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
CAS Number
3D model (JSmol)
Beilstein Reference
 1733203
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.831
EC Number
  • 200-913-6
Gmelin Reference
 2532
PubChem CID
UNII
InChI
  • InChI=1S/C2H3F3O/c3-2(4,5)1-6/h6H,1H2 N
    Key: RHQDFWAXVIIEBN-UHFFFAOYSA-N N
  • InChI=1/C2H3F3O/c3-2(4,5)1-6/h6H,1H2
    Key: RHQDFWAXVIIEBN-UHFFFAOYAH
SMILES
  • OCC(F)(F)F
  • FC(F)(F)CO
Properties
Chemical formula
 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)
Solubility in water
 Miscible
Solubility in ethanol Miscible
Acidity (pKa) 12.46±0.10 Most Acidic Temp: 25 °C
Viscosity 0.9 cSt @ 37.78 °C
Thermochemistry
Std molar
entropy (S⦵298)
  ? J.K−1.mol−1
Std enthalpy of
formation (ΔfH⦵298)
  ? kJ/mol
Std enthalpy of
combustion (ΔcH⦵298)
 -886.6 kJ/mol
Hazards
GHS labelling:
Pictograms
Signal word
 Danger
Hazard statements
 H226, H301, H312, H315, H318, H331, H332, H335, H360, H373
Precautionary statements
 P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P314, P321, P322, P330, P332+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
2
3
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
  • Trifluoromethanol

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 Archived 2016-05-28 at the Wayback Machine
  • United States Patent number 4,647,706 "Process for the synthesis of 2,2,2-Trifluoroethanol and 1,1,1,3,3,3-Hexafluoroisopropanol"
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.