2-Chloro-5-nitronicotinic acid Chemical Properties

Melting point:

140-143℃

Boiling point:

384.8±42.0 °C(Predicted)

Density 

1.702±0.06 g/cm3(Predicted)

storage temp. 

Store at room temperature

form 

Solid

pka

1.57±0.10(Predicted)

color 

White to yellow

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C6H3ClN2O4/c7-5-4(6(10)11)1-3(2-8-5)9(12)13/h1-2H,(H,10,11)

InChIKey

WOFZRBCITDVRON-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C([N+]([O-])=O)C=C1C(O)=O

CAS DataBase Reference

42959-38-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933399990

2-Chloro-5-nitronicotinic acid Usage And Synthesis

Application

2-Chloro-5-nitronicotinic acid is a chemical intermediate used in the synthesis of pesticides and pharmaceuticals. For example, Rhône-Poulenc Agribusiness in France uses it to synthesize novel herbicides.

Synthesis

2-Hydroxy-5-nitro-nicotinic acid (2.7 mmol) in a mixture of NJV- dimethylformamide (2.7 mmol) and thionyl chloride (5 ml) was heated at 80 0C for 1 h. The mixture was allowed to cool and concentrated in a vacuum. To the resulting residue, ice water (20 ml) was added, and with vigorous stirring, a precipitate formed. The precipitate was filtered off and dried in a vacuum oven to give a white solid 2-Chloro-5-nitronicotinic acid (68 percent).

References

[1] Journal of Medicinal Chemistry, 1992, vol. 35, # 10, p. 1887 - 1897
[2] Beilstein Journal of Organic Chemistry, 2009, vol. 5,
[3] Patent: EP904262, 2004, B1. Location in patent: Page 244
[4] Patent: WO2008/46135, 2008, A1. Location in patent: Page/Page column 42-43
[5] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1151 - 1154

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