4,6-Dichloronicotinic acid Chemical Properties

Melting point:

158-160

Boiling point:

337.0±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

1.87±0.25(Predicted)

form 

Solid

color 

White to Light yellow

Water Solubility 

Slightly soluble in water.

Stability:

Hygroscopic

InChI

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

InChIKey

ILMIEWNDXAKVNI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

73027-79-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-20/21/22

Safety Statements 

24/25-36/37

HazardClass 

IRRITANT

HS Code 

29333990

4,6-Dichloronicotinic acid Usage And Synthesis

Chemical Properties

White solid

Uses

4,6-Dichloronicotinic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields.

Synthesis

General procedure for the synthesis of 4,6-dichloronicotinic acid from ethyl 4,6-dichloronicotinate: to a stirred solution of ethyl 4,6-dichloronicotinate (22) (25.95 g, 118 mmol) dissolved in 4:1:1 THF:MeOH:water (600 mL) was added sodium hydroxide solution (40 mL, 6.25 M). After 30 min of reaction, the reaction mixture was acidified to pH 2 with concentrated hydrochloric acid and subsequently diluted with 1:1 EtOAc:Et2O and washed sequentially with water and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting off-white solid was purified by concentrating twice from toluene to give the final target product 4,6-dichloronicotinic acid (23) as a white solid (21.73 g, 96% yield).

References

[1] Patent: US2005/49419, 2005, A1. Location in patent: Page/Page column 24
[2] Patent: US2005/54701, 2005, A1
[3] Tetrahedron Letters, 2011, vol. 52, # 4, p. 512 - 514
[4] Patent: WO2014/52365, 2014, A1. Location in patent: Page/Page column 229-230
[5] Patent: US2015/191464, 2015, A1. Location in patent: Paragraph 0611

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