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]]