Consentement d'utilisation des Cookies

J'accepte Notre site sauvegarde des traceurs textes (cookies) sur votre appareil afin de vous garantir de meilleurs contenus et à des fins de collectes statistiques.Vous pouvez désactiver l'usage des cookies en changeant les paramètres de votre navigateur. En poursuivant votre navigation sur notre site sans changer vos paramètres de navigateur vous nous accordez la permission de conserver des informations sur votre appareil.

69739-34-0 - tert-Butyldimethylsilyl trifluoromethanesulfonate, 98% - tert-Butyldimethylsilyl triflate - TBDMS-OTf - A12174 - Alfa Aesar

A12174 tert-Butyldimethylsilyl trifluoromethanesulfonate, 98%

Numéro CAS
69739-34-0
Synonymes
tert-Butyldimethylsilyl triflate
TBDMS-OTf

Dimensions Prix ($) Quantité Disponibilité
5g 57,60
25g 234,00
Ajouter au panier Ajouter au devis en vrac Afficher l'article

tert-Butyldimethylsilyl trifluoromethanesulfonate, 98%

MDL
MFCD00000405
EINECS
274-102-0

Propriétés chimiques

Formule
C7H15F3O3SSi
Poids formulaire
264.34
Point d'ébullition
65-67°/12mm
Point d'éclair
36°(96°F)
Densité
1.151
Indice de réfraction
1.3860
Sensibilité
Moisture Sensitive
Solubilité
Slightly miscible with chloroform.

Applications

tert-Butyldimethylsilyl trifluoromethanesulfonate is involved in the introduction of a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane used in Cope rearrangement. It is associated with a thiolane and promotes the chalcogenide-Morita-Baylis-Hillman reaction. Further, it is used as a highly reactive silylating agent. In addition to this, it is used to prepare enol silyl ethers by reacting with ketones and lactones.

Notes

Moisture sensitive. Store in a cool place. Incompatible with strong acids.

Références bibliographiques

Powerful silylating agent (see Appendix 4) and Lewis acid; compare tert-Butyl­dimethyl­chlorosilane, A13064 and 3429. Silylation of hindered alcohols can be effected with TBDMS-OTf and 2,6-lutidine, where other reagents are unsuccessful: Tetrahedron Lett., 22, 3455 (1981).

Has been used in a sequence for the conversion of N-Boc to N-Cbz: Tetrahedron Lett., 26, 5543 (1985). For an alternative method for this transformation, see Benzyl­ 2,2,2-trichloroacetimidate, A12387.

Treatment of ɑß-unsaturated esters containing a suitably-placed ketone function with the reagent and triethylamine results in tandem intramolecular Michael-aldol reactions to give cyclobutanone derivatives: J. Am. Chem. Soc., 115, 8107 (1993).

For general reactions of trialkylsilyl perfluoroalkanesulfonates, see Trimethyl­silyl­ trifluoromethanesulfonate, A12535; reviews: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).

Cheng, B.; Trauner, D. A Highly Convergent and Biomimetic Total Synthesis of Portentol. J. Am. Chem. Soc. 2015, 137 (43), 13800-13803.

Florence, G. J.; Wlochal, J. Synthesis of the Originally Proposed Structure of Palmerolide C. Chem. Eur. J 2012, 18 (45), 14250-14254.

Mentions de danger et de prudence du SGH

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

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

Mentions de prudence: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. 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 SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
2370068
Classe de danger
8
Groupe d'emballage
II
Code tarifaire harmonisé
2931.90
TSCA
No

Recommandé

  • A12535

    Trimethylsilyl trifluoromethanesulfonate, 99%
  • A13064

    tert-Butyldimethylchlorosilane, 97%
  • A18012

    Oxalyl chloride, 98%
  • L14477

    Triethylsilyl trifluoromethanesulfonate, 98%
  • 44223

    Zinc bromide, anhydrous, 99.999% (metals basis)

Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux

Catalyseurs

Analytique et matériel de laboratoire