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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. 2015, 16 (2), 322-330.
Scodeller, I.; Salvini, A.; Manca, G.; Ienco, A.; Luconi, L.; Oberhauser, W. 2,2,2-Trifluoroethanol-assisted imine hydrogenation by a Ru-monohydride. 2015, 431, 242-247.
Gefahrenhinweise (EU): H226-H301-H311-H332-H315-H318-H335
Flammable liquid and vapour. Toxic if swallowed. Toxic in contact with skin. Harmful if inhaled. Causes skin irritation. Causes serious eye damage. May cause respiratory irritation.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.