Sodium cyanoborohydride

It is a colourless salt used in organic synthesis for chemical reduction including that of imines and carbonyls.

The electron-withdrawing cyanide substituent draws electron density away from the negatively charged boron; thus, reducing the electrophilic capabilities of the anionic component.

[7] Since sodium cyanoborohydride is a mild reducing agent, it gives good chemoselectivity for reaction with certain functional groups in the presence of others.

For example, sodium cyanoborohydride is generally incapable of reducing amides, ethers, esters and lactones, nitriles, or epoxides.

Georg Wittig was the first to synthesize a cyanoborohydride by treating lithium borohydride with hydrogen cyanide in 1951.

[10] The synthesis was later refined to use sodium cyanide and borane in THF making the process safer.

Line-bond structure of sodium cyanoborohydride
Line-bond structure of sodium cyanoborohydride
NFPA 704 four-colored diamond Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus Special hazards (white): no code