Diethyl [2,2'-bipyridine]-6,6'-dicarboxylate

Name: Diethyl [2,2'-bipyridine]-6,6'-dicarboxylate
Brand: ChemScene
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CAS No. 65739-40-4
Cat. No. CS-0089094
Molecule weight300.31
Purity≥98%
MDL No.MFCD11042477

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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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Diethyl [2,2'-bipyridine]-6,6'-dicarboxylate|CS-0089094

Structure of 65739-40-4

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General Information

CAS No. 65739-40-4
Cat. No. CS-0089094
Purity ≥98%
MDL No. MFCD11042477
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₁₆N₂O₄
Molecular Weight 300.31
Synonym(s) Ethyl 6-(6-ethoxycarbonylpyridin-2-yl)pyridine-2-carboxylate
SMILES O=C(OCC)C=1N=C(C=CC1)C=2N=C(C=CC2)C(=O)OCC

Description

Diethyl [2,2'-bipyridine]-6,6'-dicarboxylate features a rigid bipyridyl core functionalized with ester groups at the 6,6' positions, enabling straightforward derivatization and coordination to transition metals. The ester moieties enhance solubility in organic solvents while maintaining structural integrity under standard handling conditions. This compound serves as a modular ligand scaffold for metal complex synthesis, particularly in catalytic systems requiring controlled sterics and electronic tuning.

Application

Diethyl [2,2'-bipyridine]-6,6'-dicarboxylate serves as a versatile bifunctional building block in transition metal catalysis and coordination chemistry. Its two ester groups enable straightforward derivatization to carboxylic acids or amides, while the bipyridine core provides robust chelation for Ru(II), Ir(III), and Pd(II) complexes. The molecule exhibits excellent bench stability, facilitates purification via standard chromatographic methods, and functions reliably in ligand synthesis for photoredox and cross-coupling applications.

Synthesis

Route1
- In-stock
  
  49669-22-9
- 64-17-5
- 201230-82-2
- ~87%
- In-stock
  
  65739-40-4
References
- El-Ghayoury; Ziessel Journal of Organic Chemistry, 2000 , vol. 65, # 23 p. 7757 - 7763
Route2
- 64-17-5
- In-stock
  
  4479-74-7
- ~83%
- In-stock
  
  65739-40-4
References
- Bozoklu, Guelay; Marchal, Claire; Gateau, Christelle; Pecaut, Jacques; Imbert, Daniel; Mazzanti, Marinella Chemistry - A European Journal, 2010 , vol. 16, # 21 p. 6159 - 6163

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 78.38
LogP 2.497
H_Acceptors 6
H_Donors 0
Rotatable_Bonds 5

Other Classifications

Catalysts and Ligands Ligands Pyridine Ligands Bipyridine 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

Key Words

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Diethyl [2,2'-bipyridine]-6,6'-dicarboxylate

CAS No. 65739-40-4

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