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N-(TRIMETHYLSILYL)IMIDAZOLE
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
EINECS Number: 242-040-3
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
TSCA: TSCA
Refractive Index: 1.4756
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 debyeTrimethylsilylation reagent specific to hydroxyl groups