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TRIS(TRIMETHYLSILYL)METHANE
Boiling Point: 80° / 2
Molecular Weight: 232.59
Specific Gravity: 0.827
Flashpoint: 76°C (169°F)
HMIS Key: 2-2-0-X
Hydrolytic Sensitivity: 1: no significant reaction with aqueous systems
Formula: C10H28Si3
Refractive Index: 1.4640
Application: Review of synthetic utility.1
Sterically demanding "trisyl" group.2,3
Linear, thermally-induced NMR shifts.4
Metalation occurs with MeLi to form tris(trimethylsilyl)methyllithium.5
Reacts with LiOMe to form bis(trimethylsilyl)methyllithium.6
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. 746-747.
2. Cowley, A. Inorg. Synth. 1990, 27, 235.
3. Eaborn, C. et al. J. Organomet. Chem. 1975, 101, C40.
4. Sikorsky, W. et al. Magn. Reson. Chem. 1998, 36, 5118.
5. Cook, M. A. et al. J. Organomet. Chem. 1970, 24, 529.
6. Sakurai, H. et al. Tetrahedron Lett. 1973, 4193.
Fieser: F&F: Vol. 20, p 422.
