2,2,2-trifluoroethanol 2,2,2-trifluoroethanol 2,2,2-trifluoroethanol is the organic compound with the formula cf3ch2oh. also known as tfe or trifluoroethyl alcohol, this colourless, water-miscible liquid has a smell reminiscent of ethanol. due to the electronegativity of the trifluoromethyl group, this alcohol exhibits a stronger acidic character compared to ethanol. 2,2,2-trifluoroethanol names preferred iupac name 2,2,2-trifluoroethan-1-ol other names 2,2,2-trifluoroethanol identifiers cas number 75-89-8 y 3d model (jsmol) interactive imageinteractive image beilstein reference 1733203 chebi chebi:42330 y chembl chembl116675 y chemspider 21106169 y drugbank db03226 y echa infocard 100.000.831 ec number 200-913-6 gmelin reference 2532 pubchem cid 6409 unii 8t8i76kyf1 y comptox dashboard (epa) dtxsid0021751 inchi inchi=1s/c2h3f3o/c3-2(4,5)1-6/h6h,1h2 nkey: rhqdfwaxviiebn-uhfffaoysa-n ninchi=1/c2h3f3o/c3-2(4,5)1-6/h6h,1h2key: rhqdfwaxviiebn-uhfffaoyah smiles occ(f)(f)ffc(f)(f)co properties chemical formula c2h3f3o molar mass 100.04 g/mol appearance colorless liquid density 1.325±0.06 g/ml @ 20 °c, 760 torr liquid melting point −43.5 °c (−46.3 °f; 229.7 k) boiling point 74.0 °c (165.2 °f; 347.1 k) solubility in water miscible solubility in ethanol miscible acidity (pka) 12.46±0.10 most acidic temp: 25 °c viscosity 0.9 cst @ 37.78 °c thermochemistry std molarentropy (s⦵298) ? j.k−1.mol−1 std enthalpy offormation (δfh⦵298) ? kj/mol std enthalpy ofcombustion (δch⦵298) -886.6 kj/mol hazards ghs labelling: pictograms signal word danger hazard statements h226, h301, h312, h315, h318, h331, h332, h335, h360, h373 precautionary statements p201, p202, p210, p233, p240, p241, p242, p243, p260, p261, p264, p270, p271, p280, p281, p301+p310, p302+p352, p303+p361+p353, p304+p312, p304+p340, p305+p351+p338, p308+p313, p310, p311, p312, p314, p321, p322, p330, p332+p313, p362, p363, p370+p378, p403+p233, p403+p235, p405, p501 nfpa 704 (fire diamond) 2 3 1 related compounds related alcohols hexafluoro-2-propanol related compounds 1,1,1-trifluoroethane trifluoroacetic acid except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). n verify (what is yn ?) infobox references synthesis trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acyl chloride. tfe can also be prepared by hydrogenolysis of compounds of generic formula cf3−choh−or (where r is hydrogen or an alkyl group containing from one to eight carbon atoms), in the presence of a palladium containing catalyst deposited on activated charcoal. as a co-catalyst for this conversion tertiary aliphatic amines like triethylamine are commonly employed. properties trifluoroethanol is used as a specialized solvent in organic chemistry. oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in tfe. it competitively inhibits alcohol dehydrogenase for example. tfe forms complexes with lewis bases such as thf or pyridine through hydrogen bonding, yielding 1:1 adducts. it is classified as a hard lewis acid and its acceptor properties are discussed in the ecw model yielding ea = 2.07 and ca = 1.06. reactions oxidation of trifluoroethanol yields trifluoroacetic acid. it also serves as a source of the trifluoroethoxy group for various chemical reactions (still-gennari modification of hwe reaction). 2,2,2-trifluoroethyl vinyl ether, an inhaled drug introduced clinically under the tradename fluoromar, features a vinyl ether of trifluorethanol. this species was prepared by the reaction of trifluoroethanol with acetylene. safety trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes. research has shown it to be a testicular toxicant in rats and dogs.