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Sodium triacetoxyborohydride

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Sodium triacetoxyborohydride Basic information
Sodium triacetoxyborohydride Chemical Properties
  • Melting point:116-120 °C (dec.)(lit.)
  • storage temp. Flammables + water-Freezer (-20°C)e area
  • solubility Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride.
  • form Powder
  • color White
  • Water Solubility reacts
  • Sensitive Moisture Sensitive
  • Merck 14,8695
  • BRN 4047608
  • InChIKeyHHYFEYBWNZJVFQ-UHFFFAOYSA-N
  • CAS DataBase Reference56553-60-7(CAS DataBase Reference)
  • EPA Substance Registry SystemBorate(1-), tris(acetato-.kappa.O)hydro-, sodium, (T-4)- (56553-60-7)
Safety Information
MSDS
  • Language:EnglishProvider:STAB
  • Language:EnglishProvider:ACROS
  • Language:EnglishProvider:SigmaAldrich
  • Language:EnglishProvider:ALFA
Sodium triacetoxyborohydride Usage And Synthesis
  • Chemical Propertieswhite powder
  • Uses
    1. Sodium Triacetoxyborohydride(STAB) is a hydride reagent used in stereoselective reductive amination. It is able to replace toxic sodium cyanoborohydride under most conditions. It is selective in reducing aldehydes to alcohols in the presence of ketones. STAB is also stable in anhydrous acids, which enables reductive amination of aldehydes and ketones. It  used in reductive amination of ketones and aldehydes and reductive amination/lactamization of carbonyl compounds with amines.
    2. Reagent for the reductive amination of aryl aldehydes.The advantage of STAB compared to sodium cyanoborohydride is evident. STAB, being non-toxic, is easier to handle and forms no toxic by-products, making the treatment of process waste after the reaction simple and less costly.
    3. Selective reducing agent in organic synthesis.
    4. Sodium triacetoxyborohydride is especially suitable for reductive aminations. Since the reaction rate for the reduction of iminium ions is much faster than for ketones or even aldehydes, the reductive amination can be carried out as a one-pot procedure by introducing the reducing agent into a mixture of the amine and carbonyl compound. The presence of a stoichiometric amount of acetic acid, which catalyzes the imine formation and provides the iminium ion, doesn't present any problem under these conditions.
      Reductive amination (simplified)
      Reductive amination (simplified)
Sodium triacetoxyborohydride Preparation Products And Raw materials
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