DIISOPROPYLCHLOROSILANE

Product Code: SID3535.0
CAS No: 2227-29-4
SDS Sheets: EU | US
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Quantity
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5 g
$66.00
25 g
$264.00
750 g
$2,865.00
2 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • HMIS

    3-4-1-X
  • Molecular Formula

    C6H15ClSi
  • Molecular Weight (g/mol)

    150.72
  • Purity (%)

    97%
  • TSCA

    Yes
  • Boiling Point (˚C/mmHg)

    137°
  • Density (g/mL)

    0.872
  • Flash Point (˚C)

    22 °C
  • Refractive Index @ 20˚C

    1.4278

Additional Properties

  • Hydrolytic Sensitivity

    8: reacts rapidly with moisture, water, protic solvents
  • Application

    Review of synthetic utility.1
    Reduces ?-hydroxyketones stereoselectively.2
    Used in the tethered reactions of unsaturated alcohols.3
    Used in the silicon-based cross-coupling of vinyl ethers with aryl iodides.4

    Reference

    1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 151-156.
    2. Anwar, S. et al. Chem. Comm. 1986, 831.
    3. Robertson, J. et al. Tetrahedron Lett. 1998, 39, 669.
    4. Evans, P. A.; Baum, E. W. J. Am. Chem. Soc. 2004, 126, 11150.

    Safety

  • Packaging Under

    Nitrogen
  • Specialty Silicon-Based 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.

    Diisopropylchlorosilane; Chlorodiisopropylsilane; Chlorobis(1-methylethyl)silane

  • Silylates and reduces β-hydroxy ketones selectively
  • Reduces β-hydroxyketones stereoselectively
  • Used in a silylation-reduction-allylation sequence of β-hydroxy esters to homoallylic-substituted 1,3-diols
  • Used in the silylation-hydrosilation-oxidation of allyl alcohols to 1,3-diols
  • Reaction carried out in diastereoselective manner
  • Photochemically removable
  • Reduces β-hydroxy ketones to anti-1,3 diols
  • Used in the tethered reactions of unsaturated alcohols
  • Used in the silicon-based cross-coupling of vinyl ethers with aryl iodides
  • Extensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catalyzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
  • 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.