[2,2'-Bipyridine]-5,5'-dicarboxaldehyde

Name: [2,2'-Bipyridine]-5,5'-dicarboxaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 135822-72-9
Cat. No. CS-W004565
Purity≥97%
MDL No.None

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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+
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[2,2'-Bipyridine]-5,5'-dicarboxaldehyde|CS-W004565

Structure of 135822-72-9

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General Information

CAS No. 135822-72-9
Cat. No. CS-W004565
Purity ≥97%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₈N₂O₂
Molecular Weight 212.20
Synonym(s) 2,2'-BIPYRIDYL-5,5'-DIALDEHYDE
SMILES O=CC1=CC=C(C2=CC=C(C=O)C=N2)N=C1

Description

This bipyridine derivative features two aldehyde groups positioned at the 5 and 5′-sites, enabling precise coordination in metal-ligand assemblies. The electron-deficient pyridine rings enhance binding affinity for transition metals, while the aldehyde functionalities facilitate post-modification via reductive amination or hydrazone formation. Ideal for constructing redox-active scaffolds in catalysis and molecular sensing applications.

Application

[2,2'-Bipyridine]-5,5'-dicarboxaldehyde serves as a versatile bifunctional building block in coordination chemistry and catalysis. Its two aldehyde groups enable facile imine formation and derivatization, while the rigid bipyridine core provides strong metal-chelating capability. The molecule exhibits excellent bench stability and compatibility with standard synthetic protocols, facilitating the construction of functionalized ligands, porous materials, and redox-active scaffolds for applications in homogeneous catalysis and molecular electronics.

Synthesis

Route1
- In-stock
  
  63361-65-9
- ~14%
- In-stock
  
  135822-72-9
References
- Narayan; Geetha; Nakmanovich; Ehrenfreund; Eichen Journal of Physical Chemistry B, 2001 , vol. 105, # 32 p. 7671 - 7677
Route2
- 153305-75-0
- ~%
- In-stock
  
  135822-72-9
References
- Narayan; Geetha; Nakmanovich; Ehrenfreund; Eichen Journal of Physical Chemistry B, 2001 , vol. 105, # 32 p. 7671 - 7677

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 59.92
LogP 1.7686
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Catalysts and Ligands Ligands Pyridine Ligands Bipyridine Ligands

Material Science Polymer/Macromolecule Reagents Dendrimer Building Blocks

Catalysis Nitrogen-Donor Ligands Pyridine Ligands

Catalysis Nitrogen-Donor Ligands Bipyridine Ligands, Terpyridine Ligands

Material Science Material Building Blocks Covalent Organic Frameworks (COFs) Linkers Aldehyde Linkers

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

Material Science Polymer/Macromolecule Reagents Covalent Organic Frameworks (COFs) Linkers Aldehyde Linkers

Key Words

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[2,2'-Bipyridine]-5,5'-dicarboxaldehyde

CAS No. 135822-72-9

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