2,2,2-Trifluoroethanol
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2008-06-28T09:11:48Z
Alexbot
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robot Modifying: [[zh:三氟乙醇]]
{{Chembox new
| Name = 2,2,2-Trifluoroethanol
| ImageFile = 2,2,2-trifluoroethanol.svg
<!-- | ImageSize = 150px -->
| ImageName = 2,2,2-Trifluoroethanol
| ImageFile1 = 2,2,2-trifluroroethanol-3D-vdW.png
<!-- | ImageSize1 = 150px -->
| ImageName1 = 2,2,2-Trifluoroethanol
| Section1 = {{Chembox Identifiers
| SMILES = OCC(F)(F)F
| CASNo = 75-89-8
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>2</sub>H<sub>3</sub>F<sub>3</sub>O
| MolarMass = 100.04 g/mol
| Appearance = Colorless liquid
| Density = 1.393 g/mL, liquid
| Solubility = Miscible
| Solvent = [[ethanol]]
| SolubleOther = Miscible
| MeltingPt = −45.0 °C
| BoilingPt = 78.0 °C
| Viscosity =
}}
| Section4 = {{Chembox Thermochemistry
| DeltaHf = ? kJ/mol
| DeltaHc = ? kJ/mol
| Entropy = ? J.K<sup>−1</sup>.mol<sup>−1</sup>
}}
| Section7 = {{Chembox Hazards
| EUClass = Harmful ('''Xn''')
| RPhrases = R10, R20/21/22, R36/38, R62
| SPhrases = S16, S36/37/39, S45
| NFPA-H = 2
| NFPA-R = 1
| NFPA-F = 3
}}
| Section8 = {{Chembox Related
| Function = [[alcohol]]s
| OtherFunctn = [[Hexafluoro-2-propanol]]
| OtherCpds = [[1,1,1-Trifluoroethane]]<br /> [[Trifluoroacetic acid]]
}}
}}
'''2,2,2-Trifluoroethanol''' is the [[organic compound]] with the [[chemical formula|formula]] CF<sub>3</sub>CH<sub>2</sub>OH. 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 [[Heterocyclic compound|heterocycles]] (e.g. [[THF]] or [[pyridine]]) through [[hydrogen bond]]ing.
===Synthesis===
Trifluoroethanol is produced industrially by [[hydrogenation]] or the hydride reduction of derivatives of [[trifluoroacetic acid]], such as the esters or acid chloride.<ref name=Gunt>Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, 2007.</ref>
TFE can also be prepare by [[hydrogenolysis]] of compounds of generic formula CF<sub>3</sub>−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]].{{Fact|date=November 2007}} As a co-catalyst for this conversion tertiary aliphatic amines like [[triethylamine]] are commonly employed.
===As a solvent===
Trifluoroethanol is used as a [[solvent]] in organic chemistry <ref> ''Review'': Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Fluorinated Alcohols: A New Medium for Selective and Clean Reaction. ''Synthesis'', '''2004''',(1), pp. 18-29.</ref>, <ref>''Review'': Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin {{doi-inline|10.1055/s-2007-983902|Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis}}, ''Synthesis'', '''2007''', pp. 2925-2943</ref>. Oxidations of sulfur compounds using [[hydrogen peroxide]] are effectively conducted in TFE.<ref>{{OrgSynth | title = Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyle Phenyl Sulfoxide| author = Kabayadi S. Ravikumar, Venkitasamy Kesavan, Benoit Crousse, Danièle Bonnet-Delpon, and Jean-Pierre Bégué | volume = 80 | pages = 184 | year = 2003 | prep = v80p0184}}</ref>
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 [[dimension|three-dimensional]] structure of proteins.
Industrially trifluoroethanol is employed as a solvent for [[nylon]] as well as in applications of the pharmaceutical field.
===Reactions===
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-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]].<ref name=Gunt/>
==References==
<references/>
* [http://www.halocarbon.com/fluorochemicals/trifluoroethanol.shtml Halocarbon Fluorochemicals]
* United States Patent number 4,647,706 "Process for the synthesis of 2,2,2-Trifluoroethanol and 1,1,1,3,3,3-Hexafluoroisopropanol"
{{DEFAULTSORT:Trifluoroethanol,2,2,2-}}
[[Category:Organofluorides]]
[[Category:Halogenated solvents]]
[[Category:Alcohols]]
[[ru:Трифторэтанол]]
[[zh:三氟乙醇]]