6-Chloropicolinic acid Chemical Properties

Melting point:

190-191°C

Boiling point:

241.15°C (rough estimate)

Density 

1.3768 (rough estimate)

refractive index 

1.5870 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol

pka

3.27±0.10(Predicted)

form 

Crystalline Powder

color 

White to cream to tan

Water Solubility 

3.40g/L(temperature not stated)

λmax

294nm(EtOH)(lit.)

BRN 

115849

InChIKey

ZLKMOIHCHCMSFW-UHFFFAOYSA-N

CAS DataBase Reference

4684-94-0(CAS DataBase Reference)

EPA Substance Registry System

6-Chloropicolinic acid (4684-94-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

2

RTECS 

TJ7535000

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

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6-Chloropicolinic acid Usage And Synthesis

Chemical Properties

Off-white Plates

Uses

6-Chloropyridine-2-carboxylic Acid is an intermediate of Sorafenib b(S676850), a multiple kinase inhibitor targeting both RAF kinase and receptor tyrosine kinases that promote angiogensis. Antineoplastic.

Synthesis

General procedure for the synthesis of 6-chloropyridine-2-carboxylic acid from 2-chloro-6-trichloromethylpyridine: 2-chloro-6-trichloromethylpyridine (115.5 g, 0.5 mol) and 98% concentrated sulfuric acid (60 g, 0.6 mol) were added sequentially to a 500 mL three-neck flask equipped with a thermometer. The reaction mixture was heated to 100 °C and maintained at this temperature for 8 hours. Upon completion of the reaction, the reaction solution was cooled to 60 °C and neutralized by slow dropwise addition of 27% ammonia until the pH reached 7. Subsequently, the reaction mixture was cooled to room temperature with continuous stirring to precipitate the solid. The white solid product was collected by diafiltration in 90% yield with a melting point of 192-193 °C.

References

[1] Patent: CN108530351, 2018, A. Location in patent: Paragraph 0011; 0026; 0027

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