dimethyl 4-chloropyridine-2,6-dicarboxylate Chemical Properties

Melting point:

168℃

Boiling point:

355℃

Density 

1.347

Flash point:

169℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Solid

pka

-2.40±0.10(Predicted)

color 

Pale yellow

Water Solubility 

Slightly soluble in water.

Safety Information

Risk Statements 

20/21/22

Safety Statements 

24/25-36/37

HS Code 

29333990

dimethyl 4-chloropyridine-2,6-dicarboxylate Usage And Synthesis

Chemical Properties

White solid

Uses

Employed as an important intermediate for raw material for organic synthesis, agrochemical, pharmaceutical and dyestuff field

Synthesis

The general procedure for the synthesis of methyl 4-chloro-2,6-dipyridinecarboxylate from methanol and 4-oxo-1,4-dihydro-2,6-pyridinedicarboxylic acid was as follows: phosphorus pentachloride (PCl5, 11.8 g, 56.8 mmol) was slowly added to chloroform containing 4-oxo-1,4-dihydro-2,6-pyridinedicarboxylic acid (2.5 g, 13.8 mmol) ( CHCl3, 30 mL) solution. The reaction mixture was refluxed for 3 days. Upon completion of the reaction, it was cooled to 0°C and methanol (MeOH) was added dropwise until gas escape ceased. Subsequently, the solution was stirred at room temperature for 2 hours and then concentrated. To the concentrate, saturated aqueous sodium bicarbonate (NaHCO3) was added and the pH was adjusted to 7. The organic layer was separated, dried over anhydrous sodium sulfate (Na2SO4), filtered and the solvent was evaporated under vacuum. The residue was purified by column chromatography (eluent: cyclohexane/ethyl acetate, 8:2) to afford the target product methyl 4-chloro-2,6-dipyridinecarboxylate (2.57 g, 93% yield) as a white solid. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3) and 13C NMR (100 MHz, CDCl3).

References

[1] Tetrahedron, 2015, vol. 71, # 33, p. 5321 - 5336
[2] Chemistry - An Asian Journal, 2013, vol. 8, # 11, p. 2685 - 2690
[3] Patent: US2015/361116, 2015, A1. Location in patent: Paragraph 0171
[4] Journal of Organic Chemistry, 2003, vol. 68, # 7, p. 2741 - 2747
[5] Tetrahedron Letters, 1986, vol. 27, # 31, p. 3635 - 3638

dimethyl 4-chloropyridine-2,6-dicarboxylate(5371-70-0)Related Product Information

• 6-Methyl-2-pyridinecarboxylic acid
• 4-Chloropyridine-2-carboxylic acid
• 2,6-Pyridinedicarboxylic acid monomethyl ester
• Dimethyl 2,6-Pyridinedicarboxylate
• (4-CHLORO-PYRIDIN-2-YL)-METHANOL
• Pyridine-2,6-dicarboxylic acid
• Methyl 4-chloropicolinate
• 4-CHLOROPICOLINALDEHYDE
• dimethyl 4-chloropyridine-2,6-dicarboxylate
• 4-Chloro-2,6-dimethylpyridine
• 4-CHLORO-PYRIDINE-2,6-DICARBOXYLIC ACID
• 4-Chloro-6-methylpyridine-2-carboxylic acid
• (4-CHLORO-6-METHYL-PYRIDIN-2-YL)-METHANOL
• Di-tert.-butyl 4-chloro-2,6-pyridinedicarboxylate
• 6-FORMYL-2-PYRIDINE CARBOXYLIC ACID METHYL ESTER
• METHYL-6-HYDROXYMETHYL-2-CARBOXYLATE PYRIDINE
• methyl 6-methylpyridine-2-carboxylate
• METHYL 4-CHLORO-6-(HYDROXYMETHYL)PICOLINATE