Home > Compound List > Product Information
Sodium borohydride_Molecular_structure_CAS_16940-66-2)
Click picture or here to close

Sodium borohydride

Catalog No. 13432 Name Alfa Aesar
CAS Number 16940-66-2 Website
M. F. BNa Telephone
M. W. 33.80077 Fax
Purity 98% Email
Storage Chembase ID: 102741

SYNONYMS

Title
硼氢化钠
IUPAC name
sodium boranuide
IUPAC Traditional name
sodium boranuide
Synonyms
Sodium tetrahydridoborate

DATABASE IDS

MDL Number MFCD00003518
Merck Index 148592
EC Number 241-004-4
CAS Number 16940-66-2

PROPERTIES

Purity 98%
Apperance Powder
Density 1.074
Melting Point 400°C dec.
GHS Pictograms GHS02
GHS Pictograms GHS05
GHS Pictograms GHS06
GHS Hazard statements H301-H311-H331-H314-H318-H261
European Hazard Symbols Toxic Toxic (T)
European Hazard Symbols Flammable Flammable (F)
GHS Precautionary statements P280-P303+P361+P353-P305+P351+P338-P310-P370+P378I-P402+P404
Risk Statements 15-23/24/25-34
RTECS ED3325000
Safety Statements 7/8-26-36/37/39-43-45
Storage Warning Moisture Sensitive
TSCA Listed
Hazard Class 4.3
UN Number UN1426
Packing Group I

DETAILS

REFERENCES

  • The reduction of aldehydes and ketones to alcohols occurs in alcoholic or aqueous media. For highly selective reduction of aldehydes in the presence of ketones, see: Synth. Commun., 18, 1927 (1988). For enantioselective reduction, see L-tert-Leucine, L13707. Borohydride reductions can be carried out in organic solvents, e.g. toluene, under phase-transfer conditions, amenable to scale-up: Org. Process Res. Dev., 1, 287 (1997).
  • Hydroboration of olefins has also been reported under similar conditions: Synlett, 997 (2000).
  • Acid chlorides are readily reduced to alcohols; controlled reduction at -78o to give the aldehyde has been reported; see, e.g.: Synth. Commun., 12, 839 (1982). See also Bis(triphenylphosphine)copper(I) borohydride, A13730. For an indirect method of reduction, see Triethyl phosphite, L00339.
  • A vast number of modified borohydride reagents have been reported, with the objective either of increasing the reducing power or improving selectivity. Many examples involve combinations with metal salts:
  • Reductive alkylation of amines can be effected with NaBH4/formaldehyde; see e.g.: Synthesis, 743 (1980); or TFA: Synthesis, 709 (1987). See also Sodium cyanoborohydride, 87839. Reductive alkylation of aromatic amines with a variety of aldehydes and ketones has been reported, using NaBH4/H2SO4: Synthesis, 121 (1993).
  • For a brief feature on uses of the reagent in synthesis, see: Synlett, 182 (2005).
  • Monograph: J. Seyden-Penne, Reductions by the Alumino- and Borohydrides In Organic Synthesis, 2nd ed., Wiley, N.Y. (1997).
  • LiCl: reduction of amino acids via Me esters: Tetrahedron Lett., 39, 917 (1998). CaCl2: selective 1,2-reduction enones: Chem. Lett., 1847 (1991). CeCl3: increased selectivity for 1,2-reduction of enones: J. Chem. Soc., Chem. Commun., 601 (1978); reduction of ketones in the presence of aldehydes: J. Am. Chem. Soc., 101, 5848 (1979). CuCl: dehalogenation of aryl iodides and bromides: J. Org. Chem., 54, 5308 (1989); reduction of nitro compounds: Chem. Ind. (London), 75 (1984). CuSO4: reduction of esters, alkenes, nitriles and nitro compounds; amides and acids inert: Synlett, 419 (1990) [but see also Synlett, 79 (1993): Cu(OAc)2 preferred for reduction of nitro-groups]; reduction of azides: Synth. Commun., 24, 549 (1994). NiCl2: generation in situ of nickel boride, as an alternative to Raney nickel for desulfurizations: Synth. Commun., 16, 779 (1986); J. Chem. Soc., Chem. Commun., 819 (1990); J. Org. Chem., 57, 1986 (1992); 58, 2407 (1993); phenols and enols have also been deoxygenated: J. Chem. Soc., Perkin 1, 1897 (1992), and aryl nitrile reduced to benzylamines: Synth. Commun, 32, 1265 (2002). For conversion to Zn(BH4)2, see Zinc chloride, A16281. InCl3: radical reducing system - alternative to Bu3SnH: J. Am. Chem. Soc., 124, 906 (2002) .
  • The combination of borohydride and iodine (in situ borane) reduces acids to alcohols: J. Org. Chem., 56, 5964 (1991); amino acids to amino alcohols: J. Org. Chem., 58, 3568 (1993); and effects reduction of esters, amides and nitriles, as well as hydroboration of alkenes: Tetrahedron, 45, 4623 (1992). See also Boron trifluoride diethyl etherate, A15275, and Sodium triacetoxyborohydride, B22060.