View source for 2,2,2-Trifluoroethanol

{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 477209561
|Name = 2,2,2-Trifluoroethanol
|ImageFile = 2,2,2-trifluoroethanol.svg
|ImageSize = 150px
|ImageName = 2,2,2-Trifluoroethanol
|ImageFile1 = 2,2,2-trifluoroethanol-3D-vdW.png
|ImageSize1 = 150px
|ImageName1 = 2,22-Trifluoroethanol
|PIN = 2,2,2-Trifluoroethan-1-ol
|OtherNames = 2,2,2-Trifluoroethanol
|Section1={{Chembox Identifiers
|CASNo = 75-89-8
|CASNo_Ref = {{cascite|correct|CAS}}
|Beilstein = 1733203
|SMILES = OCC(F)(F)F
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 42330
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 116675
|ChemSpiderID = 21106169
|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
|DrugBank = DB03226
|EC_number = 200-913-6
|Gmelin = 2532
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 8T8I76KYF1
|PubChem = 6409
|InChI = 1/C2H3F3O/c3-2(4,5)1-6/h6H,1H2
|InChIKey = RHQDFWAXVIIEBN-UHFFFAOYAH
|SMILES1 = FC(F)(F)CO
|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
|StdInChI = 1S/C2H3F3O/c3-2(4,5)1-6/h6H,1H2
|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
|StdInChIKey = RHQDFWAXVIIEBN-UHFFFAOYSA-N 
}}
|Section2={{Chembox Properties
|Formula = C<sub>2</sub>H<sub>3</sub>F<sub>3</sub>O
|MolarMass = 100.04 g/mol
|Appearance = Colorless liquid
|Density = 1.325±0.06 g/mL @ 20 °C, 760 Torr liquid
|Solubility = Miscible
|Solvent = [[ethanol]]
|SolubleOther = Miscible
|MeltingPtC = −43.5
|BoilingPtC = 74.0
|Viscosity = 0.9 cSt @ 37.78 °C
|pKa = 12.46±0.10 Most Acidic Temp: 25 °C
}}
|Section3={{Chembox Thermochemistry
|DeltaHc = −886.6 kJ/mol
}}
|Section4={{Chembox Hazards
|GHSPictograms = {{GHS02}}{{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|226|301|312|315|318|331|332|335|360|373}}
|PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|260|261|264|270|271|280|281|301+310|302+352|303+361+353|304+312|304+340|305+351+338|308+313|310|311|312|314|321|322|330|332+313|362|363|370+378|403+233|403+235|405|501}}
|NFPA-H = 2
|NFPA-R = 1
|NFPA-F = 3
}}
|Section5={{Chembox Related
|OtherFunction_label = [[Alcohol (chemistry)|alcohol]]s
|OtherFunction = [[Hexafluoro-2-propanol]]
|OtherCompounds = [[1,1,1-Trifluoroethane]]<br /> [[Trifluoroacetic acid]]
}}
}}

'''2,2,2-Trifluoroethanol''' is the [[organic compound]] with the [[chemical formula|formula]] CF<sub>3</sub>CH<sub>2</sub>OH. 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 (chemistry)|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.<ref name=Gunt>{{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}}</ref>

TFE can also be prepared by [[hydrogenolysis]] of compounds of generic formula CF<sub>3</sub>−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.

==Properties==
Trifluoroethanol is used as a specialized [[solvent]] in organic chemistry.<ref>{{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}}</ref><ref>{{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 (journal)|Synthesis]] | pages = 2925–2943 | year = 2007 | volume = 2007 | issue = 19}}</ref> Oxidations of sulfur compounds using [[hydrogen peroxide]] are effectively conducted in TFE.<ref>{{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}}</ref>

It competitively inhibits alcohol dehydrogenase for example.<ref>{{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 }}</ref>

TFE forms complexes with Lewis bases such as [[THF]] or [[pyridine]] through [[hydrogen bond]]ing, yielding 1:1 adducts.<ref>{{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}}</ref> It is classified as a [[HSAB theory|hard Lewis acid]] and its acceptor properties are discussed in the [[ECW model]] yielding E<sub>A</sub> = 2.07 and C<sub>A</sub> = 1.06.

TFE can be used in [[Biochemistry|biochemical]] experiments to stabilize [[alpha helix]].<ref>{{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 }}</ref><ref name=":0">{{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 }}</ref> There are also stable [[Beta sheet|beta sheets]] in TFE, suggesting that TFE stabilizes the secondary structure the sequence has a preference for.<ref name=":0" />

==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]]).

[[Fluroxene|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]].<ref name=Gunt/>

==Safety==
Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes.<ref>{{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 }}</ref> Research has shown it to be a testicular toxicant in rats and dogs.<ref>[http://fscimage.fishersci.com/msds/01753.htm Fischer Scientific MSDS]</ref>

== See also ==
*[[Trifluoromethanol]]

== References == 
<references />

== External links ==
* [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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{{DEFAULTSORT:Trifluoroethanol, 2, 2, 2-}}
[[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]]