Sodium cyanoborohydride
CAS 25895-60-7
MF: CH3BNNa
hydride is a milder and more selective reducing agent than sodium borohydride.
Sodium cyanoborohydride is a weaker and more-selective reducing agent than sodium borohydride because of the electron-withdrawing effect of the cyano group. It has the further advantage that it is stable in acid to pH = 3 and can be employed to effect reductions in the presence of functional groups that are sensitive to the more-basic conditions of reduction with sodium borohydride.
Description
Sodium cyanoborohydride CAS 25895-60-7 Product Information
| Product Name: | Sodium cyanoborohydride |
| Synonyms: | Sodium cyanoborohydride;sodium cyanohydroboride;Sodium cyanohydridoborate;MFCD00003516;sodium cyanoborohydride solution;EINECS 247-317-2;Sodium cyonobrohydriole;Sodium (cyano-κC)(trihydrido)borate(1-);SODIUM CYANOTRIHYDROBORATE;Borate(1-), (cyano-κC)trihydro-, sodium (1:1);sodium cyano borohydride;sodium borocyanohydride;SODIUM CYANOTRIHYDRIDOBORATE |
| CAS NO: | 25895-60-7 |
| Molecular Weight: | 62.84 |
| Molecular Formula: | CH3BNNa |
| Boiling Point: | 307°C |
| Melting point: | >242 °C (dec.) (lit.) |
| Density: | 1.083 g/mL at 25 °C |
| Appearance: | White powder |
| Purity: | >98% |
| Stability: | Avoid contact with oxides, acids, moisture/humidity |
| Storage: | Store under dry nitrogen or argon atmosphere. |
sodium cyanoborohydride cas/sodium cyanoborohydride cas no
25895-60-7
sodium cyanoborohydride preparation
Synthesis of Sodium cyanoborohydride(NaBH3CN): NaBH3CN was made by stirring equimolar BH3·THF (~1 M) with NaCN in THF in excellent yield.To a rapidly stirred slurry of sodium borohydride (80.2g, 2.09 mol) in THF (1000mL) in a 2-L flask is added a solution of hydrogen cyanide in THF (294g containing 58.8g of hydrogen cyanide) at 25°C. Evolution of hydrogen occurs slowly during the addition. Following the addition, the reaction mixture is stirred for 1 h at 25°C and then heated at reflux until hydrogen evolution has ceased. Filtration followed by vacuum removal of THF gives white solid sodium cyanoborohydride; yield 120g (91%).
sodium cyanoborohydride mechanism/sodium cyanoborohydride reduction
Tin-free Giese reaction of alkyl iodides with electron-deficient alkenes and the related radical carbonylation process proceeded efficiently in the presence of sodium cyanoborohydride and tetrabutylammonium cyanoborohydride. Transfer of iodine followed by hydride reduction of the resulting carbon-iodine bond is proposed as a possible mechanism.
sodium cyanoborohydride quenching
The following views come from reddit:You can quench cyanide with bleach.
sodium cyanoborohydride reductive amination
Sodium cyanoborohydride (NaBH3CN) is a mild reducing agent that is commonly used in reductive aminations. The presence of the electron-withdrawing cyano (CN) group makes it less reactive than sodium borohydride (NaBH4).
sodium cyanoborohydride vs sodium borohydride
Sodium cyanoborohydride (NaBH3CN) is a mild reducing agent that is commonly used in reductive aminations. The presence of the electron-withdrawing cyano (CN) group makes it less reactive than sodium borohydride (NaBH4).
sodium cyanoborohydride safety
Precautionary statement(s) P260 Do not breathe dust/ fume/ gas/ mist/ vapors/ spray. P280 Wear protective gloves/ protective clothing/ eye protection/ face protection. P303 + P361 + P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water.
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