2-Aminonicotinic acid
[CAS# 5345-47-1]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other amino acid derivatives
• Name: 2-Aminonicotinic acid
• Synonyms: 2-Aminopyridine-3-carboxylic acid
• Molecular Formula: C₆H₆N₂O₂
• Molecular Weight: 138.12
• CAS Registry Number: 5345-47-1
• EC Number: 226-296-3
• SMILES: C1=CC(=C(N=C1)N)C(=O)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 295-297 °C (decomp.) (Expl.)
• Index of Refraction: 1.649, Calc.^*
• Boiling Point: 342.3±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 160.8±23.7 °C, Calc.^*
• Water solubility: soluble

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Aminonicotinic acid, also known as 2-aminopyridine-3-carboxylic acid, is a chemical compound with significant applications in organic synthesis and pharmaceutical research. This compound belongs to the family of aminopyridines and is an important intermediate in the synthesis of various bioactive molecules.

The discovery of 2-aminonicotinic acid can be traced back to its recognition as a derivative of nicotinic acid, a naturally occurring compound that plays a vital role in human metabolism, particularly as a precursor to the coenzyme nicotinamide adenine dinucleotide (NAD+). The presence of an amino group at the 2-position of the pyridine ring distinguishes 2-aminonicotinic acid from its parent compound, nicotinic acid, and opens up its potential for further chemical modification and application in various fields.

One of the primary applications of 2-aminonicotinic acid is in the field of medicinal chemistry, where it serves as a building block for the synthesis of various pharmaceutical agents. Its structure is important in the design of compounds that can interact with biological targets, particularly those involved in processes like cell signaling and enzyme inhibition. The amino group in 2-aminonicotinic acid allows for the formation of various derivatives, which can be optimized for specific biological activities.

In addition to its use as a synthetic intermediate, 2-aminonicotinic acid has been investigated for its potential pharmacological activities. Some studies have shown that it may have antimicrobial properties, and it has been explored as a potential candidate for the development of new antimicrobial agents. However, further research is needed to establish the full range of its therapeutic potential.

2-Aminonicotinic acid is also used in the synthesis of heterocyclic compounds, which are of interest due to their wide range of biological activities. These include potential applications in treating diseases such as cancer, diabetes, and neurological disorders. Its ability to participate in various chemical reactions, such as nucleophilic substitution and cyclization, makes it a versatile intermediate in the synthesis of such compounds.

Furthermore, 2-aminonicotinic acid has been used in the development of chelating agents and coordination compounds, particularly those involving transition metals. These metal-complexes are studied for their potential applications in areas like catalysis, materials science, and environmental chemistry.

Overall, 2-aminonicotinic acid plays an important role in organic synthesis and medicinal chemistry, acting as a versatile intermediate in the development of new pharmaceuticals and bioactive compounds. Its discovery and application have contributed to advancements in drug design and the development of new therapeutic agents, particularly in the fields of antimicrobial and anticancer research.

References

2020. Efficient Synthesis of Pyrido[2,3-d]pyrimidines by Recyclization of N-Arylitaconimides with Aminopyrimidinones. Russian Journal of Organic Chemistry, 56(9).
DOI: 10.1134/s107042802009002x

2016. In-Water Synthesis of Quinazolinones from 1,1-Dichloro-2-nitroethene and Anthranilamides. Synlett, 27(12).
DOI: 10.1055/s-0035-1561640

2011. Substituted 2-aminonicotinamides in the synthesis of pyrido[2,3-d]pyrimidin-4(1H)-ones, 2,3-dihydropyrido- [2,3-d]pyrimidin-4(1H)-ones, and 11b,12-dihydropyrido- [2',3':4,5]pyrimido[2,1-a]isoindole-5,7-diones. Chemistry of Heterocyclic Compounds, 47(3).
DOI: 10.1007/s10593-011-0756-6