4,4'-Bis(methoxycarbonly)-2,2'-bipyridine Chemical Properties

Melting point:

208.0 to 212.0 °C

Boiling point:

440.8±45.0 °C(Predicted)

Density 

1.254±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

1.85±0.30(Predicted)

color 

White to Almost white

InChI

InChI=1S/C14H12N2O4/c1-19-13(17)9-3-5-15-11(7-9)12-8-10(4-6-16-12)14(18)20-2/h3-8H,1-2H3

InChIKey

HBWBVIDKBKOVEX-UHFFFAOYSA-N

SMILES

C1(C2=NC=CC(C(OC)=O)=C2)=NC=CC(C(OC)=O)=C1

CAS DataBase Reference

71071-46-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

WGK Germany 

3

HS Code 

29333990

4,4'-Bis(methoxycarbonly)-2,2'-bipyridine Usage And Synthesis

Uses

4,4'-Bis(methoxycarbonyl)-2,2'-bipyridine is a chemical reaction reagent or organic synthesis intermediate that can be used as a ligand in cross-coupling reactions, binding to metal ions and forming complexes. 4,4'-Bis(methoxycarbonyl)-2,2'-bipyridine has a constant value that maximizes the yield of the reaction and has luminescence, which can be used for voltammetry studies. The transfer of the chromophore or the catalyst can be optimized using this product. 4,4'-Bis(methoxycarbonyl)-2,2'-bipyridine provides a method for cross-coupling reactions using electrochemical studies and dichroism.

Synthesis

General procedure for the synthesis of methyl 2,2'-bipyridine-4,4'-dicarboxylate from methanol and 2,2'-bipyridine-4,4'-dicarboxylic acid: 2,2'-Bipyridine-4,4'-dicarboxylic acid (2.00 g, 8.10 mmol) was suspended in methanol (150 mL), and thionyl chloride (1492 μL, 20.48 mmol) was slowly added dropwise. The reaction mixture was stirred under reflux conditions overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was partitioned between dichloromethane (100 mL) and water (100 mL). The organic phase was washed three times with saturated aqueous sodium bicarbonate and dried over anhydrous sodium sulfate. Finally, the solvent was removed by reduced pressure distillation to give the white solid product methyl 2,2'-bipyridine-4,4'-dicarboxylate (2.00 g, 90% yield).

References

[1] Journal of the American Chemical Society, 2007, vol. 129, # 18, p. 5919 - 5925
[2] Tetrahedron Asymmetry, 2013, vol. 24, # 8, p. 515 - 525
[3] Inorganic Chemistry, 2018, vol. 57, # 15, p. 9316 - 9326
[4] Dalton Transactions, 2018, vol. 47, # 37, p. 13081 - 13087
[5] Journal of the American Chemical Society, 2016, vol. 138, # 51, p. 16815 - 16826

4,4'-Bis(methoxycarbonly)-2,2'-bipyridine(71071-46-0)Related Product Information

• Methyl anthranilate
• 2,2'-Bipyridine
• Dimethyl phthalate
• Dimethyl ether
• Methyl benzoate
• Dimethyl sebacate
• ETHANE
• Methyl formate
• Dimethyl fumarate
• 4,4'-Bipyridine
• DIPIPERIDINOMETHANE
• Dimethyl sulfoxide
• N,N-Dimethylformamide
• Methylparaben
• Dimethyl carbonate
• AcidEster
• DIBUTYL 2,2'-BIPYRIDINE-4,4'-DICARBOXYLATE
• Methyl chloroformate