2,2,2-Trifluoroethanol

2,2,2-Trifluoroethanol
Identifiers
75-89-8 YesY
ChEBI CHEBI:42330 N
ChEMBL ChEMBL116675 N
ChemSpider 21106169 N
DrugBank DB03226 N
Jmol interactive 3D Image
Image
PubChem 6409
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
? J.K−1.mol−1
? kJ/mol
-886.6 kJ/mol
Hazards
Harmful (Xn)
R-phrases R10, R20/21/22, R36/38, R62
S-phrases S16, S36/37/39, S45
NFPA 704
Flammability code 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., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
3
2
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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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.

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] It can also be used as a 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. 1 2 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". Synlett (Review) (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". Synthesis (Review) 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.
  5. ↑ Sciencelab MSDS
  6. ↑ Fischer Scientific MSDS
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