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Chemical compound From Wikipedia, the free encyclopedia
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.
Names | |
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Preferred IUPAC name
2,2,2-Trifluoroethan-1-ol | |
Other names
2,2,2-Trifluoroethanol | |
Identifiers | |
3D model (JSmol) |
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1733203 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.000.831 |
EC Number |
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2532 | |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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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 in ethanol | 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 | |
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 [77 °F], 100 kPa).
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Trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acyl chloride.[1]
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.[citation needed] As a co-catalyst for this conversion tertiary aliphatic amines like triethylamine are commonly employed.
Trifluoroethanol is used as a specialized solvent in organic chemistry.[2][3] Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFE.[4]
It competitively inhibits alcohol dehydrogenase for example.[5]
TFE forms complexes with Lewis bases such as THF or pyridine through hydrogen bonding, yielding 1:1 adducts.[6] 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.
TFE can be used in biochemical experiments to stabilize alpha helix.[7][8] There are also stable beta sheets in TFE, suggesting that TFE stabilizes the secondary structure the sequence has a preference for.[8]
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.[1]
Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes.[9] Research has shown it to be a testicular toxicant in rats and dogs.[10]
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