Sodium cyanoborohydride

Sodium cyanoborohydride (NaBH₃(CN)) is a chemical compound.

Conditions/substances to avoid are: heat, flame, ignition sources, water, moist air, strong acids and strong oxidizers.

Strong acids on sodium cyanoborohydride release cyanide. The slow decomposition of sodium cyanoborohydride by water in the atmosphere also causes the release of cyanide and care must be taken when opening containers, as the gas can build up within.

Uses

Sodium cyanoborohydride is a mild reducing agent, ideal for reducing imines selectively in the presence of aldehydes or ketones. This makes it excellent for performing reductive aminations and this reaction is known as the Borch Reaction. Even though the molecule is water sensitive it can be used to perform reactions in an aqueous environment.

In addition, sodium cyanoborohydride is often used in hydrogenolysis reactions, such as the opening of acetals.

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