6-Methyl-2-pyridinecarboxylic acid Chemical Properties

Melting point:

130 °C

Boiling point:

100°C/4.5mm

Density 

1.230±0.06 g/cm3(Predicted)

Flash point:

100°C/4.5mm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Soluble in water

form 

powder to crystal

pka

pK1:5.83 (25°C)

color 

White to Almost white

InChI

InChI=1S/C7H7NO2/c1-5-3-2-4-6(8-5)7(9)10/h2-4H,1H3,(H,9,10)

InChIKey

LTUUGSGSUZRPRV-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

934-60-1(CAS DataBase Reference)

NIST Chemistry Reference

6-Methyl picolinic acid(934-60-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

6-Methyl-2-pyridinecarboxylic acid Usage And Synthesis

Chemical Properties

White to beige powder

Uses

Pharmacological activity studied in regard to:

• Interactions of carrier ligands of antidiabetic metal complexes with human serum albumin
• Ability to chelate metalloenzyme inhibitors
• Interactions of insulin-mimetic zinc(II) complexes with cell constituents

• Synthesis of inhibitors of human 11β -hydroxysteroid dehydrogenase type 1
• Lewis base organocatalysts for stereoselective hydrosilylation reactions

General Description

6-Methylpyridine-2-carboxylic acid (2-carboxy-6-methylpyridine, 6-methylpicolinic acid) is a heterocyclic building block.

Synthesis

Step 1: 2,6-dimethylpyridine (10.71 g, 0.1 mol) was dissolved in 500 mL of deionized water, stirred and heated to 60 °C. Subsequently, potassium permanganate (KMnO4, 23.7 g, 0.15 mol) was added in ten portions, with an interval of 30 min between each addition. The temperature was strictly controlled at about 60°C during the reaction, which lasted for 5 h and then stopped. Immediately after completion of the reaction, the insoluble impurities were removed by filtration. The filtrate was adjusted to pH=5 and then extracted with ethyl acetate. The organic phase was collected, concentrated under reduced pressure and finally recrystallized from ethanol to obtain 6-methyl-2-pyridinecarboxylic acid (10.3 g, 75% yield). In this step, the effects of different reaction conditions (e.g., equivalents of KMnO4 of 1, 1.5 and 2, aqueous potassium permanganate solution of different pH, temperature and molar ratio) on the reaction were investigated by orthogonal tests, and the optimal reaction conditions were determined to be neutral aqueous potassium permanganate solution with a dosage of 1.5 equivalents of KMnO4.

References

[1] Patent: CN105294552, 2016, A. Location in patent: Paragraph 0047; 0048; 0049; 0050
[2] Chemische Berichte, 1900, vol. 33, p. 1226
[3] Chemische Berichte, 1900, vol. 33, p. 1081
[4] Chemische Berichte, 1900, vol. 33, p. 1230
[5] Journal of Organic Chemistry, 1949, vol. 14, p. 14,17

6-Methyl-2-pyridinecarboxylic acid(934-60-1)Related Product Information

• Kresoxim-methyl
• Methanol
• Basic Violet 1
• Acetonitrile
• 2-Picolinic acid
• Methyl acrylate
• 2,6-Lutidine
• Methylparaben
• Chromium picolinate
• Paraquat dichloride
• 4-Methylpyridine
• Zinc picolinate
• Methyl acetate
• Methyl
• Dimethyl 2,6-Pyridinedicarboxylate
• Pyrroloquinoline quinone
• Pyridine-2,6-dicarboxylic acid
• Chelidamic acid