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

B21127 Triisopropylsilyl trifluoromethanesulfonate, 97%

Codice CAS
80522-42-5
Sinonimi
TIPS-OTf
Trifluoromethanesulfonic acid triisopropylsilyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
5g 35,43
25g 114,33
100g 416,12
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Triisopropylsilyl trifluoromethanesulfonate, 97%

MDL
MFCD00009913
EINECS
000-000-0

Proprietà chimiche

Formula
CF3SO3Si[CH(CH3)2]3
Peso formula
306.42
Punto di ebollizione
45-46°/0.03mm
Punto di infiammabilità
100°(212°F)
Densità
1.136
Indice di rifrazione
1.4150
Sensibilità
Moisture Sensitive
Solubilità
Miscible with chloroform and ethyl acetate.

Applicazioni

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.

Note

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.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H314-H318

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

Dichiarazioni precauzionali: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

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. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
3591541
Classe di rischio
8
Gruppo di imballaggio
II
Codice tariffe armonizzato
2931.90
TSCA
No

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