17985-72-7

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1,2-BIS(DIMETHYLSILYL)BENZENE

Product Code: SIB1084.0

Cas No: 17985-72-7

2.5 g
$196.00
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Bridging 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.

1,2-Bis(dimethylsilyl)benzene; Dimethylsilphenylene; BSB
  • Used to protect anilines, amines, and amino acids
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure

    • Specific Gravity: 0.893

    Flashpoint: 71°C (160°F)

    HMIS Key: 2-2-1-X

    Hydrolytic Sensitivity: 3: reacts with aqueous base

    Formula: C10H18Si2

    Refractive Index: 1.511

    Application: Acetylenes undergo dehydrogenative double silylation to yield cyclics.1
    Aldehydes undergo dehydrogenative double silylation to yield disila-2-oxacyclohexanes.2
    Reacts with ?-hydroxycarboxylates with Rh to form lactones.3
    Employed in the high-yield reduction of amides to amines in the presence of other reducible groups.4

    Reference: 1. Tanaka, M. et al. Bull. Soc. Chim. Fr. 1993, 129, 667.
    2. Uchimaru, Y. et al. Organometallics 1992, 11, 2639.
    3. Mukaiyama, T. et al. Chem. Lett. 1997, 2, 18.
    4. Hanada, S. et al. J. Am. Chem. Soc. 2009, 131, 15032.

    Fieser: F&F: Vol. 20, p 40.