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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/REAXYS Number:
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.[1] It is a weaker reducing agent as compared to NaBH4. It effectively reduces Schiff bases.[2] 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.[2]
Review on sodium cyanoborohydride has been reported.[3][4] It participates in selective reductions with NaCNBH3, modified with zinc chloride,[5] with zinc iodide.[6]

Application

Sodium cyanoborohydride may be used in the following studies:
  • As reducing agent for the in vitro radiolabeling of proteins by reductive alkylation.[1]
  • Reduction of aldehydes and ketones.[7]
  • Selective deoxygenation of aldehydes and ketones.[8]
  • Preparation of colloidal gold particles of varying sizes.[9]

Other Notes

Review[3][4]; selctive reductions with NaCNBH3, modified with zinc chloride[5]; with zinc iodide[6]

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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

supp_hazards

EUH032

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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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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