Chemistry:2,2,2-Trifluoroethanol

From HandWiki

2,2,2-Trifluoroethanol is the synthetic organic compound with the formula CF3CH2OH. Also known as TFEA 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

Trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acyl chloride.[1]

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.[2][3] Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFEA.[4]

It competitively inhibits alcohol dehydrogenase for example.[5]

TFEA 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.

TFEA can be used in biochemical experiments to stabilize alpha helix.[7][8] There are also stable beta sheets in TFEA, suggesting that TFEA 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]

Fluorester (2,2,2-trifluoroethyl methacrylate) is an ester of methacrylic acid and TFEA, which can be used as a monomer in specialty paints.[9]

Safety

Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes.[10] Research has shown it to be a testicular toxicant in rats and dogs.[11]

See also

References

  1. ↑ 1.0 1.1 "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons. 2000. doi:10.1002/14356007.a11_349. ISBN 3527306730. 
  2. ↑ "Fluorinated Alcohols: A New Medium for Selective and Clean Reaction". Synlett (1): 18–29. 2004. doi:10.1055/s-2003-44973. 
  3. ↑ "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". Synthesis 2007 (19): 2925–2943. 2007. doi:10.1055/s-2007-983902. 
  4. ↑ "Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide". Organic Syntheses 80: 184. 2003. doi:10.15227/orgsyn.080.0184. http://www.orgsyn.org/demo.aspx?prep=v80p0184. 
  5. ↑ "The competitive inhibition of yeast alcohol dehydrogenase by 2,2,2-trifluoroethanol". Biochemical Education 26 (3): 239–242. 1998. doi:10.1016/s0307-4412(98)00073-9. 
  6. ↑ "Linear enthalpy-spectral shift correlations for 2,2,2-trifluoroethanol". Journal of Physical Chemistry 74 (19): 3535–3543. 1970. doi:10.1021/j100713a017. Bibcode: 1970JPhCh..74.3535S. 
  7. ↑ "Trifluoroethanol direct interactions with protein backbones destabilize α-helices". Journal of Molecular Liquids 365. 2022-11-01. doi:10.1016/j.molliq.2022.120209. ISSN 0167-7322. https://www.sciencedirect.com/science/article/pii/S0167732222017482. 
  8. ↑ 8.0 8.1 "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. May 1992. doi:10.1073/pnas.89.10.4462. PMID 1584778. Bibcode: 1992PNAS...89.4462Z. 
  9. ↑ "New Flourine-Containing Monomer". Paint & Coatings (BNP Media). September 26, 2000. https://www.pcimag.com/articles/85085-new-flourine-containing-monomer. 
  10. ↑ "Sciencelab MSDS". http://www.sciencelab.com/msds.php?msdsId=9925323. 
  11. ↑ Fischer Scientific MSDS
  • Halocarbon Fluorochemicals
  • United States Patent number 4,647,706 "Process for the synthesis of 2,2,2-Trifluoroethanol and 1,1,1,3,3,3-Hexafluoroisopropanol"



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:2,2,2-Trifluoroethanol&oldid=4308518"