What Is 2-Pyridin-3-yl-benzooxazol-5-ylamine?

2-Pyridin-3-yl-benzooxazol-5-ylamine (Aladdin SKU B698892) is a bifunctional heterocyclic compound featuring a benzoxazole bicyclic core. The benzoxazole ring is an oxygen- and nitrogen-containing fused aromatic system known for its planar geometry, chemical stability, and intrinsic fluorescence. At the 2-position of the benzoxazole, a 3-pyridinyl (nicotinic-type) group is attached, introducing an additional basic nitrogen that enables coordination chemistry and hydrogen-bonding interactions. The free primary amine at the 5-position of the benzoxazole ring provides a highly reactive handle for further chemical elaboration, including acylation, sulfonylation, reductive amination, and coupling reactions. This combination of features makes the compound a compact yet functionally rich building block used across multiple areas of chemical biology and drug discovery.

Handling, Storage, and Safety Considerations

As with most aromatic amines, 2-Pyridin-3-yl-benzooxazol-5-ylamine should be handled with standard laboratory precautions. Personnel should wear appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a lab coat. Work should be performed in a well-ventilated area or fume hood when weighing or dissolving the compound, as fine powders can present inhalation risks.

For storage, the compound should be kept in a tightly sealed container away from moisture, heat, and direct light. A cool, dry environment such as a refrigerator (2–8 °C) or freezer (−20 °C) is generally recommended for long-term stability of aromatic amine compounds, as oxidation and photo-degradation can be concerns. Users should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for compound-specific hazard classifications and disposal guidance before use.

Solubility and Solution Preparation

2-Pyridin-3-yl-benzooxazol-5-ylamine contains a planar, aromatic, hydrophobic benzoxazole-pyridine scaffold balanced by the polar primary amine group. As a result, the compound typically shows limited solubility in pure water but can be dissolved in polar aprotic organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), or N-methyl-2-pyrrolidone (NMP). Dilute aqueous solutions may be achievable when the amine is protonated under mildly acidic conditions.

When preparing stock solutions, it is recommended to dissolve the compound in DMSO at an appropriate concentration (commonly 10–100 mM), vortex thoroughly, and sonicate if necessary to achieve complete dissolution. For biological assays requiring aqueous media, the DMSO stock can be diluted to keep the final DMSO concentration below 0.1–0.5% to minimize solvent effects on biological systems. Always prepare fresh dilutions or verify stability of stored solutions before use.

Research Applications

Medicinal Chemistry and Drug Discovery: The benzoxazole scaffold is well-represented in bioactive molecules and approved pharmaceuticals. The free amine at the 5-position of 2-Pyridin-3-yl-benzooxazol-5-ylamine allows rapid derivatization to generate amide, urea, sulfonamide, and carbamate libraries for structure–activity relationship (SAR) studies. The pyridine nitrogen can participate in hydrogen bonding with biological targets.

Fluorescent Probe Development: Benzoxazole derivatives are known for their UV-absorbing and fluorescence-emitting properties. This compound may serve as a core unit for designing sensors or probes targeting metal ions, reactive oxygen species, or biomolecules. The amine group can be conjugated to recognition units or reporting groups.

Coordination Chemistry and Ligand Design: The pyridine nitrogen and the benzoxazole nitrogen provide multiple donor sites, making this compound a candidate chelating or bridging ligand for transition metal complexes used in catalysis or materials science.

Synthetic Intermediate: The primary amine is a versatile handle for introducing the benzoxazolyl-pyridine fragment into more complex molecular architectures via standard organic transformations.

Ordering and Quality Information

2-Pyridin-3-yl-benzooxazol-5-ylamine is available from Aladdin Scientific under catalog number B698892. When placing an order, please reference the SKU to ensure you receive the correct compound. Aladdin Scientific provides reagent-grade compounds supported by quality control documentation including purity data typically determined by HPLC and/or NMR analysis. For specific purity certificates, analytical data, or bulk quantity inquiries, please contact Aladdin Scientific's customer service or your regional representative. Orders can be placed through the Aladdin Scientific website or through authorized distributors. For international orders, please consult current shipping regulations regarding the transport of chemical compounds in your jurisdiction.