Sodium trimethylsiloxide explained

Sodium trimethylsiloxide is an organosilicon compound with the formula NaOSi(CH₃)₃. It is the sodium salt of the conjugate base derived from trimethylsilanol.^[1] A white solid, its molecular structure consists of a cluster with Na-O-Na linkages on the basis of closely related compounds.^[2]

The salt is used to prepare trimethylsiloxide complexes by salt metathesis. Trimethylsiloxide is a lipophilic pseudohalide.^{[3] [4]}

It is a source of oxide dianion.^{[5] [6]}

Related compounds

• Sodium silox, NaOSi(tBu)₃    (tBu = C(CH₃)₃)
• Potassium trimethylsilanolate^[7]

References

1. 10.1021/ja01215a047. Properties of the Silicon—Hydroxyl Bond in Trialkylsilanols1. 1946. Sommer. L. H.. Pietrusza. E. W.. Whitmore. F. C.. Journal of the American Chemical Society. 68. 11. 2282–2284.
2. 10.1002/aoc.684. Crystallographic Report: A polymorph of Undecasodium Decatrimethylsilanolate Hydroxide:[Na₁₁(OSiMe₃)₁₀(OH)]. 2004. Mehring. Michael. Nolde. Christof. Schürmann. Markus. Applied Organometallic Chemistry. 18. 9. 489–490.
3. 10.1002/ejic.201100044. Role of Siloxides in Transition Metal Chemistry and Homogeneous Catalysis. 2011. Krempner. Clemens. European Journal of Inorganic Chemistry. 2011. 11. 1689–1698.
4. 10.1021/ja002160g. Polylactide Formation by Achiral and Chiral Magnesium and Zinc Alkoxides, (η³-L)MOR, Where L = Trispyrazolyl- and Trisindazolylborate Ligands. 2000. Chisholm. Malcolm H.. Eilerts. Nancy W.. Huffman. John C.. Iyer. Suri S.. Pacold. Martha. Phomphrai. Khamphee. Journal of the American Chemical Society. 122. 48. 11845–11854.
5. Do. Y.. Simhon. E. D.. Holm. R. H.. Improved Syntheses of Tetrachlorodi-μ-sulfidodiferrate Dianion ([Fe₂S₂Cl₄]^2-) and Hexachloro-μ-oxodiferrate^2- ([Fe₂OCl₆]^2-) and Oxo/Sulfido Ligand Substitution by Use of Silylsulfide Reagents. Inorg. Chem.. 1983. 22. 3809-12. 10.1021/ic00167a027.
6. 10.1016/S0040-4039(01)81697-X. Metal Silanolates: Organic Soluble Equivalents for O⁻². 1984. Laganis. E. D.. Chenard. B. L.. Tetrahedron Letters. 25. 51. 5831–5834.
7. 10.15227/orgsyn.097.0245. Anhydrous, Homogeneous, Suzuki-Miyaura Cross-Coupling of Boronic Esters using Potassium Trimethylsilanolate. 2020. Delaney. Connor P.. Heyboer. E. M.. Denmark. S. E.. Organic Syntheses. 97. 245–261. 33456091. 7808858.