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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. Thus, TFE form stable complexes also with heterocycles (e.g. THF or pyridine) through hydrogen bonding. Additional recommended knowledge
SynthesisTrifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acid chloride.[1] TFE can also be prepare 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.[citation needed] As a co-catalyst for this conversion tertiary aliphatic amines like triethylamine are commonly employed. As a solventTrifluoroethanol is used as a solvent in organic chemistry [2], [3]. Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFE.[4] 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. ReactionsOxidation 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 Fluromar, features a vinylether of trifluorethanol. This species was prepared by the reaction of trifluoroethanol with acetylene.[1]
References
Categories: Organofluorides | Halogenated solvents | Alcohols |
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "2,2,2-Trifluoroethanol". A list of authors is available in Wikipedia. |