What is Sodium cyanoborohydride CAS 25895-60-7

Sodium cyanoborohydride, also known as sodium cyanide borohydride or NaBH3CN, is a compound with the chemical formula NaBH3CN. It is an effective and mild reducing agent, especially suitable for reducing carbonyl compounds such as aldehydes and ketones to their corresponding alcohols.

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Synonyms

SodiuM cyanohydridoborate; Sodium cyanoborohydride, 1M solution in THF, AcroSeal; (cyano-C)trihydro-,sodium,(T-4)-Borate(1-); SodiuM (T-4)-(Cyano-C)trihydroborate(1-); sodium,(beta-4)-borate(1-(cyano-c)trihydro-; Sodium cyanoborohydride,Sodium cyanotrihydridoborate; Sodium Cyanotrihydridoborate; Sodium cyanotrihydroborate(1-); Borate(1-), (cyano-κC)trihydro-, sodium, (T-4)-; Sodium cyanotrihydroborate; Sodium borocyanohydride; Sodium cyanoboranuide; Borate(1-), cyanotrihydro-, sodium; Borate(1-), (cyano-κC)trihydro-, sodium (1:1), (T-4)-; Borate(1-), (cyano-C)trihydro-, sodium, (T-4)-; Sodium cyanoboronhydride; Sodium cyanoborohydride, 1M solution in THF, AcroSeal§3;

sodium cyanoborohydride reductive amination mechanism

The reductive amination mechanism involving sodium cyanoborohydride consists of several steps, which can be described as follows:

First, an amine and a carbonyl compound (aldehyde or ketone) undergo a reaction in the presence of an acid catalyst. This results in the formation of an intermediate called an imine. The amine acts as a nucleophile, attacking the carbonyl carbon, while the acid catalyst facilitates the reaction.

Next, sodium cyanoborohydride, acting as a hydride donor, is introduced into the reaction mixture. The hydride ion (H-) from sodium cyanoborohydride attacks the imine carbon, leading to the formation of a secondary amine.

The resulting secondary amine is commonly obtained as a hydrochloride salt, which can be further processed to obtain the free amine. This can be achieved by treating the salt with a base or by adding acid followed by extraction.

In summary, sodium cyanoborohydride serves as a mild and selective reducing agent that facilitates the conversion of carbonyl compounds to amines in a reductive amination process. This mechanism involves the formation of an imine intermediate followed by its reduction with hydride ions from sodium cyanoborohydride, resulting in the formation of a secondary amine.

nabh3cn reaction

When sodium cyanoborohydride (NaBH3CN) participates in a reaction, it follows a specific process. Firstly, an amine and a carbonyl compound (aldehyde or ketone) undergo a reaction in the presence of an acid catalyst. This results in the formation of an intermediate called an imine. The amine, acting as a nucleophile, attacks the carbonyl carbon, while the acid catalyst aids in this reaction.

Next, sodium cyanoborohydride, which acts as a hydride donor, is added to the reaction mixture. The hydride ion (H-) from NaBH3CN then reacts with the imine carbon, leading to the formation of a secondary amine.

The resulting secondary amine is typically obtained as a hydrochloride salt, and further processing is required to obtain the free amine. This can be achieved by treating the salt with a base or by adding acid followed by extraction.

In summary, sodium cyanoborohydride, through a series of steps, enables the conversion of carbonyl compounds to amines in a reaction known as reductive amination. This involves the formation of an imine intermediate followed by its reduction using hydride ions from NaBH3CN, resulting in the production of a secondary amine.