2,2,2-Trifluoroethanol

2,2,2-Trifluoroethanol

2,2,2-Trifluoroethanol

Chemical compound

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.

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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.[citation needed] As a co-catalyst 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. [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. [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. [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. [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. [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. [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. [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. [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. [9]
    "Sciencelab MSDS". Archived from the original on 2016-03-03. Retrieved 2011-11-08.
  10. [10]
    Fischer Scientific MSDS
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