The combination of properties like solubility in most of the solvents, volatility, catalytic property, and strong acidity with non-oxidizing nature makes it a widely used reagent in organic synthesis. Trifluoroacetic acid is an important building block in the synthesis of pharmaceuticals, agrochemicals and performance products. It is a precursor to many fluorinated compounds, and widely used in peptide synthesis and other organic transformations involving deprotection of t-BOC group. TFA finds use as an ion pairing agent in liquid chromatography, as a solvent in NMR spectroscopy and as a calibrant in mass spectrometry.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
The combination of properties like solubility in most of the solvents, volatility, catalytic property, and strong acidity with non-oxidizing nature makes it a widely used reagent in organic synthesis. Trifluoroacetic acid is an important building block in the synthesis of pharmaceuticals, agrochemicals and performance products. It is a precursor to many fluorinated compounds, and widely used in peptide synthesis and other organic transformations involving deprotection of t-BOC group. TFA finds use as an ion pairing agent in liquid chromatography, as a solvent in NMR spectroscopy and as a calibrant in mass spectrometry.
Solubility
Miscible with ether, acetone, ethanol, benzene, hexane and carbon tetrachloride.
Notes
Trifluoroacetic acid (TFA) is a stable, hygroscopic, volatile and low-boiling organic acid. Storage in a cool place is recommended.
RUO – Research Use Only
General References:
- Strong organic acid, widely used in peptide synthesis to cleave N-Boc and t-butyl ester groups: Helv. Chim. Acta, 46, 870 (1963); see also Org. Synth. Coll., 9, 24, 268 (1998). For peptide reagents, see Appendix 6. For selective cleavage of Boc in the presence of Cbz (Z), using 70% TFA in water, see: Liebigs Ann. Chem., 749, 90 (1971). For selective cleavage of benzyl, benzhydryl and trityl ethers in the presence of ester functions, see: Synthesis, 249 (1983).
- Also catalyzes the cleavage of t-butyl groups from t-butylphenols, by reverse Friedel-Crafts reaction: Tetrahedron, 29, 4003 (1973). Similarly, hindered aryl ketones or aromatic carboxylic acids undergo deacylation: Synthesis, 979 (1985).
- Carrying out the Curtius rearrangement of acyl azides in TFA leads directly to the trifluoroacetamide, which can be readily hydrolyzed to the free amine: Synthesis, 38 (1983).
- With sodium nitrite, has been used for the cleavage of tosylhydrazones: Synthesis, 207 (1979); for nitrosation of anisole and derivatives, avoiding possible loss of the alkyl group: Acta Chem. Scand., 44, 152 (1990); for diazotization of weakly basic arylamines such as pentafluoroaniline or 3,5-dinitroaniline: Synthesis, 566 (1988); and in the presence of formamide, for deamination of arylamines: J. Chem. Soc., Perkin 1, 873 (1986).
- For use of TFA as a catalyst in the Meerwein-Ponndorf-Verley reduction, see Aluminum isopropoxide, 14007. For use in the modification of the reducing properties of borohydride, see Sodium borohydride, 13432. For use in the ionic hydrogenation, see Triethyl silane, A10320.
- López, S. E.; Salazar, J. Trifluoroacetic acid: Uses and recent applications in organic synthesis. J. Fluorine Chem. 2013, 156, 73-100.
- Natu, A. D.; Burde, A. S.; Limaye, R. A.; Paradkar, M. V. Acceleration of the Dakin reaction by trifluoroacetic acid. J. Chem. Res. 2014, 38 (6), 325-386.