6-Aminonicotinic acid Chemical Properties

Melting point:

>300 °C (lit.)

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

2.86±0.10(Predicted)

form 

Powder

color 

White to beige

Water Solubility 

ca 1.0 g/L (20 ºC)

Merck 

14,456

BRN 

115992

InChI

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

InChIKey

ZCIFWRHIEBXBOY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

3167-49-5(CAS DataBase Reference)

NIST Chemistry Reference

Nicotinic acid, 6-amino-(3167-49-5)

EPA Substance Registry System

3-Pyridinecarboxylic acid, 6-amino- (3167-49-5)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-23/24/25

Safety Statements 

22-24/25-45-36/37/39-26

WGK Germany 

3

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:6-Aminopyridine-3-carboxylic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

6-Aminonicotinic acid Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

6-Aminopyridine-3-carboxylic acid (6-Aminonicotinic acid) was used in the preparation of resin-bound 2-aminoazine.

Uses

Antiproliferative

Application

6-Aminonicotinic acid is an inhibitor of bacterial DNA gyrase and topoisomerase IV. It has been shown to inhibit the growth of a number of bacteria, including E. coli K-12, with potent inhibitory activity against these enzymes. It binds to the active sites on these enzymes and prevents them from working. The detection time for 6-aminonicotinic acid is about 3 hours after exposure. It has been shown to be more potent than other inhibitors of bacterial DNA gyrase and topoisomerase IV such as 2,4-diaminopyrimidine (2,4DAP).

Definition

ChEBI: An aminonicotinic acid in which the amino group is situated at position 6 of the pyridine ring.

General Description

Electrosynthesis of 6-aminopyridine-3-carboxylic acid (6-aminonicotinic acid) by electrochemical reduction of 2-amino-5-bromo and 2-amino-5-chloropyridine in the presence of CO₂ at silver electrode has been reported.

Purification Methods

Crystallise the acid from aqueous acetic acid. Dry it in vacuo at 70o. [Beilstein 22 III/IV 6726.]

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