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Sodium bis(trimethylsilyl)amide

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Sodium bis(trimethylsilyl)amide Basic information
Sodium bis(trimethylsilyl)amide Chemical Properties
  • Melting point:171-175 °C (lit.)
  • Boiling point:67°C
  • Density 0.904 g/mL at 25 °C
  • Flash point:43 °F
  • storage temp. 2-8°C
  • solubility Soluble in hexane, toluene, ether,terahydrofuran, benzene and toluene.
  • form Liquid
  • Specific Gravity0.9
  • color Clear orange to brown
  • Water Solubility reacts
  • Sensitive Moisture Sensitive
  • Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
  • BRN 3629917
  • CAS DataBase Reference1070-89-9(CAS DataBase Reference)
  • EPA Substance Registry SystemSilanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, sodium salt (1070-89-9)
Safety Information
MSDS
Sodium bis(trimethylsilyl)amide Usage And Synthesis
  • Chemical PropertiesSlightly yellow to light beige crystalline powder
  • Physical propertiesmp 171–175 °C; bp 170 °C/2 mmHg.
  • UsesSodium bis(trimethylsilyl)amide is a synthetically useful reagent in that it combines both high basicity and nucleophilicity, each of which may be exploited for useful organic transformations such as selective formation of enolates, preparation of Wittig reagents, formation of acyl anion equivalents, and the generation of carbenoid species. As a nucleophile, it has been used as a nitrogen source for the preparation of primary amines.It is useful as a sterically hindered base and as a nucleophile.
  • UsesIt is a strong base; deprotonates ketones and esters to generate enolate derivative.
  • UsesSignificantly accelerated the polymerization of pheneylacetylene in conjunction with rhodium (I) catalysis
  • Purification MethodsIt can be sublimed at 170o/2mm (bath temperature 220-250o) onto a cold finger, and can be recrystallised from *C6H6 (its solubility is: 10g in 100mL at 60o). It is slightly soluble in Et2O and is decomposed by H2O. [Wannagat & Niederprüm Chem Ber 94 1540 1961.]It is available commercially under N2 in Sure/Seal bottles in tetrahydrofuran (various concentrations) and at ~0.6M in toluene. [Beilstein 4 IV 4014.]
Sodium bis(trimethylsilyl)amide Preparation Products And Raw materials
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