2,2,2-Trifluoroethanol

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.

2,2,2-Trifluoroethanol
Names
Preferred IUPAC name
2,2,2-Trifluoroethan-1-ol
Other names
2,2,2-Trifluoroethanol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.831
UNII
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R-phrases (outdated) R10, R20/21/22, R36/38, R62
S-phrases (outdated) S16, S36/37/39, S45
NFPA 704 (fire diamond)
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. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
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 verify (what is YN ?)
Infobox references

Synthesis

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

Trifluoroethanol is a key precursor for the inhaled anaesthetic isoflurane, listed on the World Health Organization's List of Essential Medicines.

Trifluoroethanol is also used in biochemistry as an inhibitor to study enzymes. It competitively inhibits alcohol dehydrogenase for example.[5]

Reactions

Oxidation of trifluoroethanol yields trifluoroacetaldehyde or trifluoroacetic acid. It also serves as a source of the trifluoroethoxy group for various chemical reactions (Still-Gennari modification of HWE reaction).

2,2,2-Trifluoroethyl vinyl ether, an inhaled drug introduced clinically under the tradename Fluoromar, features a vinyl ether of trifluorethanol. This species was prepared by the reaction of trifluoroethanol with acetylene.[1]

TFE forms stable complexes with Lewis bases such as THF or pyridine through hydrogen bonding, yielding 1:1 adducts. [6] CF3CH2OH is classified as a hard Lewis acid and its acceptor properties are discussed in the ECW model yielding EA = 2.07 and CA = 1.06.

Safety

Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes.[7] Research has shown it to be a testicular toxicant in rats and dogs.[8]

See also

References
  1. Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2000). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons. doi:10.1002/14356007.a11_349. ISBN 3527306730.
  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 & Jean-Pierre Bégué (2003). "Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide". Organic Syntheses. 80: 184. doi:10.15227/orgsyn.080.0184.
  5. Taber, Richard L. (1998). "The competitive inhibition of yeast alcohol dehydrogenase by 2,2,2-trifluoroethanol". Biochemical Education. 26 (3): 239–242. doi:10.1016/s0307-4412(98)00073-9.
  6. Sherry,A. D.; Purcell, K. F. (1970). "Linear enthalpy-spectral shift correlations for 2,2,2-trifluoroethanol". Journal of Physical Chemistry. 74 (19): 3535–3543. doi:10.1021/j100713a017.
  7. "Sciencelab MSDS". Archived from the original on 2016-03-03. Retrieved 2011-11-08.
  8. Fischer Scientific MSDS
  • 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"
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