2,2,2-Trifluoroethanol

changed changed 477209561 2,2,2-Trifluoroethanol 2,2,2-trifluoroethanol.svg skin-invert-image 150px 2,2,2-Trifluoroethanol 2,2,2-trifluoroethanol-3D-vdW.png bg-transparent 150px 2,22-Trifluoroethanol 2,2,2-Trifluoroethan-1-ol 2,2,2-Trifluoroethanol 75-89-8 correct CAS 1733203 OCC(F)(F)F correct chemspider correct EBI 42330 correct EBI 116675 21106169 correct drugbank DB03226 200-913-6 2532 correct FDA 8T8I76KYF1 6409 1/C2H3F3O/c3-2(4,5)1-6/h6H,1H2 RHQDFWAXVIIEBN-UHFFFAOYAH FC(F)(F)CO changed chemspider 1S/C2H3F3O/c3-2(4,5)1-6/h6H,1H2 changed chemspider RHQDFWAXVIIEBN-UHFFFAOYSA-N C2H3F3O 100.04 g/mol Colorless liquid 1.325±0.06 g/mL @ 20 °C, 760 Torr liquid Miscible ethanol Miscible −43.5 74.0 0.9 cSt @ 37.78 °C 12.46±0.10 Most Acidic Temp: 25 °C −886.6 kJ/mol 02 05 06 07 08 Danger 226 301 312 315 318 331 332 335 360 373 201 202 210 233 240 241 242 243 260 261 264 270 271 280 281 301+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 2 1 3 alcohols Hexafluoro-2-propanol 1,1,1-Trifluoroethane Trifluoroacetic acid 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. Siegemund G, Schwertfeger W, Feiring A, Smart B, Behr F, Vogel H, McKusick B, Kirsch P Fluorine Compounds, Organic Ullmann's Encyclopedia of Industrial Chemistry John Wiley & Sons 2000 10.1002/14356007.a11_349 3527306730 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.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. Review Bégué JP, Bonnet-Delpon D, Crousse B Fluorinated Alcohols: A New Medium for Selective and Clean Reaction Synlett 2004 1 18–29 10.1055/s-2003-44973 Review Shuklov IA, Dubrovina NV, Börner A 10.1055/s-2007-983902 Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis Synthesis 2925–2943 2007 2007 19 Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFEA. Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide Ravikumar KS, Kesavan V, Crousse B, Bonnet-Delpon D, Bégué JP 80 184 2003 v80p0184 10.15227/orgsyn.080.0184 It competitively inhibits alcohol dehydrogenase for example.The competitive inhibition of yeast alcohol dehydrogenase by 2,2,2-trifluoroethanol Biochemical Education 26 3 239–242 10.1016/s0307-4412(98)00073-9 1998 Taber RL TFEA forms complexes with Lewis bases such as THF or pyridine through hydrogen bonding, yielding 1:1 adducts. Sherry AD, Purcell KF 1970 Linear enthalpy-spectral shift correlations for 2,2,2-trifluoroethanol Journal of Physical Chemistry 74 19 3535–3543 10.1021/j100713a017 1970JPhCh..74.3535S 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. Pereira AF, Piccoli V, Martínez L 2022-11-01 Trifluoroethanol direct interactions with protein backbones destabilize α-helices https://www.sciencedirect.com/science/article/pii/S0167732222017482 Journal of Molecular Liquids 365 120209 10.1016/j.molliq.2022.120209 251914912 0167-7322 subscription Zhong L, Johnson WC 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 1584778 49102 10.1073/pnas.89.10.4462 1992PNAS...89.4462Z free 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.New Flourine-Containing Monomer https://www.pcimag.com/articles/85085-new-flourine-containing-monomer 20 November 2025 Paint & Coatings BNP Media September 26, 2000 Safety Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes.http://www.sciencelab.com/msds.php?msdsId=9925323 Sciencelab MSDS 2011-11-08 https://web.archive.org/web/20160303210222/http://www.sciencelab.com/msds.php?msdsId=9925323 2016-03-03 dead Research has shown it to be a testicular toxicant in rats and dogs.http://fscimage.fishersci.com/msds/01753.htm Fischer Scientific MSDS 2011-11-08 2016-03-04 https://web.archive.org/web/20160304023436/http://fscimage.fishersci.com/msds/01753.htm dead See also Trifluoromethanol Pirkle's alcohol, 2,2,2-Trifluoro-1-(9-anthryl)ethanol References External links Halocarbon Fluorochemicals https://web.archive.org/web/20160528055305/http://www.halocarbon.com/halocarbon_media/Trifluoroethanol_208.pdf 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" Category:Halogenated solvents Category:Primary alcohols Category:GABAA receptor positive allosteric modulators Category:Glycine receptor agonists Category:Sedatives Category:Hypnotics Category:Fluoroethanols Category:Trifluoroethyl compounds Category:Trifluoromethyl compounds