N,O-BIS(TRIMETHYLSILYL)ACETAMIDE

Product Code: SIB1846.0
CAS No: 10416-59-8
SDS Sheets: EU | US
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10416-59-8
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2 kg
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13 kg
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150 kg
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Prices listed are EXW price (Morrisville, PA US) in USD. Prices vary depending on currency and Incoterms.

Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    233-892-7
  • Synonyms

    BSA
  • HMIS

    3-2-1-X
  • Molecular Formula

    C8H21NOSi2
  • Molecular Weight (g/mol)

    203.43
  • Purity (%)

    95%
  • TSCA

    Yes
  • Boiling Point (˚C/mmHg)

    71-73/35
  • Density (g/mL)

    0.832
  • Flash Point (˚C)

    42 °C
  • Melting Point (˚C)

    -24°
  • Refractive Index @ 20˚C

    1.418

Additional Properties

  • Hydrolytic Sensitivity

    7: reacts slowly with moisture/water

    • Application

    Review of synthetic utility.1

    Fieser

    F&F: Vol. 13, p 34; Vol. 16, p 285; Vol. 20, p 50; Vol. 21, p 62.

    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. 58-72.

    Safety

  • Hazard Info

    oral rat, LD50: 1,580 mg/kg
  • Packaging Under

    Nitrogen

    • Trimethylsilyl 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.

    Bis(Trimethylsilyl)acetamide; N,O-Bis(trimethylsilyl)acetamide; Trimethylsilyl-N-Trimethylsilylacetamidate; BSA

  • More reactive than SIH6110.0
  • Releases neutral acetamide upon reaction
  • Both silyl groups used
  • Used for silylation in analytical applications
  • Reactions catalyzed by acid
  • Forms enol silyl ethers in ionic liquids
  • Nafion SAC-13 has been shown to be a recyclable catalyst for the trimethylsilylation of primary, secondary, and tertiary alcohols in excellent yields and short reaction times
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure