関: trifluoroethanol

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/06/21 18:12:48」(JST)

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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. Thus, TFE forms stable complexes also with heterocycles (e.g. THF or pyridine) through hydrogen bonding.

Synthesis

Trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acid 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.

Uses

Trifluoroethanol is used as a solvent in organic chemistry.^[2]^[3] Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFE.^[4] It can also be used as a protein denaturant. In biology TFE is used as a co-solvent in protein folding studies with NMR spectroscopy: this solvent can effectively solubilize both peptides and proteins^{[citation needed]}. Depending upon its concentration, TFE can strongly affect the three-dimensional structure of proteins.

Industrially trifluoroethanol is employed as a solvent for nylon as well as in applications of the pharmaceutical field.

Reactions

Oxidation of trifluoroethanol yields trifluoroacetaldehyde or trifluoroacetic acid. It also serves as a source of the trifluoromethyl group for various chemical reactions (Still-Gennari modification of HWE reaction).

2,2,2-trifluoro-1-vinyloxyethane, an inhaled drug introduced clinically under the tradename Fluromar, features a vinylether 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.^[5] Research has shown it to be a testicular toxicant in rats and dogs. ^[6]

References

^ ^a ^b Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, 2007.
^ Bégué, J.-P.; 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, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". Synthesis (Review) 2007 (19): 2925–2943. doi:10.1055/s-2007-983902.
^ Kabayadi S. Ravikumar, Venkitasamy Kesavan, Benoit Crousse, Danièle Bonnet-Delpon, and Jean-Pierre Bégué (2003), "Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyle Phenyl Sulfoxide", Org. Synth. 80: 184
^ Sciencelab MSDS
^ Fischer Scientific MSDS

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"

English Journal

Cosolvent, ions, and temperature effects on the structural properties of cecropin A-Magainin 2 hybrid peptide in solutions.

Sarukhanyan E1, Milano G, Roccatano D.
Biopolymers.Biopolymers.2015 Jan;103(1):1-14. doi: 10.1002/bip.22529.
Antimicrobial peptides are promising alternative to traditional antibiotics and antitumor drugs for the battle against new antibiotic resistant bacteria strains and cancer maladies. The study of their structural and dynamics properties at physiological conditions can help to understand their stabili
PMID 25059842

Retro operation on the Trp-cage miniprotein sequence produces an unstructured molecule capable of folding similar to the original only upon 2,2,2-trifluoroethanol addition.

Vymětal J1, Bathula SR2, Cerný J3, Chaloupková R4, Zídek L2, Sklenář V2, Vondrášek J5.
Protein engineering, design & selection : PEDS.Protein Eng Des Sel.2014 Dec;27(12):463-72. doi: 10.1093/protein/gzu046. Epub 2014 Oct 24.
Amino acid sequence and environment are the most important factors determining the structure, stability and dynamics of proteins. To evaluate their roles in the process of folding, we studied a retroversion of the well-described Trp-cage miniprotein in water and 2,2,2-trifluoroethanol (TFE) solution
PMID 25344682

Conformational behaviour and aggregation of chickpea cystatin in trifluoroethanol: Effects of epicatechin and tannic acid.

Bhat SA1, Bano B2.
Archives of biochemistry and biophysics.Arch Biochem Biophys.2014 Nov 15;562:51-61. doi: 10.1016/j.abb.2014.08.015. Epub 2014 Aug 28.
Conformational alterations and aggregates of chickpea cystatin (CPC) were investigated upon sequential addition of trifluoroethanol (TFE) over a range of 0-70% v/v. CPC on 30% and 40% v/v TFE addition exhibited non-native β-sheet, altered intrinsic fluorescence, increased thioflavin T fluorescence,
PMID 25173679

Japanese Journal

酸化カルシウムの溶解によるエチレングリコールの物性変化とその抑制

上原伸夫,田中彰
ふぇらむ = Bulletin of the Iron and Steel Institute of Japan : (一社)日本鉄鋼協会会報 100(7), 911-918, 2014
… Especially, addition of 2,2,2 -trifluoroethanol reduced the variation of analytical values of free calcium oxide contents in the steel slag even though slight decrease in the analytical values. …
NAID 130004540852

Isomer-Selected Vibrational Spectra of Solvated 2-Fluoropyridine Clusters with Water and 2,2,2-Trifluoroethanol Mixture : Effect of Cluster Formation on Conformation and Solvation Structure

Yamada Yuji,Noboru Yusuke,Sakaguchi Takuma [他],Nibu Yoshinori
福岡大学理学集報 42(2), 109-124, 2012-09
NAID 110009477393

Comparison of the Efficacy of Alpha-Lactalbumin from Equine, Bovine, and Human Milk in the Growth of Intestinal IEC-6 Cells

XIJIER,MORI Yuki,FUKUOKA Mayuko [他],CAIRANG ZHUOMA,INAGAKI Mizuho,IWAMOTO Satoshi,YABE Tomio,KANAMARU Yoshihiro
Bioscience, biotechnology, and biochemistry 76(4), 843-846, 2012-04-23
… However, after treatment with trifluoroethanol (TFE), all three α-LAs exhibited cytotoxicity. …
NAID 10030752221

Related Pictures

Spinsolve Benchtop NMR system at the BAM name 2 2 2 trifluoroethanol cas 75 89 8 tweet 2 2 2 trifluoroethanol d3 100 % PhI(OAc)2, LiOAc, 2,2,2-trifluoroethanol Trifluoroetanol (Trifluoroetil Alcohol) 2000px-2,2,2-trifluoroethanol.svg.png Image of 2,2,2-trifluoroethanol Trifluoroethanol; Trifluoroethyl Alcohol

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関連記事	「trifluoroethanol」

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2,2,2-Trifluoroethanol
Identifiers
CAS number	75-89-8
PubChem	6409
ChemSpider	21106169
DrugBank	DB03226
ChEBI	CHEBI:42330
ChEMBL	CHEMBL116675
Jmol-3D images	Image 1; Image 2
	SMILES OCC(F)(F)F FC(F)(F)CO ;
	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 ;
Properties
Molecular 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
Boiling point	74.0 °C
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 molar; entropy So298	? J.K−1.mol−1
Std enthalpy of; formation ΔfHo298	? kJ/mol
Std enthalpy of; combustion ΔcHo298	-886.6 kJ/mol
Hazards
EU classification	Harmful (Xn)
R-phrases	R10, R20/21/22, R36/38, R62
S-phrases	S16, S36/37/39, S45
NFPA 704	3 2 1
Related compounds
Related alcohols	Hexafluoro-2-propanol
Related compounds	1,1,1-Trifluoroethane; Trifluoroacetic acid
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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2,2,2-trifluoroethanol

関: トリフルオロエタノール

「trifluoroethanol」

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トリフルオロエタノール

関: 2,2,2-trifluoroethanol、TFE

[Gunt-1] Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, 2007.

[2] Bégué, J.-P.; 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, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". Synthesis (Review) 2007 (19): 2925–2943. doi:10.1055/s-2007-983902.

[4] Kabayadi S. Ravikumar, Venkitasamy Kesavan, Benoit Crousse, Danièle Bonnet-Delpon, and Jean-Pierre Bégué (2003), "Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyle Phenyl Sulfoxide", Org. Synth. 80: 184

[5] Sciencelab MSDS

[6] Fischer Scientific MSDS

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2,2,2-trifluoroethanol