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2,2,2-Trichloroethanol is used as a sedative or a hypnotic. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.
Maurice R. Eftink; James L. Zajicek; Camillo A. Ghiron. A Hydrophobic Quencher of Protein Fluorescence: 2,2,2-Trichloroethanol. Biochimica et Biophysica Acta (BBA) - Protein Structure. 1977, 491 473-481.
M. Perttilä. Vibrational spectra and normal coordinate analysis of 2,2,2-trichloroethanol and 2,2,2-trifluoroethanol. Spectrochimica Acta Part A: Molecular Spectroscopy. 1979, 35 585-592.
Carboxyl groups can be protected as their trichloroethyl esters e.g. by tosic acid-catalyzed esterification: Synthesis, 24 (1979), or DCC-DMAP: J. Am. Chem. Soc., 111, 669 (1989). For esterification of amino acids, using the active ester with 2-Hydroxypyridine, A14522, see: Synthesis, 24 (1979). Cleavage occurs with Zn in AcOH or an aqueous THF buffer under mild conditions: J. Am. Chem. Soc., 88, 852 (1966); Synthesis, 457 (1976); or with NaBH4 in DMF, catalyzed by Se: Synthesis, 693 (1989). See also Appendix 6.
Similarly, carbonyl compounds can be protected as their trichloroethyl acetals, stable to base, but readily cleaved under neutral aprotic conditions by Zn in ethyl acetate or THF: J. Org. Chem., 38, 554 (1973).
Reaction with POCl3 to give the phosphorodichloridate, followed by reaction with 3-Hydroxypropionitrile, L12570, gives 2-cyanoethyl 2,2,2-trichloroethyl phosphorochloridate, a valuable reagent, usually used without purification, for the phosphorylation of nucleosides: Synthesis, 831 (1980).
Hazard Statements: H302-H315-H318-H336
Harmful if swallowed. Causes skin irritation. Causes serious eye damage. May cause drowsiness or dizziness.
Precautionary Statements: P280-P305+P351+P338-P308+P313-P330-P501a
Wear protective gloves/protective clothing/eye protection/face protection. 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. Rinse mouth. Dispose of contents/container in accordance with local/regional/national/international regulations.