Sodium cyanoborohydride

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Sodium cyanoborohydride
Sodium cyanoborohydride
Other names Sodium cyanotrihydridoborate
Identifiers
CAS number [25895-60-7]
Properties
Molecular formula NaBH3CN
Molar mass 62.84 g/mol
Appearance white to off-white powder
hygroscopic
Density 1.20 g/cm³, solid
Melting point

241°C (decomposes)

Solubility in water soluble
Hazards
EU classification not listed
NFPA 704
3
4
2
 
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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.[1]

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.

[edit] 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.[2] Even though the molecule is water sensitive it can be used to perform reactions in an aqueous environment.[3]

[edit] References

  1. ^ Safety (MSDS) data for sodium cyanoborohydride
  2. ^ Richard F. Borch and Mark D. Bernstein and H. Dupont Durst, Cyanohydridoborate Anion as a Selective Reducing Agent, J Am Chem Soc, 2897-2904, 93(12),1971
  3. ^ Timothy M. Beard and Nicholas J. Turner, Deracemisation and Stereoinversion of alpha-Amino Acids Using D-Amino Acid Oxidase and Hydride Reducing Agents, Chemical Communications, 246-247, 2002