6-Cyano-2,2'-bipyridine

Name: 6-Cyano-2,2'-bipyridine
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CAS No. 4392-85-2
Cat. No. CS-0086393
Molecule weight181.20
Purity≥98%
MDL No.MFCD07364147

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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General Information

CAS No. 4392-85-2
Cat. No. CS-0086393
Purity ≥98%
MDL No. MFCD07364147
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₇N₃
Molecular Weight 181.20
Synonym(s) 6-Cyano-2,2'-bipyridyl
SMILES N#CC1=NC(=CC=C1)C2=NC=CC=C2

Description

6-Cyano-2,2'-bipyridine features a cyano group at the 6-position of the bipyridine scaffold, enhancing electron-withdrawing character and enabling strong metal coordination. This structural motif facilitates formation of stable complexes with transition metals, particularly in catalytic systems requiring redox-active ligands. The molecule exhibits high thermal stability and compatibility with diverse reaction conditions.

Application

6-Cyano-2,2'-bipyridine serves as a versatile ligand scaffold in transition metal catalysis, particularly in palladium- and copper-mediated cross-coupling reactions. Its electron-deficient bipyridine core enhances metal coordination strength, while the nitrile group provides orthogonal functionality for further derivatization. The compound exhibits excellent bench stability and facilitates efficient catalyst formation in C–C and C–heteroatom bond-forming processes.

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

TPSA 49.57
LogP 2.01528
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Catalysts and Ligands Ligands Pyridine Ligands Bipyridine Ligands

Material Science Material Building Blocks Ligands for Functional Metal Complexes Bipyridine Ligands, Terpyridine Ligands

Material Science Organic-Inorganic Hybrid Materials Metal Organic Frameworks (MOF) Raw Materials Organic Linker Molecules

Material Science Polymer/Macromolecule Reagents Metal Organic Frameworks (MOF) Raw Materials Organic Linker Molecules

Catalysis Nitrogen-Donor Ligands Pyridine Ligands

Catalysis Nitrogen-Donor Ligands Bipyridine Ligands, Terpyridine Ligands

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6-Cyano-2,2'-bipyridine

CAS No. 4392-85-2

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