Chemical Structure and Key Properties

2-(Pyridin-4-yl)benzo[d]oxazol-5-amine (Aladdin SKU: B698893) consists of a benzoxazole bicyclic framework in which the oxygen and nitrogen atoms of the oxazole ring contribute to the compound's planarity and aromatic stability. A 4-pyridyl group is appended at the C-2 position of the oxazole ring, providing an additional nitrogen lone pair available for hydrogen bonding, metal coordination, or ionic interactions. The primary amine at C-5 of the benzene ring further extends the compound's reactivity, enabling acylation, sulfonylation, reductive amination, and condensation reactions.

The extended conjugated system formed by the pyridine–benzoxazole axis is responsible for the compound's predicted UV absorption in the near-UV region and its potential intrinsic fluorescence, properties exploited in optical probe design. The molecule is expected to be a solid at room temperature with moderate polarity, showing limited solubility in water but good solubility in polar aprotic solvents such as DMSO, DMF, and acetonitrile.

Synthesis and Functionalization Strategies

Benzoxazoles bearing a 2-aryl substituent are classically prepared by condensation of 2-aminophenol derivatives with aromatic aldehydes or carboxylic acid equivalents under oxidative conditions, or by cyclocondensation with acid chlorides or nitriles. For 2-(pyridin-4-yl)benzo[d]oxazol-5-amine specifically, a straightforward retrosynthetic disconnection reveals two building blocks: 4-pyridinecarboxaldehyde (or isonicotinoyl chloride) and 2-amino-4-aminophenol (or its protected analogue). The C-5 amine may be introduced either through direct use of a diaminophenol precursor or via post-cyclization reduction of a nitro group.

Once isolated, the free amine at C-5 is a versatile handle for further diversification. Common transformations include: (1) amide bond formation with activated carboxylic acids for library synthesis; (2) reductive amination with aldehydes to yield secondary amines; (3) diazotization followed by coupling reactions to install diverse aryl substituents; and (4) Schiff base formation with carbonyl compounds to generate imine-based ligands for coordination chemistry. The pyridine nitrogen is simultaneously available for N-alkylation or as a directing group in transition-metal-catalyzed C–H functionalization.

Research Applications

Medicinal Chemistry and Drug Discovery: The benzoxazole scaffold is present in several bioactive molecules and approved pharmaceuticals, and its derivatives have been reported to exhibit a range of biological activities including antimicrobial, anticancer, anti-inflammatory, and kinase-inhibitory properties. The combination of a pyridyl group and a free amine in 2-(pyridin-4-yl)benzo[d]oxazol-5-amine provides multiple pharmacophoric features and hydrogen-bond donor/acceptor capacity, making it an attractive lead fragment or building block for structure–activity relationship (SAR) studies.

Coordination and Supramolecular Chemistry: The compound's three nitrogen atoms (benzoxazole N, pyridine N, and amine N) create a rich coordination environment. It can act as a chelating or bridging ligand toward transition metals such as Cu(II), Zn(II), Pd(II), and Pt(II), enabling the construction of metal–organic frameworks (MOFs), coordination polymers, and discrete metallocycles with potential catalytic or luminescent properties.

Fluorescent Probe Development: The extended π-conjugation of the pyridyl-benzoxazole core and the electron-donating amine group create a donor–acceptor push–pull system suitable for designing fluorescent sensors for metal ions, reactive oxygen species (ROS), or biologically relevant analytes. Such probes can be fine-tuned by chemical modification of the amine or pyridine moiety.

Handling, Storage, and Safety Guidelines

Personal Protective Equipment (PPE): When handling 2-(Pyridin-4-yl)benzo[d]oxazol-5-amine, wear appropriate laboratory PPE including nitrile gloves, safety goggles, and a lab coat. Work in a well-ventilated fume hood to minimize inhalation of dust or aerosols. Aromatic amines as a chemical class warrant careful handling; avoid skin contact, inhalation, and ingestion.

Storage: Store the compound in a tightly sealed container in a cool, dry, well-ventilated area, protected from light and moisture. Maintaining low-humidity conditions helps prevent hydrolytic degradation of the oxazole ring or oxidation of the amine functionality. Refrigerated storage (2–8 °C) is advisable for long-term preservation of stock material.

Solvent Recommendations: For stock solution preparation, DMSO is the preferred solvent due to the compound's moderate polarity and good DMSO compatibility. DMF and acetonitrile are suitable alternatives. Aqueous buffers alone are generally not recommended without a co-solvent; if aqueous solutions are required, prepare fresh dilutions from a DMSO stock immediately before use.

Waste Disposal: Dispose of residues and solutions in accordance with local institutional and regulatory guidelines for aromatic amine-containing chemical waste. Do not pour down the drain without treatment.

Quality Specifications and Ordering Information

Aladdin Scientific supplies 2-(Pyridin-4-yl)benzo[d]oxazol-5-amine under SKU B698893. Researchers should consult the product page or contact technical support to obtain the current certificate of analysis (CoA), which specifies purity (typically assessed by HPLC and/or NMR), appearance, and lot-specific analytical data.

When evaluating purity specifications for sensitive assays—such as enzymatic inhibition studies, crystallographic work, or fluorescence measurements—request a CoA and confirm that the reported purity meets the requirements of your application. For high-throughput screening campaigns, consistency of purity across multiple lots is important; Aladdin's quality control procedures are designed to ensure lot-to-lot reproducibility.

To order, visit the Aladdin Scientific website, search by SKU B698893, and select the appropriate pack size. For bulk quantities or custom specifications, contact the Aladdin sales team directly. Standard shipping conditions should maintain compound integrity; upon receipt, inspect the package and store immediately under recommended conditions.