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71435

Sigma-Aldrich

Sodium cyanoborohydride

purum, ≥95.0% (RT)

Synonym(s):

Sodium cyanotrihydridoborate

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About This Item

Linear Formula:
NaBH3CN
CAS Number:
25895-60-7
Molecular Weight:
62.84
Beilstein:
4152656
EC Number:
247-317-2
MDL number:
MFCD00003516
UNSPSC Code:
12352000
PubChem Substance ID:
329763275

grade

purum

Assay

≥95.0% (RT)

reaction suitability

reagent type: reductant

mp

>242 °C (dec.) (lit.)

solubility

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

SMILES string

[Na+].[BH3-]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 ε-amino groups of lysyl residues in proteins to the mono- and dimethyl derivatives.
Review on sodium cyanoborohydride has been reported. It participates in selective reductions with NaCNBH3, modified with zinc chloride, with zinc iodide.

Application

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.

Other Notes

Review; selctive reductions with NaCNBH3, modified with zinc chloride; with zinc iodide

Signal Word

Danger

Hazard Classifications

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

Supplementary Hazards

EUH032

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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S. Kim et al.
The Journal of Organic Chemistry, 50, 1927-1927 (1985)
C.F. Lane
Synthesis, 135-135 (1975)
C.K. Lau et al.
The Journal of Organic Chemistry, 51, 3038-3038 (1986)
Radiolabeling of proteins by reductive alkylation with [14C]formaldehyde and sodium cyanoborohydride.
D Dottavio-Martin et al.
Analytical biochemistry, 87(2), 562-565 (1978-07-01)
Labeling of proteins by reductive methylation using sodium cyanoborohydride.
N Jentoft et al.
The Journal of biological chemistry, 254(11), 4359-4365 (1979-06-10)
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