2-Chloro-6-methylnicotinic acid Chemical Properties

Melting point:

162-164 °C (lit.)

Boiling point:

163 °C / 22mmHg

Density 

1.3246 (rough estimate)

refractive index 

1.5560 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Crystalline Powder

pka

2.28±0.28(Predicted)

color 

White to yellow to beige

BRN 

473070

InChI

InChI=1S/C7H6ClNO2/c1-4-2-3-5(7(10)11)6(8)9-4/h2-3H,1H3,(H,10,11)

InChIKey

ACQXHCHKMFYDPM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

30529-70-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:2-Chloro-6-methylnicotinic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chloro-6-methylnicotinic acid Usage And Synthesis

Chemical Properties

white to yellow crystalline powder

Uses

2-Chloro-6-methylpyridine-3-carboxylic acid (2-Chloro-6-methylnicotinic acid) may be used in the synthesis of 6-methyl-2-thiophenoxynicotinic acid, required for the preparation of europium complex for staining the nucleolus of NIH 3T3, HeLa and HDF cells.

General Description

2-Chloro-6-methylpyridine-3-carboxylic acid (2-Chloro-6-methylnicotinic acid) is a nicotinic acid derivative.

Synthesis

General procedure for the synthesis of 2-chloro-6-methylnicotinic acid from 2-chloro-6-methyl-3-pyridinecarbonitrile: First, 2-chloro-3-cyano-6-methylpyridine (3.05 g) was dissolved in 75% sulfuric acid (10 mL). The reaction mixture was stirred at 110 °C for 2 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature and slowly added dropwise to ice water. After stirring the ice-water mixture for 10 minutes, the precipitated crystals were collected by filtration and dried to give 2.91 g of 2-chloro-6-methylnicotinic acid in 85% yield. Next, the resulting 2-chloro-6-methylnicotinic acid (2.91 g) was mixed with 28% aqueous ammonia solution (35 mL) and placed in an autoclave and reacted at 170 °C for 40 hours. At the end of the reaction, the reaction solution was cooled to room temperature and the ammonia was removed by distillation under reduced pressure. The precipitated crystals were collected by filtration, washed with water and air-dried to give 1.91 g of amino-6-methylnicotinic acid in 74% yield. The total yield of the whole synthesis process was 62.9%.

References

[1] Patent: TW2016/509, 2016, A. Location in patent: Page/Page column 6

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