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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.
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(triphenylphosphine)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).
Gefahrenhinweise (EU): H225-H319-H317-H335
Highly flammable liquid and vapour. Causes serious eye irritation. May cause an allergic skin reaction. May cause respiratory irritation.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.