2,2,2-Trifluoroethanol

Chembox new
Name = 2,2,2-Trifluoroethanol
ImageFile = 2,2,2-trifluoroethanol.svg
ImageName = 2,2,2-Trifluoroethanol
ImageFile1 = 2,2,2-trifluroroethanol-3D-vdW.png ImageName1 = 2,2,2-Trifluoroethanol
Section1 = Chembox Identifiers
SMILES = OCC(F)(F)F
CASNo = 75-89-8
Section2 = Chembox Properties
Formula = C₂H₃F₃O
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⁻¹.mol⁻¹
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 = alcohols
OtherFunctn = Hexafluoro-2-propanol
OtherCpds = 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 form stable complexes also with heterocycles (e.g. THF or pyridine) through hydrogen bonding.

ynthesis

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

TFE can also be prepare 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.Fact|date=November 2007 As a co-catalyst for this conversion tertiary aliphatic amines like triethylamine are commonly employed.

Uses

Trifluoroethanol is used as a solvent in organic chemistry. [cite journal | format = Review | author = Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. | title = Fluorinated Alcohols: A New Medium for Selective and Clean Reaction | journal = Synlett | year = 2004 | issue = 1 | pages = 18–29 | doi =10.1055/s-2003-44973] [cite journal | format = Review | author = Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin | doi = 10.1055/s-2007-983902 | title = Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis | journal = Synthesis | pages = 2925–2943 | year = 2007 | volume = 2007] Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFE. [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]

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

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.

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"