2,2,2-Trifluoroethanol

Trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acyl chloride.{{cite encyclopedia| vauthors = Siegemund G, Schwertfeger W, Feiring A, Smart B, Behr F, Vogel H, McKusick B, Kirsch P |title = Fluorine Compounds, Organic|encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry|publisher = John Wiley & Sons|year = 2000|doi = 10.1002/14356007.a11_349|isbn = 3527306730}}

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|date=November 2007}} As a co-catalyst for this conversion tertiary aliphatic amines like triethylamine are commonly employed.

Trifluoroethanol is used as a specialized solvent in organic chemistry.{{cite journal | type = Review | vauthors = Bégué JP, Bonnet-Delpon D, Crousse B | title = Fluorinated Alcohols: A New Medium for Selective and Clean Reaction | journal = Synlett | year = 2004 | issue = 1 | pages = 18–29 | doi =10.1055/s-2003-44973}}{{cite journal | type = Review | vauthors = Shuklov IA, Dubrovina NV, Börner A | doi = 10.1055/s-2007-983902 | title = Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis | journal = Synthesis | pages = 2925–2943 | year = 2007 | volume = 2007 | issue = 19}} Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFE.{{OrgSynth | title = Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide| vauthors = Ravikumar KS, Kesavan V, Crousse B, Bonnet-Delpon D, Bégué JP | volume = 80 | pages = 184 | year = 2003 | prep = v80p0184 | doi = 10.15227/orgsyn.080.0184}}

It competitively inhibits alcohol dehydrogenase for example.{{Cite journal|title=The competitive inhibition of yeast alcohol dehydrogenase by 2,2,2-trifluoroethanol|journal=Biochemical Education|volume=26|issue=3|pages=239–242|doi=10.1016/s0307-4412(98)00073-9|year=1998| vauthors = Taber RL }}

TFE forms complexes with Lewis bases such as THF or pyridine through hydrogen bonding, yielding 1:1 adducts.{{cite journal| vauthors = Sherry AD, Purcell KF |year=1970|title=Linear enthalpy-spectral shift correlations for 2,2,2-trifluoroethanol|journal=Journal of Physical Chemistry|volume=74|issue= 19 |pages=3535–3543|doi=10.1021/j100713a017}} It is classified as a hard Lewis acid and its acceptor properties are discussed in the ECW model yielding E_A = 2.07 and C_A = 1.06.

TFE can be used in biochemical experiments to stabilize alpha helix.{{Cite journal | vauthors = Pereira AF, Piccoli V, Martínez L |date=2022-11-01 |title=Trifluoroethanol direct interactions with protein backbones destabilize α-helices |url=https://www.sciencedirect.com/science/article/pii/S0167732222017482 |journal=Journal of Molecular Liquids |volume=365 |pages=120209 |doi=10.1016/j.molliq.2022.120209 |s2cid=251914912 |issn=0167-7322|url-access=subscription }}{{cite journal | vauthors = Zhong L, Johnson WC | title = Environment affects amino acid preference for secondary structure | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 89 | issue = 10 | pages = 4462–4465 | date = May 1992 | pmid = 1584778 | pmc = 49102 | doi = 10.1073/pnas.89.10.4462 | bibcode = 1992PNAS...89.4462Z | doi-access = free }} There are also stable beta sheets in TFE, suggesting that TFE stabilizes the secondary structure the sequence has a preference for.

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.

Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes.{{Cite web |url=http://www.sciencelab.com/msds.php?msdsId=9925323 |title=Sciencelab MSDS |access-date=2011-11-08 |archive-url=https://web.archive.org/web/20160303210222/http://www.sciencelab.com/msds.php?msdsId=9925323 |archive-date=2016-03-03 |url-status=dead }} Research has shown it to be a testicular toxicant in rats and dogs.[http://fscimage.fishersci.com/msds/01753.htm Fischer Scientific MSDS]

• Trifluoromethanol

== References ==

• [http://www.halocarbon.com/halocarbon_media/Trifluoroethanol_208.pdf Halocarbon Fluorochemicals] {{Webarchive|url=https://web.archive.org/web/20160528055305/http://www.halocarbon.com/halocarbon_media/Trifluoroethanol_208.pdf |date=2016-05-28 }}
• United States Patent number 4,647,706 "Process for the synthesis of 2,2,2-Trifluoroethanol and 1,1,1,3,3,3-Hexafluoroisopropanol"

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Category:Halogenated solvents

Category:Primary alcohols

Category:GABAA receptor positive allosteric modulators

Category:Glycine receptor agonists

Category:Sedatives

Category:Hypnotics

Category:Fluoroethanols

Category:Trifluoromethyl compounds