TRIISOPROPYLSILANE, 97%

Product Code: SIT8385.0
CAS No: 6485-79-6
SDS Sheets: EU | US
COMMERCIAL
6485-79-6
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25 g
$45.00
100 g
$140.00
1.5 kg
$1,395.00
14 kg
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150 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    464-880-1;613-702-2
  • HMIS

    2-3-1-X
  • Molecular Formula

    C9H22Si
  • Molecular Weight (g/mol)

    158.36
  • Purity (%)

    97%
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    169-170
  • Density (g/mL)

    0.772
  • Flash Point (˚C)

    37 °C
  • Refractive Index @ 20˚C

    1.4358

Additional Properties

  • Hydrolytic Sensitivity

    3: reacts with aqueous base
  • Application

    Selectively silylates primary alcohols in presence of secondary alcohols.1

    Reference

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

    Safety

  • Packaging Under

    Nitrogen
  • 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
  • Silicon Chemistry, Articles

    Key Organosilane Reductions – Larson

    The Si-H bond, based on the relative electrongativities of Si and H, is polarised such that the hydrogen is slightly hydridic in nature. The fact that the silanes are not strongly hydridic makes them excellent candidates for mild and selective reductions of organic functional groups.

    Silicon Chemistry, Articles

    Organosilane Reductions with Polymethylhydrosiloxanes – Larson

    The reduction of a comprehensive range of organic functional groups ranging from carboxylic acids to aryl fluorides have been shown to be possible with a variety of organosilanes. A comprehensive review of the ionic and transition metal-catalyzed reductions of organic functional groups has recently appeared.

    Silicon Chemistry, Articles

    The Synthesis of Gliflozins – Larson

    Some of the general approaches to the key steps in the synthesis of gliflozins, a class of glucose transporters, are discussed. In particular the glycosidation step for the introduction of the key aryl moiety onto the glucose and the reduction steps are presented.  Click here for more product information on tetramethyldisiloxane (TMDO, TMDS) reducing agent.