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58479-61-1

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t-BUTYLDIPHENYLCHLOROSILANE

Product Code: SIB1968.0

Cas No: 58479-61-1

R&D quantities:

10 g
$37.00
50 g
$143.00
750 g
$993.00
2 kg
$1,756.00
Phenyl-Containing 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.

tert-Butyldiphenylchlorosilane; (1,1-Dimethylethyl)diphenylchlorosilane; tert-Butylchlorodiphenylsilane
  • Forms more stable ethers than TBS ethers
  • Used to protect phenols, amines, carboxylic acids, and amides
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
  • Boiling Point: 90° / 0.015

    EINECS Number: 261-282-0

    Molecular Weight: 274.87

    Specific Gravity: 1.074

    Flashpoint: 112°C (234°F)

    HMIS Key: 3-1-0-X

    Hydrolytic Sensitivity: 7: reacts slowly with moisture/water

    Formula: C16H19ClSi

    Refractive Index: 1.5680

    TSCA: TSCA

    Application: Review of synthetic utility.1
    Due to steric bulk can be converted to ?-silyl aldehydes,2 which can be converted to olefins with high stereoselectivity.3

    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. 135-138.
    2. Barbero, A. et al. J. Chem. Soc., Perkin Trans 1 1995, 1525.
    3. Barbero, A. et al. Synthesis 2000, 1223.

    Fieser: F&F: Vol. 6, p 81; Vol. 12, p 81.

    Additional Properties: Blocking agent
    Vapor pressure, 100°: 0.02 mm