Sodium cyanoborohydride

• Catalog No.: 87839
• CAS Number: 25895-60-7
• M. F.: CH2BNNa
• M. W.: 61.83405
• Purity: 95%

SYNONYMS

• Title: 氰基硼氢化钠
• IUPAC name: sodium cyanoboranuide
• IUPAC Traditional name: sodium cyanoboranuide
• Synonyms: Sodium cyanotrihydridoborate

DATABASE IDS

• Merck Index: 148606
• EC Number: 247-317-2
• MDL Number: MFCD00003516
• CAS Number: 25895-60-7

PROPERTIES

• Purity: 95%
• Apperance: Powder
• Density: 1.20
• Melting Point: >300°C dec.
• Solubility: Soluble in water, THF, methanol
• GHS Hazard statements: H228-H261-H300-H310-H330-H314-H318-H400-H410
• European Hazard Symbols: Highly toxic (T+)
• European Hazard Symbols: Flammable (F)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A
• Risk Statements: 11-15-26/27/28-32-34-50/53
• Safety Statements: 26-28-36/37/39-45-60-61
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 4.3
• UN Number: UN3134
• Packing Group: II

REFERENCES

• Unlike borohydride reduction of carbonyl compounds which proceeds readily at the natural pH of the solution, reduction by sodium cyanoborohydride is very slow unless the pH is reduced to 3-4. Selective reduction of iminium ions occurs, however, at pH 6-8, leading to the widespread application of the reagent in reductive aminations of carbonyl compounds: J. Am. Chem. Soc., 93, 2897 (1971); Org. Synth. Coll., 6, 499 (1988). For improved methods using combinations with Ti(IV) chloride or isopropoxide, see: Tetrahedron Lett., 31, 5547 (1990); J. Org. Chem., 55, 2552 (1990).
• Monograph: J. Seyden-Penne, Reductions by the Alumino- and Borohydrides In Organic Synthesis, 2nd ed., Wiley, N.Y. (1997).
• Tosylhydrazones are reduced to methylenes. The relatively slow reduction of carbonyl compounds enables the tosylhydrazone to be generated in situ: J. Am. Chem. Soc., 93, 1793 (1971); 95, 3662 (1973). For a detailed study of the mechanism of tosylhydrazone reduction, see: J. Org. Chem., 54, 4175 (1989).
• Oximes are reduced to hydroxylamines, as are O-alkyloximes: Tetrahedron Lett., 2493 (1974). Reduction in the presence of TiCl₃ gives primary amines, via the imine: Synth. Commun., 18, 777 (1988).
• For reviews of the chemistry of sodium cyanoborohydride, see: Synthesis, 135 (1975); Org. Prep. Proced. Int., 11, 201 (1979).