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2-Aminonicotinic acid

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2-Aminonicotinic acid Basic information
Structure
Product Name:2-Aminonicotinic acid
Synonyms:2-AMino-3-carboxypyridine;Nicotinic acid, 2-aMino- (6CI,7CI,8CI);2-Aminopyridine-3-carboxylic acid, 2-Amino-3-carboxypyridine;NSC 3049;2- aMinoacid;2-AMINO-3-PYRIDINECARBOXYLIC ACID;2-AMINOPYRIDINE-3-CARBOXYLIC ACID;2-AMINONICOTINIC ACID
CAS:5345-47-1
MF:C6H6N2O2
MW:138.12
EINECS:226-296-3
Product Categories:Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;AMINOACID;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Pyridine;Pyridines derivates;Amino Acids and Derivatives;Heterocycles;Amines;blocks;Carboxes;Pyridines;Carboxylic Acids;Aromatics;C6
Mol File:5345-47-1.mol
2-Aminonicotinic acid Structure
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
pka2.94±0.10(Predicted)
form Crystalline Powder
color Off-white to light yellow
Water Solubility soluble
BRN 119031
InChIInChI=1S/C6H6N2O2/c7-5-4(6(9)10)2-1-3-8-5/h1-3H,(H2,7,8)(H,9,10)
InChIKeyKPIVDNYJNOPGBE-UHFFFAOYSA-N
SMILESC1(N)=NC=CC=C1C(O)=O
CAS DataBase Reference5345-47-1(CAS DataBase Reference)
EPA Substance Registry System2-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 TSCA listed
HazardClass IRRITANT
HS Code 29333999
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
2-Aminopyridine-3-carboxylic acid English
SigmaAldrich English
ACROS English
ALFA English
2-Aminonicotinic acid Usage And Synthesis
Structure2-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 PropertiesOff-white to light yellow crystalline powder
UsesA component of hair dyes.
Uses2-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.

DefinitionChEBI: An aminonicotinic acid in which the amino group is situated at position 2 of the pyridine ring.
Synthesis
2-(AMINOCARBONYL)NICOTINIC ACID

5860-70-8

2-Aminonicotinic acid

5345-47-1

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.
Tag:2-Aminonicotinic acid(5345-47-1) Related Product Information
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