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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/REAXYS Number:
4152656
EC Number:
247-317-2
MDL number:
MFCD00003516
UNSPSC Code:
12352306
PubChem Substance ID:
24849595
NACRES:
NA.22

grade

reagent grade

Quality Level

300

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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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

158.0 °F - closed cup

flash_point_c

70 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL2038
STBL2046
STBL0646
STBL0638
STBL0639

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The Journal of Organic Chemistry, 55, 2552-2552 (1990)
Aldrichimica Acta, 8, 3-10 (1975)
Synthetic Communications, 24, 701-701 (1994)
Tetrahedron Letters, 35, 2775-2775 (1994)
Wang, Z. et al.
Inorganic Chemistry, 36, 629-629 (1997)
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