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5-Aminonicotinic acid

Product Name5-Aminonicotinic acid
CAS24242-19-1
MFC6H6N2O2
MW138.12
EINECS625-282-8
MOL File24242-19-1.mol

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
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English

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.

Application

5-aminonicotinic acid is an aminonicotinic acid, it is mainly used as a biochemical reagent and pharmaceutical chemical intermediate.

Hazard

5-Aminonicotinic acid has acute oral toxicity and acute dermal toxicity, it causes skin irritation and serious eye irritation.

Synthesis

20826-04-4

24242-19-1

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

5-Aminonicotinic acid

Chemical Properties

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MSDS

Usage And Synthesis

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