COMMERCIAL
18156-74-6

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N-(TRIMETHYLSILYL)IMIDAZOLE

Product Code: SIT8590.0

Cas No: 18156-74-6

R&D quantities:

2 kg
$718.00
100 g
$116.00
25 g
$37.00
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
  • Boiling Point: 99° / 14

    EINECS Number: 242-040-3

    Molecular Weight: 140.26

    Specific Gravity: 0.956

    Flashpoint: 40°C (104°F)

    HMIS Key: 2-3-1-X

    Hydrolytic Sensitivity: 7: reacts slowly with moisture/water

    Formula: C6H12N2Si

    Refractive Index: 1.4756

    TSCA: TSCA

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

    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.

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

    Additional Properties: Dipole moment: 4.64 debye
    pKb: 15.07
    Trimethylsilylation reagent specific to hydroxyl groups