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25895-60-7 molecular structure
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sodium cyanoboranuide

ChemBase ID: 88866
Molecular Formular: CH2BNNa
Molecular Mass: 61.83405
Monoisotopic Mass: 62.01779875
SMILES and InChIs

SMILES:
[BH2-]C#N.[Na+]
Canonical SMILES:
[BH2-]C#N.[Na+]
InChI:
InChI=1S/CH3BN.Na/c2-1-3;/h2H3;/q-1;+1
InChIKey:
CVDUGUOQTVTBJH-UHFFFAOYSA-N

Cite this record

CBID:88866 http://www.chembase.cn/molecule-88866.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
sodium cyanoboranuide
IUPAC Traditional name
sodium cyanoboranuide
Synonyms
Sodium cyanoborohydride
Sodium cyanotrihydroborate
Sodium cyanoborohydride
Sodium borocyanohydride
Sodium cyanotrihydroborate
Sodium cyanoborohydride solution
Sodium cyanotrihydridoborate
SODIUM CYANOBOROHYDRIDE
Sodium (T-4)-(Cyano-C)trihydroborate(1-)
Sodium Cyanotrihydroborate(1-)
氰基硼氢化钠
氰基硼氢化钠
氰基硼氢化钠 溶液
CAS Number
25895-60-7
EC Number
247-317-2
MDL Number
MFCD00003516
Beilstein Number
4152656
Merck Index
148606
PubChem SID
24849595
162075764
24857889
24857879
PubChem CID
20587905
Wikipedia Title
Sodium_cyanoborohydride

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -1.5879  LogD (pH = 7.4) -1.5879 
Log P -1.5879  Molar Refractivity 9.0556 cm3
Polarizability 4.7723866 Å3 Polar Surface Area 23.79 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO (Sparingly) expand Show data source
H2O: soluble, clear to slightly hazy expand Show data source
Methanol expand Show data source
soluble in water expand Show data source
Soluble in water, THF, methanol expand Show data source
Apperance
Powder expand Show data source
White Solid expand Show data source
white to off-white powder, hygroscopic expand Show data source
Melting Point
>242 °C (dec.)(lit.) expand Show data source
>242°C expand Show data source
>242(dec.)°C expand Show data source
>300°C expand Show data source
>300°C dec. expand Show data source
241 °C decomp. expand Show data source
Flash Point
1.4 °F expand Show data source
-17 °C expand Show data source
Density
0.915 g/mL at 25 °C expand Show data source
1.083 g/mL at 25 °C expand Show data source
1.20 expand Show data source
1.20 g/cm3 expand Show data source
Storage Condition
Refrigerator, Under Inert Atmosphere expand Show data source
Room Temperature (15-30°C), Desiccate, Store Under Nitrogen expand Show data source
Storage Warning
Highly Flammable/Very Toxic/Corrosive/Moisture Sensitive/Store under Argon expand Show data source
Moisture Sensitive expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Nature polluting Nature polluting (N) expand Show data source
Toxic Toxic (T) expand Show data source
Highly toxic Highly toxic (T+) expand Show data source
UN Number
1992 expand Show data source
2922 expand Show data source
3179 expand Show data source
UN3134 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
3 expand Show data source
4.1 expand Show data source
4.3 expand Show data source
6.1 expand Show data source
8 expand Show data source
Packing Group
2 expand Show data source
II expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
11-15-26/27/28-32-34-50/53 expand Show data source
11-19-23/24/25-32-36/37/38-50/53 expand Show data source
26/27/28-32-34-50/53 expand Show data source
R:10-25 expand Show data source
Safety Statements
16-26-36/37-45-61 expand Show data source
26-28-36/37/39-43-45-61 expand Show data source
26-28-36/37/39-45-60-61 expand Show data source
26-28-36/37/39-45-61 expand Show data source
S:16-28-29-36/37/39-45 expand Show data source
EU Classification
FT2 expand Show data source
EU Hazard Identification Number
4.1B expand Show data source
Emergency Response Guidebook(ERG) Number
134 expand Show data source
TSCA Listed
expand Show data source
EU Index
not listed expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS05 expand Show data source
GHS06 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Danger expand Show data source
NFPA704
NFPA 704 diagram
2
3
2
W
expand Show data source
GHS Hazard statements
H225-H301-H311-H314-H330-H335-H400-H411 expand Show data source
H228-H260-H300-H310-H314-H330-H410 expand Show data source
H228-H261-H300-H310-H330-H314-H318-H400-H410 expand Show data source
H300-H310-H314-H330-H410 expand Show data source
GHS Precautionary statements
P210-P223-P231 + P232-P260-P370 + P378-P422 expand Show data source
P210-P260-P273-P280-P284-P301 + P310 expand Show data source
P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A expand Show data source
P260-P264-P273-P280-P284-P301 + P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 1992 3/PG 2 expand Show data source
UN 2922 8/PG 2 expand Show data source
UN 3179 4.1/PG 2 expand Show data source
Supplemental Hazard Statements
Contact with acids liberates very toxic gas. expand Show data source
Contact with acids liberates very toxic gas., May form explosive peroxides. expand Show data source
Purity
≥95% expand Show data source
≥95.0% (RT) expand Show data source
90% expand Show data source
95% expand Show data source
Concentration
1.0 M in THF expand Show data source
5.0 M in 1 M NaOH expand Show data source
Grade
purum expand Show data source
reagent grade expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Linear Formula
NaBH3CN expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02199862 external link
Aqueous solutions may be slightly hazy.
MP Biomedicals - 02156628 external link
Purity: 90% Aqueous solutions may be slightly hazy.
Sigma Aldrich - 296945 external link
Packaging
50, 500 mL in poly bottle
Application
Reactant for:
• Direct conversion of heterocyclic aldehydes to esters (oxidizing behavior)1
• Reductive amination reactions2
• Intramolecular reductive cyclization reactions3
• Reductions reactions4
• Preparation of dicyanoborate-based ionic liquids as hypergolic fluids for bipropellants5
Sigma Aldrich - 296813 external link
Packaging
100, 800 mL in Sure/Seal™
Application
Reactant for:
• Direct conversion of heterocyclic aldehydes to esters (oxidizing behavior)1
• Reductive amination reactions2
• Intramolecular reductive cyclization reactions3
• Reductions reactions4
• Preparation of dicyanoborate-based ionic liquids as hypergolic fluids for bipropellants5
Sigma Aldrich - 156159 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Reagent employed in the reductive amination of aldehydes1 and ketones,2 and in the reductive alkylation of amines.3
Reagent for selective reductions.
Features and Benefits
Used in the synthesis of a novel phenolate-bridged dilanthanum(III) complex of interest as a model for metalloproteins as well as for its importance in basic and applied chemistry.4
Packaging
1 kg in poly bottle
10 kg in steel drum
10, 25, 50, 250 g in poly bottle
Sigma Aldrich - 71435 external link
Other Notes
Review1,2; selctive reductions with NaCNBH3, modified with zinc chloride3; with zinc iodide4
Toronto Research Chemicals - S615500 external link
Sodium Cyanoborohydride is a commonly used as a reagent in the reductive amination of aldehydes and ketones and in the reductive alkylation of amines.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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