Cookies disclaimer

Estoy de acuerdo utilizamos cookies para mejorar la experiencia de navegación del usuario y para estudiar cómo se utiliza nuestro sitio web. si navega por nuestro sitio web, estará aceptando el uso de las cookies en las condiciones establecidas en la presente política de cookies. esta política puede ser actualizada, por lo que le invitamos a revisarla de forma regular

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

B21127 Triisopropylsilyl trifluoromethanesulfonate, 97%

Número CAS
80522-42-5
Nombre Alternativo
TIPS-OTf
Trifluoromethanesulfonic acid triisopropylsilyl ester

Tamaño Precio ($) Cantidad Disponibilidad
5g 35,10
25g 113,00
100g 412,00
Añadir al carrito Añadir al presupuesto al por mayor Ver artículo

Triisopropylsilyl trifluoromethanesulfonate, 97%

MDL
MFCD00009913
EINECS
000-000-0

Propiedades químicas

Fórmula
CF3SO3Si[CH(CH3)2]3
Peso molecular
306.42
Punto de ebullición
45-46°/0.03mm
Punto de inflamabilidad
100°(212°F)
Densidad
1.136
Índice de refracción
1.4150
Sensibilidad
Moisture Sensitive
Solubilidad
Miscible with chloroform and ethyl acetate.

Aplicaciones

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.

Notas

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.

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H314-H318

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

Indicaciones de precaución: 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.

Otras referencias

Beilstein
3591541
Clase de peligro
8
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2931.90
TSCA
No

Recomendado

Visto recientemente

Productos químicos

Ciencias de la vida

Metales & materiales

Catalizadores

Análisis y material de laboratorio