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296813

Sigma-Aldrich

Sodium cyanoborohydride solution

1.0 M in THF

Synonym(s):
Sodium borocyanohydride, Sodium cyanoborohydride, Sodium cyanotrihydroborate
Linear Formula:
NaBH3CN
CAS Number:
Molecular Weight:
62.84
MDL number:
PubChem Substance ID:

Quality Level

reaction suitability

reagent type: reductant

concentration

1.0 M in THF

solubility

THF: soluble(lit.)
alcohol: soluble(lit.)
hydrocarbons: insoluble(lit.)
water: soluble(lit.)

density

0.915 g/mL at 25 °C

SMILES string

[Na+].[H][B-]([H])([H])C#N

InChI

1S/CH3BN.Na/c2-1-3;/h2H3;/q-1;+1

InChI key

CVDUGUOQTVTBJH-UHFFFAOYSA-N

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General description

Sodium cyanoborohydride is a versatile reducing agent stable in aqueous solution at pH 7.2. It is a weaker reducing agent as compared to NaBH4. It effectively reduces Schiff bases. NaCNBH4 participates in the reductive methylation for the efficient and selective conversion of the e-amino groups of lysyl residues in proteins to the mono- and dimethyl derivatives.

Application

Reactant for:
  • Direct conversion of heterocyclic aldehydes to esters (oxidizing behavior)
  • Reductive amination reactions
  • Intramolecular reductive cyclization reactions
  • Reductions reactions
  • Preparation of dicyanoborate-based ionic liquids as hypergolic fluids for bipropellants
Sodium cyanoborohydride may be used in the following studies:
  • As reducing agent for the in vitro radiolabeling of proteins by reductive alkylation.
  • Reduction of aldehydes and ketones.
  • Selective deoxygenation of aldehydes and ketones.
  • Preparation of colloidal gold particles of varying sizes.

Packaging

100, 800 mL in Sure/Seal™

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - Water-react 1

Supplementary Hazards

Storage Class Code

4.3 - Hazardous materials, which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

-4.0 °F

Flash Point(C)

-20 °C

Certificate of Analysis

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Certificate of Origin

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