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Trifluoroethanol serves as a solvent and a raw material in organic chemistry and biology. TFE is a solvent of choice for hydrogen peroxide-mediated oxidations of sulfides. Trifluoroethanol acts as a protein denaturant. It is used in the manufacture of certain pharmaceuticals and drug substances. The drug fluromer, which is 2,2,2-trifluoro-1-vinyloxyethane, is the vinyl ether of trifluorethanol. It is an effective solvent for peptides and proteins, and used for NMR-based protein folding studies, and in the manufacture of nylon. As a source of the trifluoromethyl group, it is employed in several organic reactions, for example in Still-Gennari modification of Horner-Wadsworth-Emmons reaction (HWE) reaction.
Useful ionizing solvent, see: Tetrahedron Lett., 2335 (1974), and references therein. Good solvent for oligopeptides with potential as a cosolvent along with proton acceptors such as DMF for peptide coupling reactions: Tetrahedron Lett., 33, 7007 (1992). Compare 1,1,1,3,3,3-Hexafluoro-2-propanol, A12747.
Effective solvent for uncatalyzed epoxidations of alkenes with hydrogen peroxide (caution! 60%): Synlett, 248 (2001). For a review of fluorinated alcohols as solvents for selective and clean reactions, see: Synlett, 18 (2004).
Trifluoroethyl esters have also found use as active esters in peptide coupling; see, for example: J. Chem. Soc., Perkin 1, 2867 (1996).
Reacts with triphenylphosphine dibromide to give the bis(trifluoroethoxy)phosphorane, which converts alcohols to trifluoroethyl ethers, carboxylic acids to trifluoroethyl esters and aldehydes to bis(trifluoroethyl) acetals: J. Org. Chem., 45, 5052 (1980).
The stereodirecting effect of the MEM group (see 2-Methoxyethoxymethyl chloride, L01050) has been exploited by Percy et al in the formation of a new fluorine-containing acyl anion equivalent: Tetrahedron, 51, 9201 (1995):
Claisen or Wittig rearrangements of the derived difluoroallyl alcohols can be used in routes to molecules containing a CF2 group: Tetrahedron, 51, 11327 (1995); J. Org. Chem., 61, 166 (1996), or to monofluorinated vinylic compounds: Tetrahedron Lett., 37, 5183 (1996).
Bava, Y. B.; Martínez, Y. B.; Betancourt, A. M.; Erben, M. F.; Filho, R. L. C.; Védova, C. O. D.; Romano, R. M. Ionic Fragmentation Mechanisms of 2, 2, 2-Trifluoroethanol Following Excitation with Synchrotron Radiation. Inorg. Chim. Acta 2015, 431, 242-247.
Hazard Statements: H226-H301-H318-H331-H360F-H373
Flammable liquid and vapour. Toxic if swallowed. Causes serious eye damage. Toxic if inhaled. May damage fertility. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P201-P202-P210-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P281-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-P310-P311-P330-P370+P378q-P501c
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Use personal protective equipment as required. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention. Call a POISON CENTER or doctor/physician. Rinse mouth. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant