2-Amino-3-pyridinecarboxaldehyde
[CAS 7521-41-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 2-Amino-3-pyridinecarboxaldehyde
• Synonyms: 2-Amino-3-formylpyridine; 2-Aminonicotinaldehyde
• Molecular Formula: C₆H₆N₂O
• Molecular Weight: 122.12
• CAS Registry Number: 7521-41-7
• EC Number: 626-730-5
• SMILES: C1=CC(=C(N=C1)N)C=O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 98-102 °C (Expl.)
• Index of Refraction: 1.652, Calc.^*
• Boiling Point: 290.7±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 129.6±23.2 °C, Calc.^*
• Water solubility: insoluble

^* 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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Amino-3-pyridinecarboxaldehyde is an organic chemical compound that contains both an amino group and an aldehyde functional group attached to a pyridine ring. This compound has garnered interest due to its utility in various synthetic applications, particularly in the preparation of biologically active molecules and in the development of pharmaceutical intermediates.

The discovery of 2-amino-3-pyridinecarboxaldehyde is linked to ongoing research in the field of pyridine chemistry, which has a long history due to the diverse applications of pyridine derivatives. Pyridine itself is an important heterocyclic compound, known for its ability to participate in a variety of chemical reactions, and modifications to the pyridine ring structure have resulted in numerous derivatives with distinct reactivity and biological properties. The addition of the amino and aldehyde groups to the pyridine ring further expands the chemical reactivity and potential uses of this compound.

2-Amino-3-pyridinecarboxaldehyde is primarily used in the synthesis of complex organic compounds. One of its most important applications is in the preparation of pharmaceutical intermediates. The compound serves as a building block for the synthesis of molecules with potential therapeutic activities, including those with antimicrobial, antiviral, and anticancer properties. The presence of both the amino and aldehyde functional groups makes 2-amino-3-pyridinecarboxaldehyde a valuable intermediate for coupling reactions and the formation of more complex molecular structures.

In addition to its use in medicinal chemistry, 2-amino-3-pyridinecarboxaldehyde also plays a role in the synthesis of agrochemicals, where its ability to undergo various chemical reactions is exploited. The compound's structure, with its pyridine ring and functional groups, allows it to be used in the development of new pesticides, herbicides, and fungicides. These applications benefit from the compound’s bioactivity and its potential to interact with biological systems in specific ways.

2-Amino-3-pyridinecarboxaldehyde has also been explored in materials science for its potential use in the preparation of novel organic materials and coordination compounds. The reactivity of the amino and aldehyde groups makes it suitable for the synthesis of chelating agents, which are of interest in fields such as catalysis and environmental remediation.

Research continues into the full scope of applications for 2-amino-3-pyridinecarboxaldehyde, as its reactivity and functional versatility continue to be valuable in organic synthesis. Its role in drug discovery, agrochemical development, and materials science positions it as an important compound in various fields of chemical research and industrial applications.

In summary, 2-amino-3-pyridinecarboxaldehyde is a versatile organic compound with significant applications in organic synthesis, particularly as a building block for the development of biologically active molecules. Its utility in medicinal chemistry, agrochemicals, and materials science highlights its importance as a synthetic intermediate in the production of novel compounds. The chemical properties of 2-amino-3-pyridinecarboxaldehyde continue to be leveraged in the pursuit of new therapeutic agents, agricultural products, and materials for various industrial uses.

References

2023. Green pathway for the construction of aryl-1,8-naphthyridine-thiazole scaffolds and in vitro-antimicrobial evaluation, DNA binding interactions, viscosity measurements, molecular modeling studies and ADME properties. Research on Chemical Intermediates, 50(2).
DOI: 10.1007/s11164-023-05176-3

2021. Structural elucidation, theoretical investigation, biological screening and molecular docking studies of metal(II) complexes of NN donor ligand derived from 4-(2-aminopyridin-3-methylene)aminobenzoic acid. Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine, 34(3).
DOI: 10.1007/s10534-021-00293-1

2019. Crystal Structure of Mono- and Trinuclear Ni(II) Complexes with Bis-Azomethine Based on 2-Amino-3-Formylpyridine. Russian Journal of Coordination Chemistry, 45(3).
DOI: 10.1134/s107032841902009x