diethyl 2,2'-bipyridine-5,5'-dicarboxylate Chemical Properties

Melting point:

145-147 °C

Boiling point:

428.9±45.0 °C(Predicted)

Density 

1.201±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

1.99±0.32(Predicted)

color 

White to Almost white

InChI

InChI=1S/C16H16N2O4/c1-3-21-15(19)11-5-7-13(17-9-11)14-8-6-12(10-18-14)16(20)22-4-2/h5-10H,3-4H2,1-2H3

InChIKey

IUNBUYCOAQHBMC-UHFFFAOYSA-N

SMILES

C1(C2=NC=C(C(OCC)=O)C=C2)=NC=C(C(OCC)=O)C=C1

Safety Information

HS Code 

2933.39.9200

diethyl 2,2'-bipyridine-5,5'-dicarboxylate Usage And Synthesis

Uses

Diethyl bipy55'DC is an inhibitor of collagen proline 4-hydroxylases (CP4Hs) with antifibrotic and anti-metastatic activities. Diethyl bipy55'DC can inhibit CP4H activity in cultured cells at concentrations that do not cause iron deficiency[1].

Synthesis

General procedure for the synthesis of diethyl [2,2'-bipyridine]-5,5'-dicarboxylate from ethanol and 2,2'-bipyridine-5,5'-dicarboxylic acid: 2,2'-bipyridine-5,5'-dicarboxylic acid (200 mg, 0.82 mmol) and anhydrous ethanol (13 mL) were added to a dry flask with stirring under an ice bath. Thionyl chloride (1.3 mL) was slowly added dropwise, followed by installation of a reflux condenser and heating to reflux. After 24 hours of reaction, the reaction mixture was cooled in an ice bath and saturated sodium carbonate solution (20 mL) was added dropwise to quench the reaction. The aqueous phase was extracted with dichloromethane (4 x 20 mL), the organic phases were combined and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 1:1 dichloromethane/hexane solvent mixture of 3% acetone) to afford diethyl [2,2'-bipyridyl]-5,5'-dicarboxylate (190 mg, 77% yield) as a white solid.1H NMR (500 MHz, CDCl3) δ 9.32 (dd, J = 0.5, 2.0 Hz, 1H), 8.59 (dd, J = 0.5, 8.5 Hz, 1H), 8.46 (dd, J = 2.0, 8.5 Hz, 1H), 4.47 (q, J = 7.5 Hz, 2H), 1.46 (t, J = 7.5 Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 165.2, 158.3, 150.6, 138.1, 126.6, 121.3, 61.6, 14.3; HRMS (ESI) m/z 301.1193 [C16H17N2O4 (M + H)+ calculated value 301.1183].

References

[1] Vasta J D, et al. Selective inhibition of collagen prolyl 4-hydroxylase in human cells[J]. ACS chemical biology, 2016, 11(1): 193-199. DOI:10.1021/acschembio.5b00749

diethyl 2,2'-bipyridine-5,5'-dicarboxylate(1762-46-5)Related Product Information

• 2,2'-Bipyridine-5,5'-dicarboxylic acid
• DIMETHYL 2,2'-BIPYRIDINE-6,6'-DICARBOXYLATE
• 2,2'-Bipyridine-3,3'-dicarboxylic acid dimethyl ester
• 4,4'-Bis(methoxycarbonly)-2,2'-bipyridine
• 2,2'-Bipyridine-3,3'-dicarboxylic acid
• diethyl [2,2'-bipyridine]-3,3'-dicarboxylate
• 3,3'-DIMETHYL-2,2'-BIPYRIDINE
• 2,2'-Bipyridine-4,4'-dicarboxylic acid
• 5,5'-DIMETHYL-2,2'-DIPYRIDYL
• 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine
• 6,6'-Dimethyl-2,2'-dipyridyl
• [2,2'-Bipyridine]-5,5'-diMethanol
• 4,4'-Dimethyl-2,2'-bipyridyl
• 2,2'-Bipyridyl-5,5'-dialdehyde
• DIETHYL 2,2'-BIPYRIDINE-6,6'-DICARBOXYLATE
• 5,5'-diMethoxycarbonyl-2,2'-bipyridine
• 6,6′-bis(hydroxymethyl)-2,2′-bipyridine
• 2,2'-BIPYRIDINE-6,6'-DICARBOXYLIC ACID