5-(1H-Imidazol-1-yl)pyridin-2-amine: Properties & Research Uses
5-(1H-Imidazol-1-yl)pyridin-2-amine: Properties & Research Uses
5-(1H-Imidazol-1-yl)pyridin-2-amine is a bifunctional nitrogen-rich heterocyclic compound featuring both an imidazolyl substituent and a primary amine group on a pyridine scaffold, making it a versatile building block for medicinal chemistry and materials research.
- IUPAC Name
- 5-(1H-imidazol-1-yl)pyridin-2-amine
- SKU
- P691135
- Core Scaffold
- 2-aminopyridine with N-linked imidazole at the 5-position
- Key Functional Groups
- Primary amine (–NH₂) and imidazolyl ring (N-heterocycle)
- Relevance in Synthesis
- Bifunctional linker and pharmacophore fragment in drug discovery
- Supplier
- Aladdin Scientific
Chemical Structure and Properties
5-(1H-Imidazol-1-yl)pyridin-2-amine consists of a pyridine ring bearing a primary amino group at the 2-position and an imidazol-1-yl (N-substituted imidazole) moiety at the 5-position. This arrangement produces a planar, aromatic, nitrogen-rich framework with multiple hydrogen-bond donor and acceptor sites.
The primary amine at C-2 of the pyridine acts as both a hydrogen-bond donor and a handle for further functionalization via acylation, reductive amination, or heterocycle formation. The imidazole ring, connected through its N-1 nitrogen to the pyridine C-5, contributes additional basicity and metal-coordination capacity. The combination of these features gives the molecule a calculated polar surface area and LogP profile consistent with drug-like fragments.
The compound is typically a solid at room temperature. Researchers should consult the certificate of analysis (CoA) supplied with each lot (SKU P691135) for confirmed purity, melting point, and spectral data.
Synthesis and Functionalization Strategies
The core structure of 5-(1H-imidazol-1-yl)pyridin-2-amine can be assembled by N-arylation of imidazole onto a 5-halopyridin-2-amine precursor (e.g., 5-bromo- or 5-iodopyridin-2-amine) under copper- or palladium-catalyzed cross-coupling conditions, or via nucleophilic aromatic substitution when the halide is activated by adjacent electron-withdrawing groups.
Once obtained, the compound serves as a versatile synthetic intermediate. The amine group enables coupling to carboxylic acids (amide bond formation), condensation with aldehydes, and cyclization reactions to form fused heterocycles such as benzimidazoles or quinazolines. The imidazole nitrogen(s) can coordinate to transition metals, making the compound useful as a ligand precursor in catalysis and supramolecular chemistry.
Researchers planning multi-step sequences should note that the free amine may require orthogonal protection (e.g., Boc or acetyl) to prevent side reactions during further elaboration of the imidazole or pyridine ring.
Research and Medicinal Chemistry Applications
Compounds combining an aminopyridine with an imidazole pharmacophore appear frequently in medicinal chemistry programs targeting kinases, G-protein-coupled receptors, and ion channels, because the aminopyridine motif is a recognized hinge-binding fragment in many ATP-competitive inhibitors, while imidazole provides additional hydrogen-bonding and metal-chelation interactions with catalytic residues.
5-(1H-Imidazol-1-yl)pyridin-2-amine is therefore valuable as a fragment in fragment-based drug discovery (FBDD) campaigns and as a building block for generating focused libraries via parallel synthesis. Its nitrogen-rich character also makes it attractive in materials science for the preparation of metal-organic frameworks (MOFs) and coordination polymers where bridging N-donor ligands are required.
Additionally, the compound may serve as a starting point for the exploration of antimicrobial and anti-inflammatory agents, given the established biological relevance of both the imidazole and aminopyridine sub-structures in these therapeutic areas.
Handling, Storage, and Safety Considerations
As with all research-grade fine chemicals, 5-(1H-imidazol-1-yl)pyridin-2-amine should be handled in a well-ventilated fume hood with appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a laboratory coat. Avoid inhalation of dust or aerosols.
The compound should be stored in a tightly sealed container, protected from moisture and light, at the temperature specified on the product label or CoA. Many aminopyridine and imidazole derivatives are hygroscopic; exposure to air and humidity can lead to degradation or caking, which may affect purity and reproducibility of experimental results.
Dispose of waste in accordance with local institutional and regulatory guidelines for nitrogen-containing heterocyclic organic compounds. Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for hazard classification, first-aid measures, and disposal procedures specific to this material (SKU P691135).
Frequently asked questions
What is the primary application of 5-(1H-Imidazol-1-yl)pyridin-2-amine in drug discovery?
It is primarily used as a bifunctional building block and pharmacophore fragment in medicinal chemistry, particularly in fragment-based drug discovery programs targeting kinases and other enzymes where aminopyridine motifs engage the hinge region and the imidazole provides supplementary binding interactions.
How should I store 5-(1H-Imidazol-1-yl)pyridin-2-amine to maintain its purity?
Store the compound in a tightly sealed container away from moisture, light, and heat at the conditions specified on the product label or certificate of analysis. Because aminopyridine and imidazole derivatives can be hygroscopic, minimize exposure to ambient air when weighing or transferring the material.
Can 5-(1H-Imidazol-1-yl)pyridin-2-amine be used to prepare metal-organic frameworks (MOFs)?
Yes, the compound's multiple nitrogen donor atoms — from both the imidazole ring and the pyridine/amine groups — make it a candidate ligand precursor for coordination polymers and MOFs. However, specific framework formation conditions and metal compatibility should be established empirically and verified against published literature for structurally analogous systems.
What functional group transformations are possible at the amine of this compound?
The primary amine can undergo acylation to form amides, reductive amination to give secondary or tertiary amines, condensation with carbonyl compounds, diazotization followed by substitution or coupling reactions, and cyclization to fused heterocycles such as quinazolines or benzimidazoles, providing broad synthetic versatility.
References
- Aladdin Scientific product page for 5-(1H-Imidazol-1-yl)pyridin-2-amine, SKU P691135.
- Meanwell, N. A. Improving drug candidates by design: a focus on physicochemical properties as a means of improving compound disposition and safety. Chem. Res. Toxicol. 2011, 24, 1420–1456.
- Hajduk, P. J.; Greer, J. A decade of fragment-based drug design: strategic advances and lessons learned. Nat. Rev. Drug Discov. 2007, 6, 211–219.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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