TRIS(TRIMETHYLSILYL)SILANE

Product Code: SIT8724.0
CAS No: 1873-77-4
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Synonyms

    1,1,1,3,3,3-HEXAMETHYL-2-TRIMETHYLSILYLTRISILANE; TTMS
  • HMIS

    2-2-1-X
  • Molecular Formula

    C9H28Si4
  • Molecular Weight (g/mol)

    248.67
  • TSCA

    No
  • Boiling Point (˚C/mmHg)

    82-84/12
  • Density (g/mL)

    0.806
  • Flash Point (˚C)

    55 °C
  • Refractive Index @ 20˚C

    1.489

Additional Properties

  • Hydrolytic Sensitivity

    8: reacts rapidly with moisture, water, protic solvents

    • Application

    Reviews.1,2
    Efficient mediator in organic radical reactions.3
    Initiates addition of alkyl iodides to activated olefins.4
    Initiates and promotes the radical addition of perfluoroalkyl iodides to olefins in water.5
    Hydrosilylates olefins in aqueous systems in presence of azo initiators.6
    Reacts with MeLi to form tris(trimethylsilyl)methyllithium.7
    Reacts with LiOMe to form bis(trimethylsilyl)methyllithium.8

    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. 747-754.
    2. Chatgilialoglu, C. Chem. Eur. J. 2008, 14, 2310.
    3. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
    4. Kishimoto, Y.; Ikariya, T. J. Org. Chem. 2000, 65, 7656.
    5. Barata-Vallejo, S.; Postigo, A. J. Org. Chem. 2010, 75, 6141.
    6. Postigo, A. et al. Organometallics 2009, 28, 3282.
    7. Cook, M. A. et al. J. Organomet. Chem. 1970, 24, 529.
    8. Sakurai, H. et al. Tetrahedron Lett. 1973, 4193.

    Safety

  • Packaging Under

    Nitrogen
  • Store Cold

    • 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.

    Tris(trimethylsilyl)silane; 1,1,1,3,3,3-Hexamethyl-2-trimethylsilyltrisilane; TTMS

  • Oxidizes slowly in contact with air at room temperature
  • Efficient mediator in organic radical reactions
  • Initiates addition of alkyl iodides to activated olefins
  • Initiates and promotes the radical addition of perfluoroalkyl iodides to olefins in water
  • Hydrosilylates olefins in aqueous systems in presence of azo initiators
  • Undergoes exothermic decomposition at >100 °C
  • Radical-based reducing agent for organic halides selenides, xanthates and isocyanides and ketones in high yields
  • Can provide complementary stereoselectivity to tri-n-butyltin hydride in the reduction of gem dihalides
  • Mild reducing agent in nucleoside chemistry
  • 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

    Tetramethyldisiloxane: A Practical Organosilane Reducing Agent – Larson

    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.