Chemical Name: Sodium Triacetoxyborohydride
Molecular Formula: C6H10BNaO6
CAS Number: 56553-60-7
Molecular Weight: 211.94 g/mol
IUPAC Name: Sodium triacetoxyborohydride
Appearance: White to off-white crystalline powder
Solubility: Soluble in acetonitrile, dichloromethane, THF; decomposes in water
Melting Point: ~120-122°C (with decomposition)

Description

Sodium Triacetoxyborohydride (STAB) is a highly selective reducing agent widely used in organic synthesis, particularly in reductive amination reactions. It is an acyloxy borohydride that offers superior selectivity compared to sodium cyanoborohydride, especially in the reductive amination of aldehydes and ketones with primary or secondary amines. Its mild reaction conditions make it a reagent of choice for sensitive substrates that require careful control during reduction processes.

Sodium Triacetoxyborohydride is often preferred in synthetic chemistry due to its lower toxicity compared to cyanoborohydride and its ease of handling under non-aqueous conditions. The reagent is stable in alcohols and aprotic solvents, and it does not require the presence of a proton source for effective reduction. It is especially useful for reducing imines and iminium ions, which are intermediate species in reductive amination reactions.