2,2,2-Trifluoroethanol

2,2,2-Trifluoroethanol
Identifiers
CAS number 75-89-8 Y
PubChem 6409
ChemSpider 21106169 Y
DrugBank DB03226
ChEBI CHEBI:42330 N
ChEMBL CHEMBL116675 N
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C2H3F3O
Molar mass 100.04 g/mol
Appearance Colorless liquid
Density 1.382 g/mL, @ 25 °C liquid
Melting point

−45.0 °C
Boiling point

73.5 °C
Solubility in water Miscible
Solubility in ethanol Miscible
Viscosity 0.9 cSt @ 37.78 °C
Thermochemistry
Std enthalpy of
formation ΔfHo298		  ? kJ/mol
Std enthalpy of
combustion ΔcHo298		 -886.6 kJ/mol
Standard molar
entropy So298		  ? J.K−1.mol−1
Hazards
EU classification Harmful (Xn)
R-phrases R10, R20/21/22, R36/38, R62
S-phrases S16, S36/37/39, S45
NFPA 704
3
2
1
Related compounds
Related alcohols Hexafluoro-2-propanol
Related compounds 1,1,1-Trifluoroethane
Trifluoroacetic acid
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 forms stable complexes also with heterocycles (e.g. THF or pyridine) through hydrogen bonding.

Contents

Synthesis

Trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acid 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. 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.[2][3] Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFE.[4] Protein denaturant. 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.[1]

Safety

Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes.[5] Research has shown it to be a testicular toxicant in rats and dogs. [6]

References

  1. ^ a b 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.
  2. ^ Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. (2004). "Fluorinated Alcohols: A New Medium for Selective and Clean Reaction" (Review). Synlett (1): 18–29. doi:10.1055/s-2003-44973. 
  3. ^ Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis" (Review). Synthesis 2007 (19): 2925–2943. doi:10.1055/s-2007-983902. 
  4. ^ Kabayadi S. Ravikumar, Venkitasamy Kesavan, Benoit Crousse, Danièle Bonnet-Delpon, and Jean-Pierre Bégué (2003), "Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyle Phenyl Sulfoxide", Org. Synth. 80: 184, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=v80p0184 
  5. ^ Sciencelab MSDS
  6. ^ Fischer Scientific MSDS