Rahul Sharma (Editor)

2,2,2 Trifluoroethanol

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Density  1.39 g/cm³
Formula  C2H3F3O
Appearance  Colorless liquid
Boiling point  78 °C
Molar mass  100.04 g/mol
2,2,2-Trifluoroethanol 222Trifluoroethanol7589813CNMR
Related compounds  1,1,1-Trifluoroethane Trifluoroacetic acid

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.

Contents

2,2,2-Trifluoroethanol 222Trifluoroethanol758981HNMR

Synthesis

2,2,2-Trifluoroethanol httpsuploadwikimediaorgwikipediacommonsthu

Trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acid chloride.

2,2,2-Trifluoroethanol 1PHENYL222TRIFLUOROETHANOL C8H7F3O ChemSpider

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.

Uses

2,2,2-Trifluoroethanol 222trifluoroethanol Critically Evaluated Thermophysical

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.

Reactions

2,2,2-Trifluoroethanol 222Trifluoroethanol C2H3F3O ChemSpider

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-Trifluoroethanol Anesthetic Structure Database 222Trifluoroethanol

2,2,2-trifluoro-1-vinyloxyethane, an inhaled drug introduced clinically under the tradename Fluoromar, features a vinylether of trifluorethanol. This species was prepared by the reaction of trifluoroethanol with acetylene.

Safety

2,2,2-Trifluoroethanol 222Trifluoroethanol SigmaAldrich

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.

References

2,2,2-Trifluoroethanol Wikipedia


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