5,6-Dichloronicotinic acid Chemical Properties

Melting point:

164-168 °C(lit.)

Boiling point:

342.1±37.0 °C(Predicted)

Density 

1.612±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

2.87±0.10(Predicted)

form 

Powder

color 

White to beige to tan

BRN 

383740

InChI

InChI=1S/C6H3Cl2NO2/c7-4-1-3(6(10)11)2-9-5(4)8/h1-2H,(H,10,11)

InChIKey

RNRLTTNKVLFZJS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

41667-95-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

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

5,6-Dichloronicotinic acid Usage And Synthesis

Chemical Properties

white to off-white crystalline powder

Uses

5,6-Dichloronicotinic acid is a dihalonicotinic acid. It is used in the preparation of 5-chloro-6-iodonicotinic acid by iodine displacement.

Application

5,6-Dichloronicotinic acid is a compound that can be synthesized by reacting methyl ketones with chloroacetic acid. It is used in the synthesis of maleic anhydride and has been shown to inhibit the catalysis of acetylcholine chloride. It has also been shown to have an inhibitory effect on Alzheimer's disease. The kinetic mechanism for this inhibition occurs through the hydrolysis step of 5,6-Dichloronicotinic acid by magnesium chloride in hexane solution. The reactive acylation reaction proceeds when it reacts with acetic anhydride in the presence of pyridine.

Synthesis

The general procedure for the synthesis of 5,6-dichloropyridine-3-carboxylic acid from 5,6-dichloronicotinic acid ethyl ester was as follows: in a solvent mixture of tetrahydrofuran (THF), methanol (MeOH) and water (50 mL, 4:1:1, v/v/v), ethyl 5,6-dichloronicotinic acid ethyl ester (1.0 g, 4.5 mmol) and aqueous sodium hydroxide 2N solution (6.75 mL, 13.5 mmol). The reaction mixture was stirred at room temperature for 0.5 hours. Upon completion of the reaction, the mixture was concentrated to remove the organic solvent. Subsequently, the mixture was acidified with 2N hydrochloric acid to a pH of about 2. The acidified mixture was extracted with ether (30 mL x 3). The organic layers were combined, washed with water (50 mL x 3), dried over anhydrous sodium sulfate, and concentrated to give 5,6-dichloropyridine-3-carboxylic acid (800 mg, 91% yield) as a white solid.LCMS (ESI) m/z: 192.0 [M + H]+.

References

[1] Patent: US2013/317000, 2013, A1. Location in patent: Paragraph 0368-0369

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