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80522-42-5 - Triisopropylsilyl trifluoromethanesulfonate, 97% - TIPS-OTf - Trifluoromethanesulfonic acid triisopropylsilyl ester - B21127 - Alfa Aesar

B21127 Triisopropylsilyl trifluoromethanesulfonate, 97%

Numéro de CAS
80522-42-5
Synonymes
TIPS-OTf
Trifluoromethanesulfonic acid triisopropylsilyl ester

Conditionnement Prix ($) Quantité Disponibilité
5g 35,10
25g 113,00
100g 412,00
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Triisopropylsilyl trifluoromethanesulfonate, 97%

MDL
MFCD00009913
EINECS
000-000-0

Propriétés chimiques

Formule
CF3SO3Si[CH(CH3)2]3
Poids moleculaire
306.42
Point d'ébullition
45-46°/0.03mm
Point d'éclair
100°(212°F)
Densité
1.136
Indice de réfraction
1.4150
Sensibilité
Moisture Sensitive
Solubilité
Miscible with chloroform and ethyl acetate.

Applications

Triisopropylsilyl trifluoromethanesulfonate is used as a reagent for the introduction of triisopropylsilyl(TIPS) group in organic synthesis. It is involved in the synthesis of 2-substituted benzothiopyran-4-ones and silyloxy acetylenes. As a protecting group in organic synthesis, it is utilized especially for the protection of primary amines. Furthermore, it plays an important role in Takahashi Taxol total synthesis or for chemical glycosylation reactions.

Notes

Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong bases and strong oxidizing agents. Hydrolyzes in water.

Références bibliographiques

Reagent for introduction of the triisopropylsilyl (TIPS) group: Tetrahedron Lett., 22, 3455 (1981); compare Chlorotriisopropyl­silane, A17376, and Appendix 4. For general reactions of silyl triflates, see Trimethyl­silyl­ trifluoromethanesulfonate, A12535.

For use in the synthesis of 2-substituted benzothiopyran-4-ones, see: Synlett, 182 (1996):

A method for protecting both H atoms of a primary amine consists of formation of the succinimide, followed by enolsilylation with TIPS-OTf, to form the 2,5-bis(triisopropylsiloxy)pyrroles. Deprotection can be effected by desilylation with dilute HCl, followed by hydrazinolysis: Tetrahedron Lett., 38, 2617 (1997).

For a comprehensive review of the TIPS group in organic chemistry, see: Chem. Rev., 95, 1009 (1995).

Hayashi, Y.; Yamazaki, T.; Nakanishi, Y.; Ono, T.; Taniguchi, T.; Monde, K.; Uchimaru, T. Asymmetric Nitrocyclopropanation of alfa-Substituted alfa, beta-Enals Catalyzed by Diphenylprolinol Silyl Ether for the Construction of All-Carbon Quaternary Stereogenic Centers. Eur. J. Org. Chem. 2015, 2015 (26), 5747-5754.

Chang, J. C.; Lai, C. C.; Chiu, S. H. A Redox-Controllable Molecular Switch Based on Weak Recognition of BPX26C6 at a Diphenylurea Station. Molecules 2015, 20 (2), 1775-1787.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Mentions de prudence: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
3591541
Classe de danger
8
Groupe d'emballage
II
Code tarifaire harmonisé
2931.90
TSCA
No

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