2,2,2-Trifluoroethanol
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| Names | |
|---|---|
| Preferred IUPAC name
2,2,2-Trifluoroethan-1-ol | |
| Other names
2,2,2-Trifluoroethanol
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| Identifiers | |
3D model (JSmol)
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| 1733203 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.000.831 |
| EC Number |
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| 2532 | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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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 enthalpy of
combustion (ΔcH⦵298) |
-886.6 kJ/mol |
| Hazards | |
| GHS labelling: | |
    
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| Danger | |
| H226, H301, H312, H315, H318, H331, H332, H335, H360, H373 | |
| 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) | |
| 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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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.
Synthesis
[edit]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.[citation needed] As a co-catalyst for this conversion tertiary aliphatic amines like triethylamine are commonly employed.
Properties
[edit]Trifluoroethanol is used as a specialized solvent in organic chemistry.[2][3] Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFE.[4]
It competitively inhibits alcohol dehydrogenase for example.[5]
TFE forms complexes with Lewis bases such as THF or pyridine through hydrogen bonding, yielding 1:1 adducts.[6] It 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.
TFE can be used in biochemical experiments to stabilize alpha helix.[7][8] There are also stable beta sheets in TFE, suggesting that TFE stabilizes the secondary structure the sequence has a preference for.[8]
Reactions
[edit]Oxidation of trifluoroethanol yields 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]
Safety
[edit]Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes.[9] Research has shown it to be a testicular toxicant in rats and dogs.[10]
See also
[edit]References
[edit]- ^ a b Siegemund G, Schwertfeger W, Feiring A, Smart B, Behr F, Vogel H, McKusick B, Kirsch P (2000). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons. doi:10.1002/14356007.a11_349. ISBN 3527306730.
- ^ Bégué JP, 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 IA, Dubrovina NV, Börner A (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". Synthesis (Review). 2007 (19): 2925–2943. doi:10.1055/s-2007-983902.
- ^ Ravikumar KS, Kesavan V, Crousse B, Bonnet-Delpon D, Bégué JP (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.
- ^ Taber RL (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.
- ^ Sherry AD, Purcell KF (1970). "Linear enthalpy-spectral shift correlations for 2,2,2-trifluoroethanol". Journal of Physical Chemistry. 74 (19): 3535–3543. doi:10.1021/j100713a017.
- ^ Pereira AF, Piccoli V, Martínez L (2022-11-01). "Trifluoroethanol direct interactions with protein backbones destabilize α-helices". Journal of Molecular Liquids. 365: 120209. doi:10.1016/j.molliq.2022.120209. ISSN 0167-7322. S2CID 251914912.
- ^ a b Zhong L, Johnson WC (May 1992). "Environment affects amino acid preference for secondary structure". Proceedings of the National Academy of Sciences of the United States of America. 89 (10): 4462–4465. Bibcode:1992PNAS...89.4462Z. doi:10.1073/pnas.89.10.4462. PMC 49102. PMID 1584778.
- ^ "Sciencelab MSDS". Archived from the original on 2016-03-03. Retrieved 2011-11-08.
- ^ Fischer Scientific MSDS
External links
[edit]- 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"