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75-89-8 - 2,2,2-Trifluoroethanol, 99+% - Trifluoroethyl alcohol - A10788 - Alfa Aesar

A10788 2,2,2-Trifluoroethanol, 99+%

Codice CAS
75-89-8
Sinonimi
Trifluoroethyl alcohol

2,2,2-Trifluoroethanol, 99+%

MDL
MFCD00004672
EINECS
200-913-6

Proprietà chimiche

Formula
C2H3F3O
Peso formula
100.04
Punto di fusione
-44°
Punto di ebollizione
74-75°
Punto di infiammabilità
29°(84°F)
Densità
1.391
Indice di rifrazione
1.2900
Solubilità
Miscible with water, ethers, ketones, alcohols and chloroform.

Applicazioni

Trifluoroethanol serves as a solvent and a raw material in organic chemistry and biology. TFE is a solvent of choice for hydrogen peroxide-mediated oxidations of sulfides. Trifluoroethanol acts as a protein denaturant. It is used in the manufacture of certain pharmaceuticals and drug substances. The drug fluromer, which is 2,2,2-trifluoro-1-vinyloxyethane, is the vinyl ether of trifluorethanol. It is an effective solvent for peptides and proteins, and used for NMR-based protein folding studies, and in the manufacture of nylon. As a source of the trifluoromethyl group, it is employed in several organic reactions, for example in Still-Gennari modification of Horner-Wadsworth-Emmons reaction (HWE) reaction.

Note

Moisture sensitive.

Letteratura

Useful ionizing solvent, see: Tetrahedron Lett., 2335 (1974), and references therein. Good solvent for oligopeptides with potential as a cosolvent along with proton acceptors such as DMF for peptide coupling reactions: Tetrahedron Lett., 33, 7007 (1992). Compare 1,1,1,3,3,3-Hexafluoro-2-propanol, A12747.

Effective solvent for uncatalyzed epoxidations of alkenes with hydrogen peroxide (caution! 60%): Synlett, 248 (2001). For a review of fluorinated alcohols as solvents for selective and clean reactions, see: Synlett, 18 (2004).

Trifluoroethyl esters have also found use as active esters in peptide coupling; see, for example: J. Chem. Soc., Perkin 1, 2867 (1996).

Reacts with triphenylphosphine dibromide to give the bis(trifluoroethoxy)phosphorane, which converts alcohols to trifluoroethyl ethers, carboxylic acids to trifluoroethyl esters and aldehydes to bis(trifluoroethyl) acetals: J. Org. Chem., 45, 5052 (1980).

The stereodirecting effect of the MEM group (see 2-Methoxyethoxymethyl­ chloride, L01050) has been exploited by Percy et al in the formation of a new fluorine-containing acyl anion equivalent: Tetrahedron, 51, 9201 (1995):

Claisen or Wittig rearrangements of the derived difluoroallyl alcohols can be used in routes to molecules containing a CF2 group: Tetrahedron, 51, 11327 (1995); J. Org. Chem., 61, 166 (1996), or to monofluorinated vinylic compounds: Tetrahedron Lett., 37, 5183 (1996).

Bava, Y. B.; Martínez, Y. B.; Betancourt, A. M.; Erben, M. F.; Filho, R. L. C.; Védova, C. O. D.; Romano, R. M. Ionic Fragmentation Mechanisms of 2, 2, 2-Trifluoroethanol Following Excitation with Synchrotron Radiation. 2015, 16 (2), 322-330.

Scodeller, I.; Salvini, A.; Manca, G.; Ienco, A.; Luconi, L.; Oberhauser, W. 2,2,2-Trifluoroethanol-assisted imine hydrogenation by a Ru-monohydride. 2015, 431, 242-247.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H301-H311-H332-H315-H335-H318-H226

Toxic if swallowed. Toxic in contact with skin. Harmful if inhaled. Causes skin irritation. May cause respiratory irritation. Causes serious eye damage. Flammable liquid and vapour.

Dichiarazioni precauzionali: P210-P261-P280-P301+P310-P303+P361+P353-P305+P351+P338-P361-P304+P340-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
1733203
Classe di rischio
3
Gruppo di imballaggio
III
Codice tariffe armonizzato
2905.59
TSCA
Yes
RTECS
KM5250000

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