5-Aminonicotinic acid Chemical Properties

Melting point:

293 °C

Boiling point:

253.51°C (rough estimate)

Density 

1.3471 (rough estimate)

refractive index 

1.5100 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2.36±0.10(Predicted)

form 

Crystalline Powder

color 

Golden-brown

BRN 

115848

InChI

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

InChIKey

BYIORJAACCWFPU-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

24242-19-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

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

Safety Statements 

36/37/39-26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

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5-Aminonicotinic acid Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

5-Aminonicotinic acid is used in the synthesis of coordination polymers, bioluminescent reagents and biological active agents.

Definition

ChEBI: 5-aminonicotinic acid is an aminonicotinic acid in which the amino group is situated at position 5 of the pyridine ring. It has a role as a metabolite. It is an aromatic amine, an aminopyridine and an aminonicotinic acid. It is functionally related to a nicotinic acid.

Synthesis

The general procedure for the synthesis of 5-aminonicotinic acid from 5-bromonicotinic acid was as follows: 5-bromo-3-pyridinecarboxylic acid (25 g, 0.124 mol) was mixed with ammonia (67.32 mL) and copper sulfate pentahydrate (8.41 g) was added. The reaction mixture was transferred to an autoclave, heated to 120 °C and kept for 16 hours. The reaction process was monitored by thin layer chromatography (TLC) using ninhydrin as a color developer. Upon completion of the reaction, the reaction mixture was washed with saturated sodium sulfide solution to remove copper ions, followed by adjusting the pH to 4-5 with concentrated hydrochloric acid.The acidified mixture was cooled to precipitate solids. The solid product was collected by filtration and dried to give 5-aminonicotinic acid (12.9 g, 74% yield).

References

[1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6340 - 6350
[2] Patent: WO2004/35545, 2004, A2. Location in patent: Page 46
[3] Patent: WO2003/101959, 2003, A1. Location in patent: Page 50-51
[4] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1981, vol. 35, # 4, p. 289 - 294
[5] Journal of the American Chemical Society, 1948, vol. 70, p. 2381,2383

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