 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name 2,2,2-Trifluoroethan-1-ol | |
| Other names 2,2,2-Trifluoroethanol | |
| Identifiers | |
| |
3D model (JSmol) | |
| 1733203 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| DrugBank |
|
| ECHA InfoCard | 100.000.831 |
| EC Number |
|
| 2532 | |
| UNII | |
| |
| |
| Properties | |
| 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) |
| Miscible | |
| Solubility inethanol | Miscible |
| Acidity (pKa) | 12.46±0.10 Most Acidic Temp: 25 °C |
| Viscosity | 0.9 cSt @ 37.78 °C |
| Thermochemistry | |
Std enthalpy of combustion(ΔcH⦵298) | −886.6 kJ/mol |
| Hazards | |
| GHS labelling: | |
     | |
| Danger | |
| H226,H301,H312,H315,H318,H331,H332,H335,H360,H373 | |
| 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) | |
| Related compounds | |
Relatedalcohols | Hexafluoro-2-propanol |
Related compounds | 1,1,1-Trifluoroethane Trifluoroacetic acid |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
2,2,2-Trifluoroethanol is the syntheticorganic compound with theformula CF3CH2OH. Also known asTFEA ortrifluoroethyl alcohol, this colourless, water-miscible liquid has a smell reminiscent ofethanol. Due to theelectronegativity of thetrifluoromethyl group, thisalcohol exhibits a stronger acidic character compared to ethanol.
Trifluoroethanol is produced industrially byhydrogenation or the hydride reduction of derivatives oftrifluoroacetic acid, such as the esters or acyl chloride.[1]
TFEA can also be prepared byhydrogenolysis of compounds of generic formula CF3−CHOH−OR (where R ishydrogen or analkyl group containing from one to eightcarbon atoms), in the presence of apalladium containingcatalyst deposited on activatedcharcoal.[citation needed] As a co-catalyst for this conversion tertiary aliphatic amines liketriethylamine are commonly employed.
Trifluoroethanol is used as a specializedsolvent in organic chemistry.[2][3] Oxidations of sulfur compounds usinghydrogen peroxide are effectively conducted in TFEA.[4]
It competitively inhibits alcohol dehydrogenase for example.[5]
TFEA forms complexes with Lewis bases such asTHF orpyridine throughhydrogen bonding, yielding 1:1 adducts.[6] It is classified as ahard Lewis acid and its acceptor properties are discussed in theECW model yielding EA = 2.07 and CA = 1.06.
TFEA can be used inbiochemical experiments to stabilizealpha helix.[7][8] There are also stablebeta sheets in TFEA, suggesting that TFEA stabilizes the secondary structure the sequence has a preference for.[8]
Oxidation of trifluoroethanol yieldstrifluoroacetic acid. It also serves as a source of the trifluoroethoxy group for various chemical reactions (Still-Gennari modification ofHWE 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 withacetylene.[1]
Fluorester (2,2,2-trifluoroethyl methacrylate) is an ester ofmethacrylic acid and TFEA, which can be used as amonomer in specialty paints.[9]
Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes.[10] Research has shown it to be a testicular toxicant in rats and dogs.[11]
