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
2,2,2-Trifluoroethanol
2,22-Trifluoroethanol
Names
Preferred IUPAC name
2,2,2-Trifluoroethan-1-ol
Other names
2,2,2-Trifluoroethanol
Identifiers
3D model (JSmol)
1733203
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.831
EC Number
  • 200-913-6
2532
UNII
  • 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
  • OCC(F)(F)F
  • FC(F)(F)CO
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
-886.6 kJ/mol
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
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)
NFPA 704 four-colored 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).
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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 cocatalyst for this conversion tertiary aliphatic amines like triethylamine are commonly employed.

Properties

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

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

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

References
  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.
  8. 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.
  9. "Sciencelab MSDS". Archived from the original on 2016-03-03. Retrieved 2011-11-08.
  10. Fischer Scientific MSDS
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