2-Aminonicotinic acid Chemical Properties

Melting point:

295-297 °C (dec.)(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

solubility 

DMSO

pka

2.94±0.10(Predicted)

form 

Crystalline Powder

color 

Off-white to light yellow

Water Solubility 

soluble

BRN 

119031

InChI

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

InChIKey

KPIVDNYJNOPGBE-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5345-47-1(CAS DataBase Reference)

EPA Substance Registry System

2-Aminonicotinic acid (5345-47-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

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

WGK Germany 

3

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

• Language:English Provider:2-Aminopyridine-3-carboxylic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Aminonicotinic acid Usage And Synthesis

Structure

2-aminonicotinic acid (or 2-aminopyridine-3-carboxylic acid, abbreviated ANA) can be a model compound for reactions containing carboxylic and amino groups attached to the pyridine ring. X-ray diffraction studies have shown that in the molecular crystal phase, ANA occurs as a zwitterion in which protonation occurs at the nitrogen atom of the pyridine ring. Infrared spectra of ANA molecular crystal have confirmed that intra- and intermolecular hydrogen bonds are present in its structure. Karabacak et al. investigated the tautomerism of ANA using electronic structure calculations (B3LYP/6-311++G(d,p)) and identified four amino tautomers. Furthermore, Nayak and Dogra optimized the structures of two amino and two imino structures at the B3LYP/6-31G** level. On the basis of both experimental data (absorption and fluorescence spectra) and electronic structure calculations, these authors concluded that ANA is present in solutions as the amino form in both the S0 and S1 states, whereas the imino forms are absent. ANA exists as a molecular species in non-polar and polar aprotic solvents and as a zwitterion in polar protic solvents[1].

Chemical Properties

Off-white to light yellow crystalline powder

Uses

A component of hair dyes.

Uses

2-Aminopyridine-3-carboxylic acid can be used as:

• A ligand to prepare copper(II)-organic coordination compounds.
• A reactant to prepare pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolines by reacting with trimethylsilyl cyanide and phthalaldehyde.
• A reactant to synthesize organo-soluble and thermally stable poly(thiourea-amide-imide) polymers.

Definition

ChEBI: An aminonicotinic acid in which the amino group is situated at position 2 of the pyridine ring.

Synthesis

Step 4. 30 mL of 5 mol-L?1 sodium hydroxide solution was added to a 100 mL flask and cooled to 5 °C. After cooling to 5 °C, 0.02 mol of bromine was added slowly and the reaction was stirred for 0.5 hours. Subsequently, 0.02 mol 2-aminopyridine-3-carboxylic acid was added and the temperature was raised to 85 °C and kept for 2 hours for the reaction. Step 5: After completion of the reaction, the reaction mixture was concentrated under reduced pressure to remove some of the solvent. After cooling, the pH was adjusted to 7 with dilute hydrochloric acid and the precipitate was collected by filtration. The resulting solid was dried and evaporated to give final crystals of 2-aminopyridine-3-carboxylic acid as a white solid.

References

[1] M. Pagacz-Kostrzewa . “Phototransformations of 2-aminonicotinic acid resolved with matrix isolation infrared spectroscopy and ab initio calculations.” Journal of Photochemistry and Photobiology A-chemistry 410 (2021): Article 113187.

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