DIMETHYL PYRIDINE-2,5-DICARBOXYLATE Chemical Properties

Melting point:

213-217 °C(lit.)

Boiling point:

302.9±22.0 °C(Predicted)

Density 

1.231±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Dichloromethane, Ethyl Acetate

pka

-0.35±0.10(Predicted)

Appearance

White to off-white Solid

Water Solubility 

Soluble in Dichloromethane and Ethyl Acetate. Insoluble in water.

BRN 

172251

InChI

InChI=1S/C9H9NO4/c1-13-8(11)6-3-4-7(10-5-6)9(12)14-2/h3-5H,1-2H3

InChIKey

TUGSJNQAIMFEDY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

881-86-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933399990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

DIMETHYL PYRIDINE-2,5-DICARBOXYLATE Usage And Synthesis

Uses

Intermediate for the synthesis of potent antitumor agents.

Uses

It is the intermediate in the synthesis of potent antitumor agents.

General Description

Dimethyl 2,5-pyridine dicarboxylate can be prepared from 2,5-pyridinedicarboxylic acid.

Synthesis

Oxalyl chloride (60.96 g, 480 mmol) was slowly added dropwise over 20 min to a suspension of 2,5-pyridinedicarboxylic acid (20 g, 120 mmol) in dichloromethane (396 mL) and N,N-dimethylformamide (DMF, 6.6 mL). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure by rotary evaporator and the residue was azeotroped with toluene to remove residual water. The residue was dissolved in methanol (276 mL) pre-cooled to 0 °C and stirred for 15 min. Upon completion of the reaction, the solution was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. The organic phase was washed sequentially with saturated aqueous sodium bicarbonate solution, deionized water and saturated brine. Some of the product was collected as a white precipitate. The organic phase was separated, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give methyl 2,5-pyridinedicarboxylate as a white solid (Yield: 22.93 g, 98% yield). It was analyzed by liquid chromatography-mass spectrometry (LCMS, Method B) with a retention time (R t) of 2.48 min and a molecular ion peak [M + H] + = 196.

References

[1] Patent: WO2009/85983, 2009, A1. Location in patent: Page/Page column 65
[2] Molecules, 2014, vol. 19, # 1, p. 102 - 121
[3] European Journal of Organic Chemistry, 2013, # 3, p. 541 - 549
[4] Tetrahedron Letters, 2005, vol. 46, # 6, p. 967 - 969
[5] Patent: US2007/231300, 2007, A1. Location in patent: Page/Page column 13-14

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