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Sodium cyanoborohydride

Catalog No. 87839 Name Alfa Aesar
CAS Number 25895-60-7 Website
M. F. CH2BNNa Telephone
M. W. 61.83405 Fax
Purity 95% Email
Storage Chembase ID: 88866

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 Pictograms GHS02
GHS Pictograms GHS05
GHS Pictograms GHS06
GHS Pictograms GHS09
GHS Hazard statements H228-H261-H300-H310-H330-H314-H318-H400-H410
European Hazard Symbols Highly toxic Highly toxic (T+)
European Hazard Symbols Flammable Flammable (F)
European Hazard Symbols Nature polluting 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
Hazard Class 4.3
UN Number UN3134
Packing Group II

DETAILS

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).