Sodium Triacetoxyborohydride, is a mild borohydride reducing agent. Its CAS Number is 56553-60-7, widely used reducing agent in modern organic chemistry and pharmaceutical synthesis.

 

Technical Specifications

ITEMS SPECIFICATIONS
Appearance White powder
Assay ≥97%

 

Package & Storage

  • Net weight 25kgs drum.
  • Store a cool dry place, keep away from light. Best used within 6 months after opening the bag.

 

Key Benefits of Sodium Triacetoxyborohydride

High Selectivity in Reductive Amination:
Reduces imines/iminium ions preferentially over aldehydes and ketones, enabling efficient one-pot direct reductive amination without significant carbonyl reduction.

Mild Reaction Conditions:
Operates at room temperature or mildly acidic conditions, minimizing side reactions and protecting sensitive functional groups.

Safer Alternative to Sodium Cyanoborohydride:
Avoids toxic cyanide byproducts, improving worker safety and simplifying waste disposal.

Broad Substrate Scope:
Effective for aldehydes, ketones, and amines (primary and secondary), widely used in amine synthesis for drug candidates.

 

Primary Applications and Uses of Sodium Triacetoxyborohydride

Sodium Triacetoxyborohydride is predominantly used in organic synthesis and pharmaceutical intermediate production:

Reductive Amination (Primary Use)

  • One-pot conversion of aldehydes/ketones + amines → secondary/tertiary amines.
  • Ideal for direct reductive amination where carbonyl and imine coexist.
  • Preferred solvent: DCE or DCM; additives like acetic acid enhance rate and selectivity.

Other Organic Transformations

  • Selective reduction of aldehydes in the presence of ketones.
  • Reduction of enamines and imines in complex molecules.
  • Synthesis of β-amino acids, heterocycles, and chiral amines.

Pharmaceutical and Research Industry

  • Key step in API synthesis requiring amine installation.
  • Used in medicinal chemistry libraries and lead optimization.
  • Scalable for process chemistry due to mildness and selectivity.

 

Frequently Asked Questions (FAQs)

Q: Why is STAB preferred over sodium cyanoborohydride for reductive amination?
A: STAB offers comparable or better selectivity without producing toxic cyanide byproducts, improving safety and environmental profile.

Q: What solvents are best for reactions with Sodium Triacetoxyborohydride?
A: Aprotic solvents like 1,2-dichloroethane (DCE), dichloromethane (DCM), THF, dioxane, or toluene are recommended. Avoid water and protic solvents like methanol (fast decomposition); ethanol/IPA react slowly.

Q: Can STAB reduce aldehydes selectively in the presence of ketones?
A: Yes, STAB reduces aldehydes significantly faster than ketones under standard conditions, making it useful for chemoselective reductions.

Q: How should Sodium Triacetoxyborohydride be stored?
A: Store under inert atmosphere in a cool, dry place in tightly sealed containers to prevent moisture absorption and decomposition.

Q: Is Sodium Triacetoxyborohydride suitable for large-scale pharmaceutical synthesis?
A: Yes, its mild nature, high selectivity, and favorable safety profile make it widely used in process-scale reductive aminations for drug intermediates.

 

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