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Sodium triacetoxyborohydride (STAB) is a versatile reducing agent widely used in organic synthesis for the selective reduction of various functional groups. Here's a detailed overview of its properties, synthesis, and applications: 1. Chemical Structure and Properties: Sodium triacetoxyborohydride has the chemical formula NaBH(OAc)₃, where OAc represents the acetate group (-OOCCH₃). It is a white to off-white crystalline powder that is soluble in polar solvents such as water, alcohols, and acetone. The reagent is moisture-sensitive and should be stored in a dry environment to prevent decomposition. 2. Synthesis: Sodium triacetoxyborohydride is typically prepared by the reaction of sodium borohydride (NaBH₄) with acetic anhydride (Ac₂O) in the presence of a boron trifluoride catalyst. The reaction proceeds through the formation of an intermediate boronate complex, which undergoes further acetylation to yield sodium triacetoxyborohydride. 3. Reducing Properties: STAB is a mild and selective reducing agent commonly used for the reduction of various functional groups, including ketones, aldehydes, imines, and epoxides. It exhibits higher chemoselectivity compared to other common reducing agents such as lithium aluminum hydride (LiAlH₄) and sodium borohydride (NaBH₄), making it particularly useful for complex molecule synthesis.

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