|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||100.04 g/mol|
|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 ethanol||Miscible|
|Acidity (pKa)||12.46±0.10 Most Acidic Temp: 25 °C|
|Viscosity||0.9 cSt @ 37.78 °C|
Std enthalpy of
Std enthalpy of
|R-phrases (outdated)||R10, R20/21/22, R36/38, R62|
|S-phrases (outdated)||S16, S36/37/39, S45|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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. Thus, TFE forms stable complexes also with heterocycles (e.g. THF or pyridine) through hydrogen bonding.
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.
Trifluoroethanol is used as a solvent in organic chemistry. Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFE. It can also be used as a protein denaturant. In biology TFE is used as a co-solvent in protein folding studies with NMR spectroscopy: this solvent can effectively solubilize both peptides and proteins. Depending upon its concentration, TFE can strongly affect the three-dimensional structure of proteins.
Industrially trifluoroethanol is employed as a solvent for nylon as well as in applications of the pharmaceutical field.
Trifluoroethanol, specifically 2,2,2 trifluoroethanol is also used in biochemistry as an inhibitor to study enzymes. It competitively inhibits alcohol dehydrogenase for example.
Oxidation of trifluoroethanol yields trifluoroacetaldehyde or trifluoroacetic acid. It also serves as a source of the trifluoromethyl group for various chemical reactions (Still-Gennari modification of HWE reaction).
2,2,2-trifluoro-1-vinyloxyethane, 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.
- Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, 2007.
- Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. (2004). "Fluorinated Alcohols: A New Medium for Selective and Clean Reaction". Synlett (Review) (1): 18–29. doi:10.1055/s-2003-44973.
- Shuklov, Ivan A.; Dubrovina, Natalia V.; Börner, Armin (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". Synthesis (Review). 2007 (19): 2925–2943. doi:10.1055/s-2007-983902.
- Kabayadi S. Ravikumar; Venkitasamy Kesavan; Benoit Crousse; Danièle Bonnet-Delpon; Jean-Pierre Bégué (2003). "Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyle Phenyl Sulfoxide". Organic Syntheses. 80: 184.
- Taber, Richard L. (1998). "Wiley Online Library". Biochemical Education. 26 (3): 239–242. doi:10.1016/s0307-4412(98)00073-9.
- Sciencelab MSDS
- Fischer Scientific MSDS
- Halocarbon Fluorochemicals
- United States Patent number 4,647,706 "Process for the synthesis of 2,2,2-Trifluoroethanol and 1,1,1,3,3,3-Hexafluoroisopropanol"