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B21127 Triisopropylsilyl trifluoromethanesulfonate, 97%

CAS Number
80522-42-5
Synonyms
TIPS-OTf
Trifluoromethanesulfonic acid triisopropylsilyl ester

Stock No. Size Price ($) Quantity Availability
B21127-06 5g 36.90
B21127-14 25g 118.00
B21127-22 100g 424.00
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Triisopropylsilyl trifluoromethanesulfonate, 97%

MDL
MFCD00009913
EINECS
000-000-0

Chemical Properties

Formula
CF3SO3Si[CH(CH3)2]3
Formula Weight
306.42
Boiling Point
45-46°/0.03mm
Flash Point
100°(212°F)
Density
1.136
Refractive Index
1.4150
Storage & Sensitivity
Moisture Sensitive. Ambient temperatures.
Solubility
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.

Literature References

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 Hazard and Precautionary Statements

Hazard Statements: H314

Causes severe skin burns and eye damage.

Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
3591541
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
No

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