluoroethanoic acid
Perfluoroacetic acid
Trifluoroethanoic acid
TFA
Identifiers
3D model (JSmol)
742035
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.846 Edit this at Wikidata
2729
RTECS number
  • AJ9625000
UNII
  • InChI=1S/C2HF3O2/c3-2(4,5)1(6)7/h(H,6,7) checkY
    Key: DTQVDTLACAAQTR-UHFFFAOYSA-N checkY
  • InChI=1/C2HF3O2/c3-2(4,5)1(6)7/h(H,6,7)
    Key: DTQVDTLACAAQTR-UHFFFAOYAP
  • FC(F)(F)C(=O)O
Properties
C2HF3O2
Molar mass 114.023 g·mol−1
Appearance colorless liquid
Odor Pungent/Vinegar
Density 1.489 g/cm3, 20 °C
Melting point −15.4 °C (4.3 °F; 257.8 K)
Boiling point 72.4 °C (162.3 °F; 345.5 K)
miscible
Vapor pressure 0.0117 bar (1.17 kPa) at 20 °C[1]
Acidity (pKa) 0.52 [2]
Conjugate base trifluoroacetate
-43.3·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly corrosive
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H314, H332, H412
P260, P261, P264, P271, P273, P280, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P363, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
1
Safety data sheet (SDS) External MSDS
Related compounds
Related perfluorinated acids
 Heptafluorobutyric acid
Perfluorooctanoic acid
Perfluorononanoic acid
Related compounds
 Acetic acid
Trichloroacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Trifluoroacetic acid (TFA) is a synthetic organofluorine compound with the chemical formula CF3CO2H. It is a haloacetic acid, with all three of the acetyl group's hydrogen atoms replaced by fluorine atoms. It is a colorless liquid with a vinegar-like odor. TFA is a stronger acid than acetic acid, having an acid ionisation constant, Ka, that is approximately 34,000 times higher,[3] as the highly electronegative fluorine atoms and consequent electron-withdrawing nature of the trifluoromethyl group weakens the oxygen-hydrogen bond (allowing for greater acidity) and stabilises the anionic conjugate base. TFA is commonly used in organic chemistry for various purposes.

  1. ^ Kreglewski, A. (1962). "Trifluoroacetic acid". Welcome to the NIST WebBook. 10 (11–12): 629–633. Retrieved 1 March 2020.
  2. ^ W. M. Haynes.; David R. Lide; Thomas J. Bruno, eds. (2016–2017). CRC Handbook of Chemistry and Physics. CRC Press. pp. 954–963. ISBN 978-1-4987-5429-3.
  3. ^ Note: Calculated from the ratio of the Ka values for TFA (pKa = 0.23) and acetic acid (pKa = 4.76)
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