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N-(TRIMETHYLSILYL)IMIDAZOLE
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 debyepKb: 15.07Trimethylsilylation reagent specific to hydroxyl groups
Tin Compounds
Silanes
Bulk Metal-Organics and Silanes: Pharmaceutical & Organic Synthesis
Silicon-Based Blocking Agents
Enabling Synthetic Organic Transformations