296813

Sigma-Aldrich

Sodium cyanoborohydride solution

1.0 M in THF

Synonym(s):
Sodium borocyanohydride, Sodium cyanoborohydride, Sodium cyanotrihydroborate
Linear Formula:
NaBH3CN
CAS Number:
Molecular Weight:
62.84
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

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.

Packaging

100, 800 mL in Sure/Seal™

Signal Word

Danger

Supp Hazards

EUH018 - EUH019

RIDADR

UN 1992 6.1(3) / PGII

WGK Germany

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Certificate of Analysis
Certificate of Origin
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)
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)
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)
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)...

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

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.