2,2,2-Trifluoroethanol

Chemical compound From Wikipedia, the free encyclopedia

2,2,2-Trifluoroethanol is the synthetic organic compound with the formula CF3CH2OH. Also known as TFEA 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.

Quick facts Names, Identifiers ...
2,2,2-Trifluoroethanol
2,2,2-Trifluoroethanol
2,2,2-Trifluoroethanol
2,22-Trifluoroethanol
2,22-Trifluoroethanol
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 Edit this at Wikidata
EC Number
  • 200-913-6
2532
UNII
  • InChI=1S/C2H3F3O/c3-2(4,5)1-6/h6H,1H2 ☒N
    Key: RHQDFWAXVIIEBN-UHFFFAOYSA-N ☒N
  • InChI=1/C2H3F3O/c3-2(4,5)1-6/h6H,1H2
    Key: RHQDFWAXVIIEBN-UHFFFAOYAH
  • OCC(F)(F)F
  • FC(F)(F)CO
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
−886.6 kJ/mol
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H226, H301, H312, H315, H318, H331, H332, H335, H360, H373
P201, P202, P210, P233, P240, P241, P242, P243, P260, 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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
3
1
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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Synthesis

Trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acyl chloride.[1]

TFEA 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.

Properties

Trifluoroethanol is used as a specialized solvent in organic chemistry.[2][3] Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFEA.[4]

It competitively inhibits alcohol dehydrogenase for example.[5]

TFEA 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.

TFEA can be used in biochemical experiments to stabilize alpha helix.[7][8] There are also stable beta sheets in TFEA, suggesting that TFEA stabilizes the secondary structure the sequence has a preference for.[8]

Reactions

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]

Fluorester (2,2,2-trifluoroethyl methacrylate) is an ester of methacrylic acid and TFEA, which can be used as a monomer in specialty paints.[9]

Safety

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]

See also

References

External links

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