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2,2,2-Trifluoroethanol

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2,2,2-Trifluoroethanol

2,2,2-Trifluoroethanol
2,2,2-Trifluoroethanol
2,2,2-Trifluoroethanol
Identifiers
 Y
ChEBI  N
ChEMBL  N
ChemSpider  N
DrugBank  N
Jmol-3D images Image
Image
PubChem
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; 347.2 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
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).
 N  (: Y/N?)

2,2,2-Trifluoroethanol is 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 1
  • Uses 2
  • Reactions 3
  • Safety 4
  • References 5

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


  • United States Patent number 4,647,706 "Process for the synthesis of 2,2,2-Trifluoroethanol and 1,1,1,3,3,3-Hexafluoroisopropanol"
  • Halocarbon Fluorochemicals
  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".  
  3. ^ Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis".  
  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".  
  5. ^ Sciencelab MSDS
  6. ^ Fischer Scientific MSDS

References

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]

Safety

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]

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).

Reactions

Industrially trifluoroethanol is employed as a solvent for nylon as well as in applications of the pharmaceutical field.

structure of proteins. three-dimensional and proteins. Depending upon its concentration, TFE can strongly affect the peptides spectroscopy: this solvent can effectively solubilize both NMR studies with protein folding It can also be used as a protein denaturant. In biology TFE is used as a co-solvent in [4] are effectively conducted in TFE.hydrogen peroxide Oxidations of sulfur compounds using [3][2]

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