Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

Safety Information

296813

Sigma-Aldrich

Sodium cyanoborohydride solution

1.0 M in THF

Synonym(s):

Sodium borocyanohydride, Sodium cyanoborohydride, Sodium cyanotrihydroborate

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
NaBH3CN
CAS Number:
25895-60-7
Molecular Weight:
62.84
MDL number:
MFCD00003516
UNSPSC Code:
12352306
PubChem Substance ID:
24857879
NACRES:
NA.22

Quality Level

200

reaction suitability

reagent type: reductant

concentration

1.0 M in THF

solubility

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

density

0.915 g/mL at 25 °C

SMILES string

[Na+].[H][B-]([H])([H])C#N

InChI

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

InChI key

CVDUGUOQTVTBJH-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

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 e-amino groups of lysyl residues in proteins to the mono- and dimethyl derivatives.

Application

Reactant for:
  • Direct conversion of heterocyclic aldehydes to esters (oxidizing behavior)
  • Reductive amination reactions
  • Intramolecular reductive cyclization reactions
  • Reductions reactions
  • Preparation of dicyanoborate-based ionic liquids as hypergolic fluids for bipropellants
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.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3 - Water-react 1

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

-4.0 °F

Flash Point(C)

-20 °C

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Poisonous substance

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Metal hydrides
Hazardous rank I
1st spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

296813-800ML:4548173131788
296813-VAR:
296813-100ML:4548173131771
296813-BULK:
296813-PZ:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBQ6541
SHBN7864
SHBJ9547
SHBF6588V
65896PMV

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Sodium cyanoborohydride-a highly selective reducing agent for organic functional groups.
Clinton F.
Synthesis, 3, 135-146 (1975)
Preparation of colloidal gold particles of various sizes using sodium borohydride and sodium cyanoborohydride.
R G DiScipio
Analytical biochemistry, 236(1), 168-170 (1996-04-05)
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)
Shinsuke Sando et al.
Bioorganic & medicinal chemistry letters, 13(16), 2633-2636 (2003-07-23)
We report here that unprotected carbohydrates (maltose, lactose, cellobiose, and maltoheptaose) can be attached to the aminoalkylated oligonucleotides under mild reductive-amination conditions (aqueous borate buffer, pH 8.0, NaBH(3)CN, 60 degrees C) without notable side reactions. Quadruplex-forming G-rich oligonucleotide, 5'-aminoalkyl d(TGGGGT)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service