Sodium trimethylsiloxide

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]

Sodium trimethylsiloxide
Names
Other names
Sodium trimethylsilanoate, Sodium trimethylsilanolate
Identifiers
ECHA InfoCard 100.038.112
Properties
C3H9NaOSi
Molar mass 112.179 g·mol−1
Appearance white solid
Density 1.255 g/cm3
Melting point 147–150 °C (297–302 °F; 420–423 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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]

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

References
  1. Sommer, L. H.; Pietrusza, E. W.; Whitmore, F. C. (1946). "Properties of the Silicon—Hydroxyl Bond in Trialkylsilanols1". Journal of the American Chemical Society. 68 (11): 2282–2284. doi:10.1021/ja01215a047.
  2. Mehring, Michael; Nolde, Christof; Schürmann, Markus (2004). "Crystallographic Report: A polymorph of Undecasodium Decatrimethylsilanolate Hydroxide:[Na11(OSiMe3)10(OH)]". Applied Organometallic Chemistry. 18 (9): 489–490. doi:10.1002/aoc.684.
  3. Krempner, Clemens (2011). "Role of Siloxides in Transition Metal Chemistry and Homogeneous Catalysis". European Journal of Inorganic Chemistry. 2011 (11): 1689–1698. doi:10.1002/ejic.201100044.
  4. Chisholm, Malcolm H.; Eilerts, Nancy W.; Huffman, John C.; Iyer, Suri S.; Pacold, Martha; Phomphrai, Khamphee (2000). "Polylactide Formation by Achiral and Chiral Magnesium and Zinc Alkoxides, (η3-L)MOR, Where L = Trispyrazolyl- and Trisindazolylborate Ligands". Journal of the American Chemical Society. 122 (48): 11845–11854. doi:10.1021/ja002160g.
  5. Do, Y.; Simhon, E. D.; Holm, R. H. (1983). "Improved Syntheses of Tetrachlorodi-μ-sulfidodiferrate Dianion ([Fe2S2Cl4]2-) and Hexachloro-μ-oxodiferrate2- ([Fe2OCl6]2-) and Oxo/Sulfido Ligand Substitution by Use of Silylsulfide Reagents". Inorg. Chem. 22: 3809-12. doi:10.1021/ic00167a027.
  6. Laganis, E. D.; Chenard, B. L. (1984). "Metal Silanolates: Organic Soluble Equivalents for O−2". Tetrahedron Letters. 25 (51): 5831–5834. doi:10.1016/S0040-4039(01)81697-X.
  7. Delaney, Connor P.; Heyboer, E. M.; Denmark, S. E. (2020). "Anhydrous, Homogeneous, Suzuki-Miyaura Cross-Coupling of Boronic Esters using Potassium Trimethylsilanolate". Organic Syntheses. 97: 245–261. doi:10.15227/orgsyn.097.0245. PMC 7808858. PMID 33456091.
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