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

L09585 Triisopropylsilane, 98%

Numéro CAS
6485-79-6
Synonymes
TIS

Dimensions Prix ($) Quantité Disponibilité
5g 23,20
25g 67,90
100g 205,00
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Triisopropylsilane, 98%

MDL
MFCD00009657

Propriétés chimiques

Formule
C9H22Si
Poids formulaire
158.36
Point d'ébullition
166°
Point d'éclair
35°(95°F)
Densité
0.773
Indice de réfraction
1.4340
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H226-H315-H319-H335

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

Mentions de prudence: P210-P261-P280-P240-P303+P361+P353-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. 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 INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
1733718
Classe de danger
3
Groupe d'emballage
III
Code tarifaire harmonisé
2931.90
TSCA
No

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