2,2,2-Trifluoroethanol
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Names | |
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Preferred IUPAC name
2,2,2-Trifluoroethan-1-ol
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Other names
2,2,2-Trifluoroethanol
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Identifiers | |
75-89-8 ![]() |
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3D model (Jmol) | Interactive image Interactive image |
ChEBI | CHEBI:42330 ![]() |
ChEMBL | ChEMBL116675 ![]() |
ChemSpider | 21106169 ![]() |
DrugBank | DB03226 ![]() |
ECHA InfoCard | 100.000.831 |
PubChem | 6409 |
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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 | |
Std molar
entropy (S |
? J.K−1.mol−1 |
Std enthalpy of
formation (ΔfH |
? kJ/mol |
Std enthalpy of
combustion (ΔcH |
-886.6 kJ/mol |
Hazards | |
EU classification (DSD)
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Harmful (Xn) |
R-phrases | R10, R20/21/22, R36/38, R62 |
S-phrases | S16, S36/37/39, S45 |
NFPA 704 | |
Related compounds | |
Related alcohols
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Hexafluoro-2-propanol |
Related compounds
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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.
Contents
Synthesis[edit]
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.[citation needed] As a co-catalyst for this conversion tertiary aliphatic amines like triethylamine are commonly employed.
Uses[edit]
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[citation needed]. 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[edit]
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 Fluoromar, features a vinylether of trifluorethanol. This species was prepared by the reaction of trifluoroethanol with acetylene.[1]
Safety[edit]
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[edit]
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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 Methyle Phenyl Sulfoxide". Org. Synth. 80: 184.
- ^ Sciencelab MSDS
- ^ 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"