COMMERCIAL
18162-48-6

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t-BUTYLDIMETHYLCHLOROSILANE

Product Code: SIB1935.0

Cas No: 18162-48-6

R&D quantities:

2 kg
$832.00
100 g
$186.00
25 g
$63.00
Trialkylsilyl 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.

Alkyl Silane - Conventional Surface Bonding

Aliphatic, fluorinated aliphatic or substituted aromatic hydrocarbon substituents are the hydrophobic entities which enable silanes to induce surface hydrophobicity. The organic substitution of the silane must be non-polar. The hydrophobic effect of the organic substitution can be related to the free energy of transfer of hydrocarbon molecules from an aqueous phase to a homogeneous hydrocarbon phase. A successful hydrophobic coating must eliminate or mitigate hydrogen bonding and shield polar surfaces from interaction with water by creating a non-polar interphase. Although silane and silicone derived coatings are in general the most hydrophobic, they maintain a high degree of permeability to water vapor. This allows coatings to breathe and reduce deterioration at the coating interface associated with entrapped water. Since ions are not transported through non-polar silane and silicone coatings, they offer protection to composite structures ranging from pigmented coatings to rebar reinforced concrete. A selection guide for hydrophobic silanes can be found on pages 22-31 of the Hydrophobicity, Hydrophilicity and Silane Surface Modification brochure.

tert-Butyldimethylchlorosilane; TBS-Cl; Chlorodimethyl-t-butylsilane; tert-Butylchlorodimethylsilane; Chloro(1,1-dimethylethyl)dimethylsilane
  • Excellent for 1° and 2° alcohols
  • Silylation catalyzed by imidazole
  • Blocking agent widely used in prostaglandin synthesis
  • Stable to many reagents
  • Can be selectively cleaved in presence of acetate, THP and benzyl ethers among others
  • Used for the protection of alcohols, amines, thiols, lactams, and carboxylic acids
  • Clean NMR characteristics of protecting group
  • Silylation reagent - derivatives resistant to Grignards, alkyl lithium compounds, etc
  • Facile removal with flouride ion sources
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure
  • Boiling Point: 124-6°

    EINECS Number: 242-042-4

    Melting Point: 87-90°

    Molecular Weight: 150.72

    Specific Gravity: 0.830

    Flashpoint: 22°C (72°F)

    HMIS Key: 3-4-1-X

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

    Formula: C6H15ClSi

    TSCA: TSCA

    Fieser: F&F: Vol. 4, p 57, p 176; Vol. 5, p 74; Vol. 6, p 78; Vol. 8, p 58; Vol. 9, p 77; Vol. 10, p 62; Vol. 11, p 88; Vol. 12, p 83.

    Additional Properties: 405
    Silylation reagent - derivatives resistant to Grignards, alkyl lithium compounds, etc.
    Vapor pressure, 100°: 476 mm