5-Methylpyridine-2,3-dicarboxylic acid Chemical Properties

Boiling point:

436.2±45.0 °C(Predicted)

Density 

1.460

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

5.41±0.20(Predicted)

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C8H7NO4/c1-4-2-5(7(10)11)6(8(12)13)9-3-4/h2-3H,1H3,(H,10,11)(H,12,13)

InChIKey

JPIJMXOJEHMTPU-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=NC=C(C)C=C1C(O)=O

CAS DataBase Reference

53636-65-0

EPA Substance Registry System

2,3-Pyridinedicarboxylic acid, 5-methyl- (53636-65-0)

5-Methylpyridine-2,3-dicarboxylic acid Usage And Synthesis

Chemical Properties

White or light yellow crystalline powder

Uses

5-Methoxymethylpyridine-2,3-dicarboxylic acid is used in the preparation of herbicides of the class imidazolinones.

Synthesis

A) 3-methyl-8-hydroxyquinoline (15.9 g, 0.10 mol) is dissolved in dichloromethane and slowly added dropwise to 70% nitric acid (126 g, 1.8 mol) at 80°C to 100°C over a period of 1 hour while stirring is maintained. The gases generated during the reaction are scrubbed and vented. The reaction mixture is then heated at 100°C to 105°C for 4 h. After cooling to 85°C, the reaction mixture is treated with 88% formic acid (85%-95% concentration) for 20 min and continued heating at 85°C to 95°C for 0.5 h. The reaction solution is cooled to 0.5°C. The reaction solution was cooled to 0°C, stirred for 1 hour and filtered. The resulting solid was washed with acetone and dried to give 10.6 g of 5-methyl-2,3-pyridinedicarboxylic acid (58.6% yield), which was analyzed by HPLC for 97.4% purity.

References

[1] Patent: US5371229, 1994, A
[2] Patent: US5371229, 1994, A
[3] Journal of the Chemical Society, 1956, p. 4433,4437
[4] Synthesis, 1989, # 11, p. 880 - 882

5-Methylpyridine-2,3-dicarboxylic acid(53636-65-0)Related Product Information

• 4-Methylpyridine
• 2-Chloro-5-chloromethylpyridine
• Ethyl 2-(Chlorosulfonyl)acetate
• 2,6-Lutidine
• 2,5-PYRIDINEDICARBOXYLIC ACID
• Azamethiphos
• 2,4,6-Collidine
• Folic acid
• Quinolinic acid
• 2,3-Lutidine
• OXALIC ACID
• Citric acid
• Ascoric Acid
• 5-ETHYLPYRIDINE-2,3-DICARBOXYLIC ACID
• 5-Ethylpyridine-2,3-dicarboxylic acid diethyl ester
• 5-Methoxymethyl-2,3-pyridinedicarboxylic acid
• 2,3-PYRIDINEDICARBOXYLIC ACID, 5-(TRIFLUOROMETHYL)-, DIETHYL ESTER
• 5-Methylpyridine-2,3-dicarboxylatediethylester