COMMERCIAL
6485-79-6

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TRIISOPROPYLSILANE, 98%

Product Code: SIT8385.0

Cas No: 6485-79-6

R&D quantities:

1.5 kg
$1,162.50
100 g
$116.00
25 g
$37.00
Trialkylsilyl Blocking Agent

Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.

Tri-substituted Silane Reducing Agent

Organosilanes are hydrocarbon-like and possess the ability to serve as both ionic and free-radical reducing agents. These reagents and their reaction by-products are safer and more easily handled and disposed than many other reducing agents. The metallic nature of silicon and its low electronegativity relative to hydrogen lead to polarization of the Si-H bond yielding a hydridic hydrogen and a milder reducing agent compared to aluminum-, boron-, and other metal-based hydrides. A summary of some key silane reductions are presented in Table 1 of the Silicon-Based Reducing Agents brochure.

Triisopropylsilane; Triisopropylsilylhydride; TIPS-H
  • Silylates strong acids with loss of hydrogen
  • Silylates 1° alcohols selectively
  • Steric bulk allows for selective silylation of compounds with more than one hydroxyl group
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
  • Very sterically-hindered silane
  • Blocking agent forming derivatives stable in presence of Grignard reagents
  • Selectively silylates primary alcohols in presence of secondary alcohols
  • Used as a cation scavenger in the deprotection of peptides
  • Extensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catalyzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007
  • Boiling Point: 169-70°

    EINECS Number: 613-702-2

    Molecular Weight: 158.36

    Specific Gravity: 0.772

    Flashpoint: 37°C (99°F)

    HMIS Key: 2-3-1-X

    Hydrolytic Sensitivity: 3: reacts with aqueous base

    Formula: C9H22Si

    Purity: 98%

    Refractive Index: 1.4358

    Application: Selectively silylates primary alcohols in presence of secondary alcohols.1

    Reference: 1. Horner, L. et al. J. Organomet. Chem. 1985, 282, 155.

    Additional Properties: Blocking agent forming derivatives stable in presence of Grignard reagents.