18395-90-9

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DI-t-BUTYLDICHLOROSILANE

Product Code: SID3205.0

Cas No: 18395-90-9

R&D quantities:

25 g
$660.00
5 g
$165.00
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.

Di-tert-butyldichlorosilane; Bis(1,1-dimethylethyl)dichlorosilane; Dichlorobis(1,1-dimethylethyl)silane; DTBS
  • Used to protect 1,2-diols, and 1,3- diols
  • Forms 4,6-cyclic di-tert-butylsilylenediyl ethers with glycopyranosides
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
  • Boiling Point: 190-1°

    EINECS Number: 242-273-0

    Melting Point: -15°

    Molecular Weight: 213.22

    Specific Gravity: 1.009

    Flashpoint: 61°C (142°F)

    HMIS Key: 3-2-1-X

    Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents

    Formula: C8H18Cl2Si

    Refractive Index: 1.4561

    TSCA: TSCA

    Application: Review of synthetic utility.1
    Reagent for protection of 1,2 and 1,3 diols.2
    Used as the source for di-tert-butylsilylene, in particular for the thermal silylene precursor, 1-silabicyclo[4.2.0]heptane.3 The silabicycloheptane di-tert-butylsilylene precursor has been utilized in a number of synthetic applications.4,5,6

    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. 201-207.
    2. Trost, B. et al. Tetrahedron Lett. 1981, 22, 4999.
    3. Driver, T. G.; Franz, A. K.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 6524.
    4. Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2004, 126, 9993.
    5. Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2003, 125, 10659.
    6. Howard, B. E.; Woerpel, K. A. Org. Lett. 2007, 9, 4651.