5-(1H-Imidazol-1-yl)pyridin-2-amine: Properties & Applications
5-(1H-Imidazol-1-yl)pyridin-2-amine: Properties & Applications
5-(1H-Imidazol-1-yl)pyridin-2-amine is a bifunctional heterocyclic compound featuring both an imidazole ring and an aminopyridine moiety, making it a versatile building block for medicinal chemistry, coordination chemistry, and the synthesis of pharmacologically active molecules.
- IUPAC Name
- 5-(1H-imidazol-1-yl)pyridin-2-amine
- Molecular Formula
- C₈H₈N₄
- Molecular Weight
- 160.18 g/mol
- Core Scaffold
- Imidazolyl-aminopyridine bifunctional heterocycle
- Primary Application
- Pharmaceutical intermediate and medicinal chemistry building block
- SKU
- P691135
Chemical Structure and Key Physicochemical Properties
5-(1H-Imidazol-1-yl)pyridin-2-amine (CAS not confirmed in source material; see review flags) consists of a pyridine ring bearing a primary amine group at the 2-position and an N-linked imidazole ring at the 5-position. The molecular formula is C₈H₈N₄, giving a molecular weight of approximately 160.18 g/mol. The compound contains four nitrogen atoms distributed across the two heterocyclic systems: two ring nitrogens in the imidazole, one ring nitrogen in the pyridine, and one exocyclic primary amine nitrogen. This high nitrogen content confers significant hydrogen-bond donor and acceptor capacity, relevant for both solubility and target binding in drug discovery contexts. The imidazole nitrogen atoms can act as metal-coordination sites, while the 2-amino group of the pyridine provides an additional hydrogen-bond donor, collectively making the molecule attractive for diverse molecular recognition applications.
Synthesis Relevance and Role as a Building Block
The compound represents a class of N-aryl imidazole derivatives that are commonly prepared through nucleophilic aromatic substitution (SNAr) or copper-catalyzed C–N coupling reactions between 2-amino-5-halopyridines and imidazole. Its dual functionality — a coordinatively versatile imidazole and a reactive primary amine — enables downstream derivatization via acylation, reductive amination, condensation, or coupling reactions. This versatility positions 5-(1H-imidazol-1-yl)pyridin-2-amine as a privileged scaffold in the preparation of kinase inhibitors, antimicrobial agents, and other bioactive small molecules. Researchers in medicinal chemistry routinely employ such bifunctional heterocyclic amines as linkers or pharmacophore fragments in multi-component reaction strategies.
Applications in Drug Discovery and Coordination Chemistry
In drug discovery, the imidazolyl-aminopyridine motif is recognized for its ability to interact with biological targets through multiple binding modes, including hydrogen bonding via the exocyclic amine, π-stacking through the aromatic rings, and coordination to metal centers in metalloenzymes. Compounds incorporating this scaffold have been investigated as potential leads for anticancer, antimicrobial, and anti-inflammatory applications, though specific biological data for 5-(1H-imidazol-1-yl)pyridin-2-amine itself should be verified through primary literature. In coordination chemistry, the compound's imidazole nitrogen and pyridyl nitrogen can chelate transition metals such as copper, zinc, palladium, and ruthenium, facilitating the design of metal complexes for catalysis and supramolecular chemistry. Its use as a ligand precursor in organometallic synthesis is therefore well-founded from a structural standpoint.
Handling, Storage, and Quality Considerations
As with most heterocyclic amine building blocks, 5-(1H-imidazol-1-yl)pyridin-2-amine should be handled with standard laboratory precautions: use appropriate personal protective equipment including gloves, safety glasses, and a lab coat. Work in a well-ventilated area or fume hood when handling powders to avoid inhalation of fine particulates. The compound should be stored in a cool, dry location away from strong oxidizing agents and direct light to prevent degradation. Specific storage temperature recommendations and confirmed purity specifications for Aladdin Scientific's offering (SKU P691135) should be confirmed via the product datasheet. Users are advised to verify purity by standard analytical methods such as HPLC and NMR before use in sensitive assays or synthetic routes requiring high chemical fidelity.
Frequently asked questions
What is 5-(1H-Imidazol-1-yl)pyridin-2-amine used for in research?
It is primarily used as a bifunctional building block in medicinal chemistry for the synthesis of pharmacologically active compounds, including potential kinase inhibitors and antimicrobial agents. It also serves as a ligand precursor in coordination and organometallic chemistry due to its multiple nitrogen donor sites.
How should 5-(1H-Imidazol-1-yl)pyridin-2-amine be stored to maintain stability?
The compound should be stored in a cool, dry environment, away from strong oxidizing agents and direct light. Consult the Aladdin Scientific product datasheet for confirmed temperature and humidity specifications specific to SKU P691135.
What reactive sites does 5-(1H-Imidazol-1-yl)pyridin-2-amine offer for further chemical derivatization?
The primary amine at the 2-position of the pyridine ring is amenable to acylation, reductive amination, and condensation reactions, while the imidazole ring nitrogen atoms can participate in alkylation and metal coordination. Together, these sites provide multiple handles for the synthesis of more complex molecular architectures.
What analytical methods are recommended for purity verification of this compound?
HPLC (high-performance liquid chromatography) and NMR spectroscopy (¹H and ¹³C) are the standard analytical techniques recommended for confirming purity and structural identity prior to use in sensitive applications. Mass spectrometry can provide additional confirmation of molecular identity.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for nucleophilic aromatic substitution and heterocyclic amine chemistry.
- Katritzky, A. R.; Ramsden, C. A.; Joule, J. A.; Zhdankin, V. V. Handbook of Heterocyclic Chemistry, 3rd ed. Elsevier. General reference for imidazole and pyridine chemistry.
- Aladdin Scientific Product Datasheet, SKU P691135: 5-(1H-Imidazol-1-yl)pyridin-2-amine. Aladdin Scientific, Shanghai.
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