2,2,2-Trifluoroethanol

Synthesis

Trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acyl chloride.

TFEA 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 co-catalyst for this conversion tertiary aliphatic amines like triethylamine are commonly employed.

Properties

Trifluoroethanol is used as a specialized solvent in organic chemistry. Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFEA.

It competitively inhibits alcohol dehydrogenase for example.

TFEA forms complexes with Lewis bases such as THF or pyridine through hydrogen bonding, yielding 1:1 adducts. 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.

TFEA can be used in biochemical experiments to stabilize alpha helix. There are also stable beta sheets in TFEA, suggesting that TFEA stabilizes the secondary structure the sequence has a preference for.

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.

Fluorester (2,2,2-trifluoroethyl methacrylate) is an ester of methacrylic acid and TFEA, which can be used as a monomer in specialty paints.

Safety

Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes. Research has shown it to be a testicular toxicant in rats and dogs.

References

References

1. (2000). "Fluorine Compounds, Organic". [[John Wiley & Sons]].
2. (2004). "Fluorinated Alcohols: A New Medium for Selective and Clean Reaction". [[Synlett]].
3. (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". [[Synthesis (journal).
4. (2003). "Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide".
5. (1998). "The competitive inhibition of yeast alcohol dehydrogenase by 2,2,2-trifluoroethanol". Biochemical Education.
6. (1970). "Linear enthalpy-spectral shift correlations for 2,2,2-trifluoroethanol". Journal of Physical Chemistry.
7. (2022-11-01). "Trifluoroethanol direct interactions with protein backbones destabilize α-helices". Journal of Molecular Liquids.
8. (May 1992). "Environment affects amino acid preference for secondary structure". Proceedings of the National Academy of Sciences of the United States of America.
9. (September 26, 2000). "New Flourine-Containing Monomer". BNP Media.
10. "Sciencelab MSDS".
11. [http://fscimage.fishersci.com/msds/01753.htm Fischer Scientific MSDS]