2,6-Dichloronicotinic acid ethyl ester Chemical Properties

Melting point:

50.0 to 54.0 °C

Boiling point:

286.0±35.0 °C(Predicted)

Density 

1.367±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

-4.48±0.10(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C8H7Cl2NO2/c1-2-13-8(12)5-3-4-6(9)11-7(5)10/h3-4H,2H2,1H3

InChIKey

KKYBVLDQTWQETN-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933399990

2,6-Dichloronicotinic acid ethyl ester Usage And Synthesis

Synthesis

General procedure: 2,6-dichloronicotinic acid (25.5 g, 0.1328 mol) was mixed with ethanol (200 mL) under nitrogen protection and 96% sulfuric acid (1.7 g) was added as catalyst. The reaction mixture was heated to reflux temperature for esterification. Upon completion of the reaction, ethyl 2,6-dichloronicotinate was obtained as a gray solid (24.89 g, 0.1131 mol, 85.2% yield) after conventional post-treatment. The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 8.30 (d, J = 8.1 Hz, 1H), 7.71 (d, J = 8.1 Hz, 1H), 4.33 (q, J = 7.2 Hz, 2H) and 1.30 (t, J = 7.2 Hz, 3H) ppm.

References

[1] Patent: US2015/291629, 2015, A1. Location in patent: Paragraph 0722-0723
[2] Patent: WO2009/150230, 2009, A1. Location in patent: Page/Page column 134
[3] Patent: WO2010/116282, 2010, A1. Location in patent: Page/Page column 65
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4273 - 4288
[5] Patent: US2006/194801, 2006, A1. Location in patent: Page/Page column 38-39

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