sodium cyanoboranuide

• ChemBase ID: 88866
• Molecular Formular: CH2BNNa
• Molecular Mass: 61.83405
• Monoisotopic Mass: 62.01779875
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 25895-60-7
• EC Number: 247-317-2
• MDL Number: MFCD00003516
• Beilstein Number: 4152656
• Merck Index: 148606
• PubChem SID: 24849595; 24857889; 162075764; 24857879
• PubChem CID: 20587905
• Wikipedia Title: Sodium_cyanoborohydride

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -1.5879
• LogD (pH = 7.4): -1.5879
• Log P: -1.5879
• Molar Refractivity: 9.0556 cm^3
• Polarizability: 4.7723866 Å^3
• Polar Surface Area: 23.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO (Sparingly); H2O: soluble, clear to slightly hazy; Methanol; soluble in water; Soluble in water, THF, methanol
• Apperance: Powder; White Solid; white to off-white powder, hygroscopic
• Melting Point: >242 °C (dec.)(lit.); >242°C; >242(dec.)°C; >300°C; >300°C dec.; 241 °C decomp.
• Flash Point: 1.4 °F; -17 °C
• Density: 0.915 g/mL at 25 °C; 1.083 g/mL at 25 °C; 1.20; 1.20 g/cm^3

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• Storage Warning: Highly Flammable/Very Toxic/Corrosive/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T); Highly toxic (T+)
• UN Number: 1992; 2922; 3179; UN3134
• German water hazard class: 3
• Hazard Class: 3; 4.1; 4.3; 6.1; 8
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 11-15-26/27/28-32-34-50/53; 11-19-23/24/25-32-36/37/38-50/53; 26/27/28-32-34-50/53; R:10-25
• Safety Statements: 16-26-36/37-45-61; 26-28-36/37/39-43-45-61; 26-28-36/37/39-45-60-61; 26-28-36/37/39-45-61; S:16-28-29-36/37/39-45
• EU Classification: FT2
• EU Hazard Identification Number: 4.1B
• Emergency Response Guidebook(ERG) Number: 134
• TSCA Listed: 是
• EU Index: not listed
• GHS Pictograms: GHS02; GHS05; GHS06; GHS09
• GHS Signal Word: Danger
• NFPA704:
  

  2

  3

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• GHS Hazard statements: H225-H301-H311-H314-H330-H335-H400-H411; H228-H260-H300-H310-H314-H330-H410; H228-H261-H300-H310-H330-H314-H318-H400-H410; H300-H310-H314-H330-H410
• GHS Precautionary statements: P210-P223-P231 + P232-P260-P370 + P378-P422; P210-P260-P273-P280-P284-P301 + P310; P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A; P260-P264-P273-P280-P284-P301 + P310
• 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
• RID/ADR: UN 1992 3/PG 2; UN 2922 8/PG 2; UN 3179 4.1/PG 2
• Supplemental Hazard Statements: Contact with acids liberates very toxic gas.; Contact with acids liberates very toxic gas., May form explosive peroxides.

Product Information

• Purity: ≥95%; ≥95.0% (RT); 90%; 95%
• Concentration: 1.0 M in THF; 5.0 M in 1 M NaOH
• Grade: purum; reagent grade
• Linear Formula: NaBH3CN

DETAILS

MP Biomedicals - 02199862

Aqueous solutions may be slightly hazy.

MP Biomedicals - 02156628

Purity: 90% Aqueous solutions may be slightly hazy.

Sigma Aldrich - 296945

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

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 - 71435

Other Notes
Review1,2; selctive reductions with NaCNBH3, modified with zinc chloride3; with zinc iodide4

Sigma Aldrich - 156159

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

Toronto Research Chemicals - S615500

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

• 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).