N-(TRIMETHYLSILYL)IMIDAZOLE

Product Code: SIT8590.0
CAS No: 18156-74-6
SDS Sheets: EU | US
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18156-74-6
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25 g
$45.00
100 g
$140.00
750 g
$423.00
2 kg
$862.00
14 kg
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175 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    242-040-3
  • HMIS

    2-3-1-X
  • Molecular Formula

    C6H12N2Si
  • Molecular Weight (g/mol)

    140.26
  • Purity (%)

    97%
  • TSCA

    Yes
  • Boiling Point (˚C/mmHg)

    99/14
  • Density (g/mL)

    0.956
  • Flash Point (˚C)

    40 °C
  • Refractive Index @ 20˚C

    1.4756

Additional Properties

  • Hydrolytic Sensitivity

    7: reacts slowly with moisture/water

    • Application

    Review of synthetic utility.1
    Shown to open an epoxide in a syn fashion.2

    Fieser

    F&F: Vol. 2, p 412; Vol. 3, p 148; Vol. 7, p 399; Vol. 11, p 575.

    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. 640-645.
    2. Adam, W. et al. J. Am. Chem. Soc. 1991, 113, 8005.

    Safety

  • 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.

    Trimethylsilylimidazole; TMSIM; 1-(Trimethylsilyl)imidazole

  • Powerful silylating agent for alcohols
  • Does not react with aliphatic amines
  • 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