Sodium cyanoborohydride
| Sodium cyanoborohydride | |
| Names | |
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| Other names
Sodium cyanotrihydridoborate
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| Identifiers | |
25895-60-7  |
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| EC Number | 247-317-2 |
| Jmol 3D model | Interactive image |
| PubChem | 20587905 |
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| Properties | |
| NaBH3CN | |
| Molar mass | 62.84 gmol−1 |
| Appearance | white to off-white powder, hygroscopic |
| Density | 1.20 g/cm3 |
| Melting point | 241 °C (466 °F; 514 K) decomposes |
| 212 g/100 mL (29 °C) | |
| Solubility | soluble in diglyme, tetrahydrofuran, methanol slightly soluble in methanol insoluble in diethyl ether |
| Vapor pressure | {{{value}}} |
| Related compounds | |
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Other anions
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Sodium borohydride |
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Related compounds
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Lithium aluminium hydride |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Sodium cyanoborohydride is the chemical compound with the formula NaBH3CN. It is a colourless salt, but commercial samples can appear tan. It is widely used in organic synthesis for the reduction of imines. The salt tolerates aqueous conditions.[1]
Use
Owing to the presence of the electron-withdrawing cyanide substituent, [B(CN)H3]− is far less reducing than is [BH4]−, as found in sodium borohydride.[2] As a mild reducing agent, it is especially used to convert imines to amines.
It is especially favored for reductive aminations, wherein aldehydes or ketones are treated with an amine in the presence of this reagent:
- R2CO + R'NH2 + NaBH3CN + CH3OH → R2CH-NHR' + "NaCH3OBH2CN"
The reagent is typically used in excess. Selectivity is achieved at mildly basic solutions (pH 7-10). The reagent is ideal for reductive aminations ("Borch Reaction").[3] In conjunction with tosylhydrazine, sodium cyanoborohydride is used in the reductive deoxygenation of ketones.[1]
Structure and preparation
The tetrahedral anion BH3(CN)− comprises the salt.
The reagent is invariably purchased, although it can be prepared easily. One method involves combining sodium cyanide and borane. Another route entails treating sodium borohydride with mercury(II) cyanide. The commercial samples can be purified but the yields of the reductive aminations do not improve.[4]
See also
- Sodium triacetoxyborohydride - a milder reductant and a less toxic alternative, but highly unstable in water
References
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This inorganic compound–related article is a stub. You can help Wikipedia by expanding it. |
- ↑ 1.0 1.1 Robert O. Hutchins, MaryGail K. Hutchins, Matthew L. Crawley "Sodium Cyanoborohydride" Encyclopedia of Reagents for Organic Synthesis, 2007 John Wiley & Sons. doi:10.1002/047084289X.rs059.pub2
- ↑ Ellen W. Baxter, Allen B. Reitz Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents in Organic Reactions, 2002, John Wiley and Sons. doi:10.1002/0471264180.or059.01
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