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

B21127 Triisopropylsilyl trifluoromethanesulfonate, 97%

CAS-Nummer
80522-42-5
Synonyme
TIPS-OTf
Trifluoromethanesulfonic acid triisopropylsilyl ester

Größe Preis ($) Menge Verfügbarkeit
5g 35,10
25g 113,00
100g 412,00
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Triisopropylsilyl trifluoromethanesulfonate, 97%

MDL
MFCD00009913
EINECS
000-000-0

Chemische Eigenschaften

Formel
CF3SO3Si[CH(CH3)2]3
Molmasse
306.42
Siedepunkt
45-46°/0.03mm
Flammpunkt
100°(212°F)
Dichte
1.136
Brechungsindex
1.4150
Sensitivität
Moisture Sensitive
Löslichkeit
Miscible with chloroform and ethyl acetate.

Anwendungen

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.

Bemerkungen

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.

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H314-H318

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

Sicherheitshinweise: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Do not breathe dusts or mists. 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.

Weitere Referenzen

Beilstein
3591541
Gefahrenklasse
8
Verpackungsgruppe
II
Harmonized Tariff Code
2931.90
TSCA
No

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