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6485-79-6 - Triisopropylsilane, 98% - TIS - L09585 - Alfa Aesar

L09585 Triisopropylsilane, 98%

CAS Number
6485-79-6
Synonyms
TIS

Triisopropylsilane, 98%

MDL
MFCD00009657

Chemical Properties

Formula
C9H22Si
Formula Weight
158.36
Boiling Point
166°
Flash Point
35°(95°F)
Density
0.773
Refractive Index
1.4340
Solubility
Immiscible with water.

Applications

Triisopropylsilane is used as a protecting group in peptide synthesis and is also used as a reducing agent for the selective reduction of anomeric C-phenyl ketals. It is used in the selective silylation of primary hydroxyl groups without affecting the secondary hydroxyl group. It is used in the preparation of anti-1,2-diols catalyzed by a Ni(O) N-heterocyclic carbine complex with high diastereoselectivity.

Notes

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

Literature References

Selective silylation of primary OH groups in the presence of secondary has been carried out with this reagent in combination with CsF and imidazole: J. Organomet. Chem., 282, 155 (1985). See Appendix 4.

Triethylsilane and triisopropylsilane have been studied as cation scavengers in the deprotection of peptides with TFA, and were found to give good results, with triisopropylsilane being particularly effective in trapping trityl cations in the TFA deprotection of cysteine containing peptides. The use of triisopropylsilane minimizes the risk of reduction of the indole nucleus in tryptophan-containing peptides: Tetrahedron Lett., 30, 2739 (1989). See Appendix 6.

Lee, J. H. Reduction of a 4-pyrrole phenylacyl-containing peptide with trifluoroacetic acid-triisopropylsilane-phenol-H2O during solid-phase peptide synthesis and its protein kinase C alfa inhibitory activity. Bioorg. Med. Chem. Lett. 2005, 15 (9), 2271-2274.

Aihara, K.; Komiya, C.; Shigenaga, A.; Inokuma, T.; Takahashi, D.; Otaka, A. Liquid-Phase Synthesis of Bridged Peptides Using Olefin Metathesis of a Protected Peptide with a Long Aliphatic Chain Anchor. Org. Lett. 2015, 17 (3), 696-699.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H315-H319-H335

Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210-P261-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1733718
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2931.90
TSCA
No

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