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156159

Sigma-Aldrich

Sodium cyanoborohydride

reagent grade, 95%

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:
12352306
PubChem Substance ID:
24849595
NACRES:
NA.22

grade

reagent grade

Assay

95%

form

powder

reaction suitability

reagent type: reductant

mp

>242 °C (dec.) (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, also known as sodium cyanotrihydridoborate, is a mild reducing agent that is stable in acidic conditions. It is widely used in the selective reduction of aryl aldehydes and ketones.

Application

Reagent for selective reductions.
Sodium cyanoborohydride is used as a reagent: 
  • To convert the amino-functional Si3N4 surface to a reactive surface with aldehyde groups.
  • For coupling amino-modified oligonucleotide probes.
  • In the synthesis of a novel phenolate-bridged dilanthanum(III) complex of interest as a model for metalloproteins.
  • In the reductive amination of aldehydes and ketones, and in the reductive alkylation of amines.

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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)

158.0 °F - closed cup

Flash Point(C)

70 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Aldrichimica Acta, 8, 3-10 (1975)
Tetrahedron Letters, 35, 2775-2775 (1994)
Synthetic Communications, 24, 701-701 (1994)
Immobilization of oligonucleotide probes on Si3N4 surface and its application to genetic field effect transistor
Toshiya S, et al.
Materials Science and Engineering, C, 24, 827-832 (2004)
Reductive deoxygenation of aryl aldehydes and ketones and benzylic, allylic, and tertiary alcohols by zinc iodide-sodium cyanoborohydride
CK L, et al.
The Journal of Organic Chemistry, 51, 3038-3043 (1986)
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