COMMERCIAL
3277-26-7

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1,1,3,3-TETRAMETHYLDISILOXANE, 98%

Product Code: SIT7546.0

Cas No: 3277-26-7

R&D quantities:

1.5 kg
$324.00
250 g
$146.00
25 g
$21.00
Alkenylsilane Cross-Coupling Agent

The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.

ALD Material

Atomic layer deposition (ALD) is a chemically self-limiting deposition technique that is based on the sequential use of a gaseous chemical process. A thin film (as fine as -0.1 Å per cycle) results from repeating the deposition sequence as many times as needed to reach a certain thickness. The major characteristic of the films is the resulting conformality and the controlled deposition manner. Precursor selection is key in ALD processes, namely finding molecules which will have enough reactivity to produce the desired films yet are stable enough to be handled and safely delivered to the reaction chamber.

Siloxane-Based 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.

1,1,3,3-Tetramethyldisiloxane; 1,1-Dihydro-1,1,3,3-tetramethyldisiloxane; TMDO; TMDS
  • Viscosity, 20 °C: 0.56 cSt
  • ΔHcomb: 4,383 kJ/mol
  • ΔHvap: 30.3 kJ/mol
  • Vapor pressure, 27 °C: 194.8 mm
  • Reduces aromatic aldehydes to benzyl halides
  • Employed in reductive halogenation of aldehydes and epoxides
  • Used to link ferrocenylsilane, polyolefin block copolymers into stable cylindrical forms
  • Endcapper for polymerization of hydride terminated silicones
  • Organic reducing agent
  • Employed in high-yield reduction of amides to amines in the presence of other reducible groups
  • Reduces anisoles to arenes
  • Hydrosilylates terminal alkynes to form alkenylsilanes capable of cross-coupling with aryl and vinyl halides
  • Extensive review of silicon based reducing agents: Larson, G.; Fry, J. L. "Ionic and Organometallic-Catalyzed Organosilane Reductions", Wipf, P., Ed.; Wiley, 2007
  • Extensive review of silicon based cross-coupling agents: Denmark, S. E. et al. "Organic Reactions, Volume 75" Denmark, S. E. ed., John Wiley and Sons, 233, 2011
  • Boiling Point: 70-1°

    EINECS Number: 221-906-4

    Molecular Weight: 134.33

    Specific Gravity: 0.757

    Flashpoint: -12°C (10°F)

    HMIS Key: 2-4-1-X

    Hydrolytic Sensitivity: 3: reacts with aqueous base

    Formula: C4H14OSi2

    Refractive Index: 1.3669

    TSCA: TSCA

    Application: Employed in reductive halogenation of aldehydes and epoxides.1
    Used to link ferrocenylsilane, polyolefin block copolymers into stable cylindrical forms.2
    Employed in the high-yield reduction of amides to amines in the presence of other reducible groups.3
    Reduces anisoles to arenes.4
    Hydrosilylates terminal alkynes to form alkenylsilanes capable of cross-coupling w/ aryl and vinyl halides.5
    Employed in the reduction of an acetopheone derivative to the methylene in the synthesis of ziprasidone.6

    Reference: 1. Azipura et al. Tetrahedron Lett. 1984, 25, 3123.
    2. Wang, X.-S. et al. J. Am. Chem. Soc. 2003, 125, 12686.
    3. Hanada, S. et al. J. Am. Chem. Soc. 2009, 131, 15032.
    4. Alvarez-Bercedo, P.; Martin, R. J. Am. Chem. Soc. 2010, 132, 17352.
    5. Denmark, S. E.; Wang, Z. Org. Lett. 2001, 3, 1073.
    6. Nadkami, D.; Hallissey, J. F. Org. Proc. Res. Dev. 2008, 12, 1142.

    Additional Properties: 208
    ?Hcomb: 1,047 kcal/mole
    ?Hvap: 7.25 kcal/mole
    Endcapper for polymerization of hydride terminated silicones
    Vapor pressure, 27°: 194.8 mm