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CAS 1070-89-9

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Sodium bis(trimethylsilyl)amide

Description:
Sodium bis(trimethylsilyl)amide, commonly referred to as NaHM(SiMe3)2, is an organosilicon compound characterized by its strong basicity and nucleophilicity. It is typically encountered as a white to light yellow solid and is highly soluble in non-polar solvents such as hexane and toluene, but insoluble in polar solvents like water. The compound features a sodium cation and a bis(trimethylsilyl)amide anion, which contributes to its reactivity, particularly in deprotonation reactions. Sodium bis(trimethylsilyl)amide is often used as a reagent in organic synthesis, particularly in the formation of carbon-nitrogen bonds and as a strong base in various chemical transformations. It is sensitive to moisture and air, requiring careful handling and storage under inert atmospheres to prevent hydrolysis and degradation. Due to its reactivity, it is important to use appropriate safety measures when working with this compound, as it can react vigorously with water and other protic solvents, releasing trimethylsilanol and potentially hazardous byproducts.
Formula:C6H19NSi2·Na
InChI:InChI=1S/C6H19NSi2.Na/c1-8(2,3)7-9(4,5)6;/h7H,1-6H3;
InChI key:InChIKey=QKNDAUTYSODFJV-UHFFFAOYSA-N
SMILES:N([Si](C)(C)C)[Si](C)(C)C.[Na]
Synonyms:
  • 1,1,1,3,3,3-Hexamethyldisilazane sodium salt
  • 1,1,1-trimethyl-N-(trimethylsilyl)silanamine
  • Bis(trimethylsilyl)amine sodium salt
  • Disilazane, 1,1,1,3,3,3-hexamethyl-, sodium deriv.
  • Hexamethyldisilazane sodium salt
  • Hexamethyldisilazylsodium
  • N,N-Bis(trimethylsilyl)amine sodium salt
  • NaHMDS
  • NaMDS
  • Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, sodium salt
  • See more synonyms
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