TFA is the precursor to many other fluorinated compounds such as
trifluoroacetic anhydride,
trifluoroperacetic acid, and
2,2,2-trifluoroethanol.[4] It is a
reagent used in
organic synthesis because of a combination of convenient properties: volatility, solubility in organic solvents, and its strength as an acid.[7] TFA is also less oxidizing than
sulfuric acid but more readily available in anhydrous form than many other acids. One complication to its use is that TFA forms an
azeotrope with water (b. p. 105 °C).
At a low concentration, TFA is used as an ion pairing agent in
liquid chromatography (HPLC) of organic compounds, particularly
peptides and small
proteins. TFA is a versatile solvent for
NMR spectroscopy (for materials stable in acid). It is also used as a calibrant in mass spectrometry.[10]
TFA is used to produce trifluoroacetate salts.[11]
Safety
Trifluoroacetic acid is a corrosive strong acid[12] but it does not pose the hazards associated with
hydrofluoric acid because the
carbon-fluorine bond is not
labile. TFA is harmful when inhaled, causes severe skin burns and is toxic for aquatic organisms even at low concentrations.
TFA's reaction with bases and metals, especially
light metals, is strongly exothermic. The reaction with
lithium aluminium hydride (LAH) results in an explosion.[13]
TFA is a metabolic breakdown product of the volatile anaesthetic agent
halothane. It is thought to be responsible for halothane induced
hepatitis.[14]
Trifluoroacetic acid
degrades very slowly in the environment. Median concentrations of a few micrograms per liter have been found in beer and tea.[16] Sea water contains about 200 ng of TFA per liter.[17][18][19] No biodegradation mechanism for the compound is known in water,[20] although
biotransformation apparently
decarboxylates the acid to
fluoroform.[21]
^Lundt, Behrend F.; Johansen, Nils L.; Vølund, Aage; Markussen, Jan (1978). "Removal of t-Butyl and t-Butoxycarbonyl Protecting Groups with Trifluoroacetic acid". International Journal of Peptide and Protein Research. 12 (5): 258–268.
doi:
10.1111/j.1399-3011.1978.tb02896.x.
PMID744685.
^Andrew B. Hughes (2011). "1. Protection Reactions". In Vommina V. Sureshbabu; Narasimhamurthy Narendra (eds.). Amino Acids, Peptides and Proteins in Organic Chemistry: Protection Reactions, Medicinal Chemistry, Combinatorial Synthesis. Vol. 4. pp. 1–97.
doi:
10.1002/9783527631827.ch1.
ISBN978-3-527-63182-7.
^Stout, Steven J.; Dacunha, Adrian R. (1989). "Tuning and calibration in thermospray liquid chromatography/mass spectrometry using trifluoroacetic acid cluster ions". Analytical Chemistry. 61 (18): 2126.
doi:
10.1021/ac00193a027.
^O. Castano; A. Cavallaro; A. Palau; J. C. Gonzalez; M. Rossell; T. Puig; F. Sandiumenge; N. Mestres; S. Pinol; A. Pomar & X. Obradors (2003). "High quality YBa2Cu3O7 thin films grown by trifluoroacetates metal-organic deposition". Superconductor Science and Technology. 16 (1): 45–53.
Bibcode:
2003SuScT..16...45C.
doi:
10.1088/0953-2048/16/1/309.
S2CID250765145.
^Safety data sheet for
Trifluoroacetic acid (PDF) from EMD Millipore, revision date 10/27/2014.
^"Halothane", LiverTox: Clinical and Research Information on Drug-Induced Liver Injury, Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases, 2012,
PMID31643481, retrieved 15 July 2021