en 2,2,2-Trifluoroethanol

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
CAS Number	75-89-8 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1733203
ChEBI	CHEBI:42330 ;
ChEMBL	ChEMBL116675 ;
ChemSpider	21106169 ;
DrugBank	DB03226 ;
ECHA InfoCard	100.000.831
EC Number	200-913-6;
Gmelin Reference	2532
PubChem CID	6409;
UNII	8T8I76KYF1 ;
CompTox Dashboard (EPA)	DTXSID0021751 ;
	InChI InChI=1S/C2H3F3O/c3-2(4,5)1-6/h6H,1H2 Key: RHQDFWAXVIIEBN-UHFFFAOYSA-N ; InChI=1/C2H3F3O/c3-2(4,5)1-6/h6H,1H2 Key: RHQDFWAXVIIEBN-UHFFFAOYAH;
	SMILES OCC(F)(F)F; FC(F)(F)CO;
Properties
Chemical formula	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)
Solubility in water	Miscible
Solubility in ethanol	Miscible
Acidity (pKa)	12.46±0.10 Most Acidic Temp: 25 °C
Viscosity	0.9 cSt @ 37.78 °C
Thermochemistry
Std enthalpy of; combustion (ΔcH⦵298)	-886.6 kJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H312, H315, H318, H331, H332, H335, H360, H373
Precautionary statements	P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P314, P321, P322, P330, P332+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)	2 3 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). verify (what is ?) Infobox references

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 E_A = 2.07 and C_A = 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]

References

^ ^a ^b Siegemund G, Schwertfeger W, Feiring A, Smart B, Behr F, Vogel H, McKusick B, Kirsch P (2000). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons. doi:10.1002/14356007.a11_349. ISBN 3527306730.
^ Bégué JP, Bonnet-Delpon D, Crousse B (2004). "Fluorinated Alcohols: A New Medium for Selective and Clean Reaction". Synlett (Review) (1): 18–29. doi:10.1055/s-2003-44973.
^ Shuklov IA, Dubrovina NV, Börner A (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". Synthesis (Review). 2007 (19): 2925–2943. doi:10.1055/s-2007-983902.
^ Ravikumar KS, Kesavan V, Crousse B, Bonnet-Delpon D, Bégué JP (2003). "Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide". Organic Syntheses. 80: 184. doi:10.15227/orgsyn.080.0184.
^ Taber RL (1998). "The competitive inhibition of yeast alcohol dehydrogenase by 2,2,2-trifluoroethanol". Biochemical Education. 26 (3): 239–242. doi:10.1016/s0307-4412(98)00073-9.
^ Sherry AD, Purcell KF (1970). "Linear enthalpy-spectral shift correlations for 2,2,2-trifluoroethanol". Journal of Physical Chemistry. 74 (19): 3535–3543. doi:10.1021/j100713a017.
^ Pereira AF, Piccoli V, Martínez L (2022-11-01). "Trifluoroethanol direct interactions with protein backbones destabilize α-helices". Journal of Molecular Liquids. 365: 120209. doi:10.1016/j.molliq.2022.120209. ISSN 0167-7322. S2CID 251914912.
^ ^a ^b Zhong L, Johnson WC (May 1992). "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. Bibcode:1992PNAS...89.4462Z. doi:10.1073/pnas.89.10.4462. PMC 49102. PMID 1584778.
^ "Sciencelab MSDS". Archived from the original on 2016-03-03. Retrieved 2011-11-08.
^ Fischer Scientific MSDS

External links

Halocarbon Fluorochemicals Archived 2016-05-28 at the Wayback Machine
United States Patent number 4,647,706 "Process for the synthesis of 2,2,2-Trifluoroethanol and 1,1,1,3,3,3-Hexafluoroisopropanol"

[Gunt-1] Siegemund G, Schwertfeger W, Feiring A, Smart B, Behr F, Vogel H, McKusick B, Kirsch P (2000). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons. doi:10.1002/14356007.a11_349. ISBN 3527306730.

[2] Bégué JP, Bonnet-Delpon D, Crousse B (2004). "Fluorinated Alcohols: A New Medium for Selective and Clean Reaction". Synlett (Review) (1): 18–29. doi:10.1055/s-2003-44973.

[3] Shuklov IA, Dubrovina NV, Börner A (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". Synthesis (Review). 2007 (19): 2925–2943. doi:10.1055/s-2007-983902.

[4] Ravikumar KS, Kesavan V, Crousse B, Bonnet-Delpon D, Bégué JP (2003). "Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide". Organic Syntheses. 80: 184. doi:10.15227/orgsyn.080.0184.

[5] Taber RL (1998). "The competitive inhibition of yeast alcohol dehydrogenase by 2,2,2-trifluoroethanol". Biochemical Education. 26 (3): 239–242. doi:10.1016/s0307-4412(98)00073-9.

[6] Sherry AD, Purcell KF (1970). "Linear enthalpy-spectral shift correlations for 2,2,2-trifluoroethanol". Journal of Physical Chemistry. 74 (19): 3535–3543. doi:10.1021/j100713a017.

[7] Pereira AF, Piccoli V, Martínez L (2022-11-01). "Trifluoroethanol direct interactions with protein backbones destabilize α-helices". Journal of Molecular Liquids. 365: 120209. doi:10.1016/j.molliq.2022.120209. ISSN 0167-7322. S2CID 251914912.

[:0-8] Zhong L, Johnson WC (May 1992). "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. Bibcode:1992PNAS...89.4462Z. doi:10.1073/pnas.89.10.4462. PMC 49102. PMID 1584778.

[9] "Sciencelab MSDS". Archived from the original on 2016-03-03. Retrieved 2011-11-08.

[10] Fischer Scientific MSDS

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2,2,2-Trifluoroethanol