Sodium cyanoborohydride
5063927
225115882
2008-07-11T23:18:59Z
72.93.68.89
{{Chembox new
| Name = Sodium cyanoborohydride
| ImageFile = Sodium-cyanoborohydride-2D.png
<!-- | ImageSize = 200px -->
| ImageName = Sodium cyanoborohydride
| OtherNames = Sodium cyanotrihydridoborate
| Section1 = {{Chembox Identifiers
| CASNo = 25895-60-7
}}
| Section2 = {{Chembox Properties
| Formula = NaBH<sub>3</sub>CN
| MolarMass = 62.84 g/mol
| Appearance = white to off-white powder<br />[[hygroscopic]]
| Density = 1.20 g/cm³, solid
| Solubility = soluble
| MeltingPt = 241°C (decomposes)
| BoilingPt =
}}
| Section7 = {{Chembox Hazards
| EUClass = not listed
| NFPA-H = 4
| NFPA-R = 2
| NFPA-F = 3
| NFPA-O = W
}}
}}
'''Sodium cyanoborohydride''' ([[Sodium|Na]][[Boron|B]][[Hydrogen|H<sub>3</sub>]]([[Carbon|C]][[Nitrogen|N]])) is a [[chemical compound]].
Conditions/substances to avoid are: heat, [[flame]], [[ignition]] sources, water, [[moist]] air, strong [[acid]]s and strong [[oxidizer]]s.<ref>[http://msds.chem.ox.ac.uk/SO/sodium_cyanoborohydride.html Safety (MSDS) data for sodium cyanoborohydride<!-- Bot generated title -->]</ref>
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 amination]]s and this reaction is known as the [[Borch Reaction]].<ref>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</ref> Even though the molecule is water sensitive it can be used to perform reactions in an aqueous environment.<ref>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</ref>
==References==
{{Unreferenced|date =September 2007}}
{{reflist}}
[[Category:Boron compounds]]
[[Category:Sodium compounds]]
{{inorganic-compound-stub}}
[[ar:سيان بورهيدريد صوديوم]]
[[de:Natriumcyanoborhydrid]]
[[es:Cianoborohidruro de sodio]]
[[fr:Cyanoborohydrure de sodium]]
[[zh:氰基硼氢化钠]]