Hexamethyldisilane acts as a silylating reagent for allylic acetates, aryl halides and diketones. It is a source material for vapor deposition during silicon carbide growth. It is also used in electronic and semiconducter industries.
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Applications
Hexamethyldisilane acts as a silylating reagent for allylic acetates, aryl halides and diketones. It is a source material for vapor deposition during silicon carbide growth. It is also used in electronic and semiconducter industries.
Solubility
Insoluble in water. Soluble in alcohol, ether and acetone.
Notes
Stable under recommended storage conditions. Incompatible with oxidizing agents, acids and bases.
RUO – Research Use Only
General References:
- B.Beagley; J.J.Monaghan; T.G.Hewitt. Electron-diffraction studies of tetramethylsilane and hexamethyldisilane, and discussion of the lengths of Si-C bonds. Journal of Molecular Structure. 1971, 8, (4),401-411
- M.Simon; T.Lebrun; R.Martins; G.G.B. de Souza; I.Nenner; M.Lavollee; P.Morin. Multicoincidence mass spectrometry applied to hexamethyldisilane excited around the silicon 2p edge. J. Phys. Chem. 1993, 97, (20),5228-5237
- Precursor of TMSLi, TMSNa and TMSK by cleavage with alkyllithiums or alkoxides. Reaction of the metallated derivatives with aryl halides gives aryltrimethylsilanes: J. Org. Chem., 42, 2654 (1977). The anion adds 1,4-to ɑß-enones to give ß-silyl ketones: J. Org. Chem., 41, 3063 (1976); Tetrahedron Lett., 24, 3497 (1983). The anion may also be used to deoxygenate secondary nitroalkanes (to ketoximes), nitrones (to imines), and heterocyclic N-oxides: J. Org. Chem., 64, 2211 (1999).
- Also cleaved by TBAF to give the salt-free silyl anion, which adds to aldehydes to give, after acid hydrolysis, ɑ-hydroxy silanes: J. Org. Chem., 48, 912 (1983). TBAF also catalyzes the silylation of OH groups under very mild conditions: Tetrahedron Lett., 35, 8413 (1994). See Appendix 4.
- Couples with aryl, benzyl or allyl halides in the presence of Tetrakis(triphenyl phosphine) palladium(0) , 10548, to give the corresponding silanes: J. Organomet. Chem., 148, 97 (1978); 225, 331 (1982).
- Aryl and alkenyl nitriles undergo ipso-silylation-decyanation, catalyzed by Chloro(1,5-cyclooctadiene) rhodium(I) dimer, 10466, to give the corresponding trimethylsiliyl derivatives: J. Am. Chem. Soc., 128, 8152 (2006).