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Hexamethyldisilane; HMD; 2,2,3,3-Tetramethyl-2,3-disilabutane
EINECS Number: 215-911-0
Alternative Name: HMD
Specific Gravity: 0.7293
Flashpoint: -1°C (30°F)
HMIS Key: 2-4-0-X
Hydrolytic Sensitivity: 1: no significant reaction with aqueous systems
Refractive Index: 1.4214
Application: Review of synthetic utility.1
Source for trimethylsilyl anion.2,3
Replaces aromatic nitriles with TMS groups in presence of [RhCl(cod)]2.4
Precursor for CVD of silicon carbide.5
Brings about the homocoupling of arenesulfonyl chlorides in the presence of Pd2(dba)3.6
Used as a solvent for the direct borylation of fluoroaromatics.7
Reacts with alkynes to form siloles.8
Undergoes the silylation of acid chlorides to give acylsilanes.9
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. 278-284.
2. Shippey, M. A. et al. J. Org. Chem. 1977, 42, 2654.
3. F&F: Vol. 10, p 96; Vol.11, p 253.
4. Tobisu, M. et al. J. Am. Chem. Soc. 2006, 128, 4152.
5. Thin Solid Films 1999, 252, 13.
6. Kashiwabara, T.; Tanaka, M. Tetrahedron Lett. 2005, 46, 7125.
7. Teltewskoi, M. et al. Angew. Chem., Int. Ed. Engl. 2010, 49, 3947.
8. >Akagawa, K. et al. Synlett 2011, 22, 813.
9. Capperucci, A. et al. J. Org. Chem. 1988, 53, 3612.
Additional Properties: Ionization energy: 8.69 eV?Hcomb: 1,411.7 kcal/mole?Hform (gas): -118 kcal/mole?Hvap: 9.5 kcal/moleRotational barrier, Si-Si: 1.05 kcal/moleEa decomposition at 545°K: 80.5 kcal/mole