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Sodium trimethylsiloxide

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Sodium trimethylsiloxide
Names
Other names Sodium trimethylsilanoate, Sodium trimethylsilanolate
Identifiers
CAS Number
ECHA InfoCard 100.038.112 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
Properties
Chemical formula C3H9NaOSi
Molar mass 112.179 g·mol
Appearance white solid
Density 1.255 g/cm
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 , 100 kPa). Infobox references
Chemical compound

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

The salt is used to prepare trimethylsiloxide complexes by salt metathesis. Trimethylsiloxide is a lipophilic pseudohalide.

It is a source of oxide dianion.

Related compounds

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

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, (η-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 () and Hexachloro-μ-oxodiferrate () 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". 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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