関: 2,2,2-trifluoroethanol、TFE

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/28 10:29:24」(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; 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

Substitutions mimicking deimination and phosphorylation of 18.5-kDa myelin basic protein exert local structural effects that subtly influence its global folding.

Vassall KA1, Bamm VV1, Jenkins AD1, Velte CJ2, Kattnig DR3, Boggs JM4, Hinderberger D3, Harauz G5.
Biochimica et biophysica acta.Biochim Biophys Acta.2016 Jun;1858(6):1262-77. doi: 10.1016/j.bbamem.2016.02.024. Epub 2016 Feb 19.
Intrinsically-disordered proteins (IDPs) present a complex interplay of conformational variability and multifunctionality, modulated by environment and post-translational modifications. The 18.5-kDa myelin basic protein (MBP) is essential to the formation of the myelin sheath of the central nervous
PMID 26903219

Structural characterization of NRAS isoform 5.

Markowitz J1,2, Mal TK3, Yuan C3, Courtney NB2, Patel M2, Stiff AR2, Blachly J2, Walker C2, Eisfeld AK2, de la Chapelle A2, Carson WE 3rd2,4.
Protein science : a publication of the Protein Society.Protein Sci.2016 May;25(5):1069-74. doi: 10.1002/pro.2916. Epub 2016 Mar 24.
It was recently discovered that the NRAS isoform 5 (20 amino acids) is expressed in melanoma and results in a more aggressive cell phenotype. This novel isoform is responsible for increased phosphorylation of downstream targets such as AKT, MEK, and ERK as well as increased cellular proliferation. T
PMID 26947772

Co-fibrillogenesis of Wild-type and D76N β2-Microglobulin: THE CRUCIAL ROLE OF FIBRILLAR SEEDS.

Natalello A1, Mangione PP2, Giorgetti S3, Porcari R4, Marchese L3, Zorzoli I5, Relini A6, Ami D1, Faravelli G3, Valli M3, Stoppini M3, Doglia SM1, Bellotti V2, Raimondi S7.
The Journal of biological chemistry.J Biol Chem.2016 Apr 29;291(18):9678-89. doi: 10.1074/jbc.M116.720573. Epub 2016 Feb 26.
The amyloidogenic variant of β2-microglobulin, D76N, can readily convert into genuine fibrils under physiological conditions and primes in vitro the fibrillogenesis of the wild-type β2-microglobulin. By Fourier transformed infrared spectroscopy, we have demonstrated that the amyloid transformation
PMID 26921323

Japanese Journal

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, 2012-09-00
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

A facile synthesis of 2-substituted 2,3-dihydro-4(1H)-azuleno〔1,2-d〕pyrimidinones

Wang Dao-Lin,Li Yuan-Feng,Xu Jiao [他]
Heterocycles 83(2), 365-370, 2011-02-01
NAID 40017445172

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リンク元	「TFE」「トリフルオロエタノール」
拡張検索	「2,2,2-trifluoroethanol」

「TFE」

2,2,2-Trifluoroethanol
Identifiers
CAS Number	75-89-8
ChEBI	CHEBI:42330
ChEMBL	ChEMBL116675
ChemSpider	21106169
DrugBank	DB03226
Jmol 3D model	Interactive image; Interactive image
PubChem	6409
	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 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 (DSD)	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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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トリフルオロエタノール、トリテトラフルオロエチレン

関: polytetrafluoroethylene、Teflon、trifluoroethanol

「トリフルオロエタノール」

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英: trifluoroethanol、TFE
関: トリテトラフルオロエチレン、2,2,2-トリフルオロエタノール

「2,2,2-trifluoroethanol」

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2

関: trifluoroethanol

[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; 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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trifluoroethanol