2,2,2-Trifluoroethanol
From Wikipedia, the free encyclopedia
| 2,2,2-Trifluoroethanol | |
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| Identifiers | |
| CAS number | [] |
| SMILES |
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| Properties | |
| Molecular formula | C2H3F3O |
| Molar mass | 100.04 g/mol |
| Appearance | Colorless liquid |
| Density | 1.393 g/mL, liquid |
| Melting point |
−45.0 °C |
| Boiling point |
78.0 °C |
| Solubility in water | Miscible |
| Solubility in ethanol | Miscible |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
? kJ/mol |
| Std enthalpy of combustion ΔcH |
? kJ/mol |
| Standard molar entropy S |
? J.K−1.mol−1 |
| Hazards | |
| EU classification | Harmful (Xn) |
| R-phrases | R10, R20/21/22, R36/38, R62 |
| S-phrases | S16, S36/37/39, S45 |
| NFPA 704 |
 3
2
1
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| Related compounds | |
| Related alcohols | Hexafluoro-2-propanol |
| Related compounds | 1,1,1-Trifluoroethane Trifluoroacetic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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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 form stable complexes also with heterocycles (e.g. THF or pyridine) through hydrogen bonding.
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[edit] 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 prepare 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.
[edit] 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]
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.
[edit] 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]
[edit] References
- ^ 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" (Review). Synlett (1): 18–29. doi:.
- ^ Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis" (Review). Synthesis 2007: 2925–2943. doi:.
- ^ 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.
- United States Patent number 4,647,706 "Process for the synthesis of 2,2,2-Trifluoroethanol and 1,1,1,3,3,3-Hexafluoroisopropanol"
