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27607-77-8 - Trimethylsilyl trifluoromethanesulfonate, 99% - TMS-OTf - Trifluoromethanesulfonic acid trimethylsilyl ester - A12535 - Alfa Aesar

A12535 Trimethylsilyl trifluoromethanesulfonate, 99%

Numéro de CAS
27607-77-8
Synonymes
TMS-OTf
Trifluoromethanesulfonic acid trimethylsilyl ester

Conditionnement Prix ($) Quantité Disponibilité
10g 32,20
50g 109,00
250g 436,00
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Trimethylsilyl trifluoromethanesulfonate, 99%

MDL
MFCD00000406
EINECS
248-565-4

Propriétés chimiques

Formule
(CH3)3SiSO3CF3
Poids moleculaire
222.26
Point d'ébullition
39-40°/12mm
Point d'éclair
25°(77°F)
Densité
1.225
Indice de réfraction
1.3600
Sensibilité
Moisture Sensitive
Solubilité
Miscible with aliphatic, aromatic hydrocarbons, haloalkanes and ethers. Immiscible with water.

Applications

Trimethylsilyl trifluoromethanesulfonate is used to prepare powerful Lewis acid, difluoroboron triflate etherate in acetonitrile solvent. It is also used as a reagent in a Dieckmann-like cyclization of ester-imides and diesters. Further, it is used in the conversion of carbonyl compounds to their enol ethers. It is also employed for chemical glycosylation reactions. Its reactivity is similar to trimethylsilyl chloride and is also involved in organic synthesis.

Notes

Moisture and air sensitive. Store in a cool place. Incompatible with strong oxidizing agents and strong bases.

Références bibliographiques

Trialkylsilyl perfluoroalkanesulfonates are highly reactive silylating agents (see Appendix 4) and Lewis acids: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).

Amides can be N,O-disilylated with TMSOTf: Org. Synth. Coll., 9, 516 (1998). For conversion of carbonyl compounds to silyl enol ethers, see, e.g.: J. Org. Chem., 58, 1449 (1993); Org. Synth. Coll., 9, 548 (1998). The reaction rate in triethylamine is almost 109 times faster than with TMS chloride: Liebigs Ann. Chem., 1718 (1980).

In general, TMSOTf has a much greater tendency to give C-silylation than TMS chloride. With esters C-silylation usually predominates: Synthesis, 867 (1977); Liebigs Ann. Chem., 816 (1983). Nitriles are C-silylated: Synthesis, 636 (1977); Synth. Commun., 18, 2111 (1988). Electron-rich alkenes, e.g. ketene acetals, as well as electron-rich aromatics such as indoles and pyrroles also undergo C-silylation: Synthesis, 928, 929 (1984):

tert-Butyl esters are cleaved directly to trimethylsilyl esters. Benzyl esters are unaffected, permitting selective cleavage: Synthesis, 545 (1980).

TMSOTf has numerous applications as a Lewis acid catalyst, notably in mediating, under very mild conditions, crossed aldol condensations between silyl enol ethers and acetals: J. Am. Chem. Soc., 102, 3248 (1980); Tetrahedron, 44, 4259 (1988); Org. Synth. Coll., 9, 642 (1998).

For a brief feature on uses of the reagent, see: Synlett, 1940 (2003).

Downey, C. W.; Poff, C. D.; Nizinski, A. N. Friedel-Crafts hydroxyalkylation of indoles mediated by trimethylsilyl trifluoromethanesulfonate. J. Org. Chem. 2015, 80 (20), 10364-10369.

Kendale, J. C.; Valentin, E. M.; Woerpel, K. A. Solvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C-and O-Glycosylations. Org. Lett. 2014, 16 (14), 3684-3687.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H226-H314-H318

Flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.

Mentions de prudence: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,9719
Beilstein
1868911
Classe de danger
3
Groupe d'emballage
III
Code tarifaire harmonisé
2931.90
TSCA
Yes

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Catalyseurs

Analytique et matériel de laboratoire