Chemistry:2,2,2-Trifluoroethanol

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2,2,2-Trifluoroethanol
2,2,2-Trifluoroethanol
2,22-Trifluoroethanol
Names
Preferred IUPAC name
2,2,2-Trifluoroethan-1-ol
Other names
2,2,2-Trifluoroethanol
Identifiers
3D model (JSmol)
1733203
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 200-913-6
2532
UNII
Properties
C2H3F3O
Molar mass 100.04 g/mol
Appearance Colorless liquid
Density 1.325±0.06 g/mL @ 20 °C, 760 Torr liquid
Melting point −43.5 °C (−46.3 °F; 229.7 K)
Boiling point 74.0 °C (165.2 °F; 347.1 K)
Miscible
Solubility in ethanol Miscible
Acidity (pKa) 12.46±0.10 Most Acidic Temp: 25 °C
Viscosity 0.9 cSt @ 37.78 °C
Thermochemistry
-886.6 kJ/mol
Hazards
GHS pictograms GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: HarmfulGHS08: Health hazard
GHS Signal word Danger
H226, H301, H312, H315, H318, H331, H332, H335, H360, H373
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+310, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P308+313, P310, P311, P312
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
2
1
Related compounds
Related alcohols
 Hexafluoro-2-propanol
Related compounds
 1,1,1-Trifluoroethane
Trifluoroacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

2,2,2-Trifluoroethanol is the organic compound with the formula CF3CH2OH. 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 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]

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] 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 TFE.[4]

It competitively inhibits alcohol dehydrogenase for example.[5]

TFE 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.

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

Safety

Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes.[9] Research has shown it to be a testicular toxicant in rats and dogs.[10]

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. 
  7. ↑ "Trifluoroethanol direct interactions with protein backbones destabilize α-helices". Journal of Molecular Liquids 365: 120209. 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. ↑ "Sciencelab MSDS". http://www.sciencelab.com/msds.php?msdsId=9925323. 
  10. ↑ Fischer Scientific MSDS

External links

  • 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"



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