4-Aminopyridine-2-carboxylic acid Chemical Properties

Melting point:

265 °C

Boiling point:

446.3±30.0 °C(Predicted)

Density 

1.417±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Acetone, Ethanol, Methanol

form 

Solid

pka

1.37±0.50(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C6H6N2O2/c7-4-1-2-8-5(3-4)6(9)10/h1-3H,(H2,7,8)(H,9,10)

InChIKey

JRZBTJVSAANBEV-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=NC=CC(N)=C1

CAS DataBase Reference

100047-36-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

50A-24/25-36/37/39

RIDADR 

2761

Hazard Note 

Irritant

HS Code 

29333990

4-Aminopyridine-2-carboxylic acid Usage And Synthesis

Description

4-Aminopyridine-2-carboxylic acid is an organic synthetic reagent used in the preparation of 4-amino-6-(heterocyclic)pyridine carboxylic acid esters, 4-amino-2,6-dimethylnicotinic acid esters and amides.

Chemical Properties

White solid

Uses

4-Aminopyridine-2-carboxylic acid can be a useful synthetic intermediate

Synthesis

General procedure for the synthesis of 4-aminopyridine-2-carboxylic acid from 4-amino-3,5,6-trichloropyridine-2-carboxylic acid: a thick suspension formed by Picloram (8 g, 33 mmol) and 10% Pd/C (1.2 g) in a 10% aqueous LiOH solution (44 mL) was purged twice with hydrogen, and then under a hydrogen atmosphere (45 PSI) at 40°C for 4 hours with stirring. Subsequently, the mixture was heated to 70°C and maintained for 12 hours. Upon completion of the reaction, the cooled suspension was filtered through diatomaceous earth. The filtrate was acidified to pH=3 in concentrated HCl (~3.5 mL), at which point a precipitate was generated. The solid product was collected by filtration and dried overnight under high vacuum to give the final 4-aminopyridine-2-carboxylic acid as a beige solid (4.6 g, 99% yield).LCMS analysis showed m/z 139.1 (M + H)+ with a retention time of 0.21 minutes.

References

[1] Patent: WO2012/3576, 2012, A1. Location in patent: Page/Page column 96

4-Aminopyridine-2-carboxylic acid(100047-36-7)Related Product Information

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• 4-Aminopyridine
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• Anthranilic acid
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• PICLORAM METHYL ESTER
• Picloram
• Methyl 4-aminopyridine-2-carboxylate
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• 3-AMINOPYRIDINE-4-CARBOXYLIC ACID ETHYL ESTER
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