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Merck

156159

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
UNSPSC Code:
12352306
NACRES:
NA.22
PubChem Substance ID:
24849595
EC Number:
247-317-2
Beilstein/REAXYS Number:
4152656
MDL number:
MFCD00003516
Assay:
95%
Form:
powder

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InChI key

CVDUGUOQTVTBJH-UHFFFAOYSA-N

InChI

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

SMILES string

[Na+].[BH3-]C#N

grade

reagent grade

assay

95%

form

powder

reaction suitability

reagent type: reductant

mp

>242 °C (dec.) (lit.)

Quality Level

300

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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.

signalword

Danger

supp_hazards

EUH032

Storage Class

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

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS9916
SHBS6957
STBK9683
STBL3836
STBL3546

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Synthetic Communications, 24, 701-701 (1994)
Tetrahedron Letters, 35, 2775-2775 (1994)
Aldrichimica Acta, 8, 3-10 (1975)
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)
The Journal of Organic Chemistry, 55, 2552-2552 (1990)
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