Chemical Structure and Physicochemical Properties

7-Bromobenzo[d]oxazol-2-amine consists of a bicyclic benzo[d]oxazole ring system substituted with an amino group at the C-2 position and a bromine atom at the C-7 position. The molecular formula is C₇H₅BrN₂O, giving a molecular weight of approximately 213.03 g/mol.

The benzo[d]oxazole scaffold is an aromatic, electron-deficient bicyclic system formed by the fusion of a benzene ring with a 1,3-oxazole ring. The 2-amino substituent acts as an electron donor, partially counteracting the ring's electron-withdrawing character, while the 7-bromo substituent introduces a site for further functionalization via transition-metal-catalyzed cross-coupling reactions.

The compound is expected to be a solid at room temperature. Solubility characteristics are typical of halogenated heteroaromatic amines: moderate solubility in polar aprotic solvents such as DMSO and DMF, limited solubility in water, and reasonable solubility in common organic solvents such as ethanol, acetone, and dichloromethane. Researchers should verify exact solubility data from the certificate of analysis supplied with each lot.

Safe Handling and Storage Guidelines

As with all halogenated heteroaromatic amines, 7-Bromobenzo[d]oxazol-2-amine should be handled with appropriate precautions. Users must consult the Safety Data Sheet (SDS) before use.

Personal Protective Equipment (PPE): Wear chemical-resistant gloves (nitrile recommended), a laboratory coat, and eye protection (safety glasses or goggles) when handling this compound. Use in a fume hood to avoid inhalation of dust or vapors.

Storage: Store in a tightly sealed container in a cool (typically 2–8 °C or room temperature as specified on the product label), dry, and well-ventilated area, protected from light and moisture. Segregate from strong oxidizers, strong acids, and strong bases.

Disposal: Dispose of waste in accordance with local, regional, and national regulations governing halogenated organic waste. Do not pour down the drain.

First Aid: In case of skin or eye contact, rinse thoroughly with water for at least 15 minutes and seek medical attention if irritation persists. If inhaled, move to fresh air immediately.

Applications in Medicinal Chemistry and Organic Synthesis

7-Bromobenzo[d]oxazol-2-amine is a bifunctional heterocyclic building block offering two independent handles for chemical elaboration: the 2-aminobenzoxazole moiety and the aryl bromide.

Cross-Coupling Reactions: The C-7 aryl bromide is amenable to palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura (with aryl- or alkenylboronic acids), Buchwald–Hartwig (for C–N bond formation), Sonogashira (with terminal alkynes), and Negishi couplings. These reactions enable rapid diversification of the benzoxazole core for structure–activity relationship (SAR) studies.

Condensation and Amide Bond Formation: The primary amine at C-2 can participate in acylation, sulfonylation, reductive amination, and condensation reactions, providing access to amide, sulfonamide, and imine derivatives with diverse pharmacological profiles.

Drug Discovery: The 2-aminobenzoxazole scaffold is a privileged structure in medicinal chemistry, found in or used to design inhibitors targeting kinases, ion channels, and other therapeutically relevant proteins. The additional bromine handle at C-7 gives synthetic chemists the flexibility to attach diverse pharmacophores or linkers during lead optimization.

Materials Science: Benzoxazole-containing compounds are also of interest in the development of fluorescent probes and functional organic materials, though the primary utility of this specific compound is as a synthetic intermediate.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies 7-Bromobenzo[d]oxazol-2-amine under SKU B734979. Researchers should request the Certificate of Analysis (CoA) for each specific lot to verify purity (typically assessed by HPLC and/or NMR), identity (confirmed by mass spectrometry and/or IR), and any additional quality parameters relevant to their application.

When evaluating reagent quality for sensitive applications such as palladium-catalyzed coupling reactions, high purity (≥95% or greater) is strongly recommended to avoid catalyst poisoning or side reactions that could compromise yield and selectivity.

For bulk quantities, custom packaging, or application-specific quality requirements, contact Aladdin Scientific's technical support team. Procurement teams should reference SKU B734979 in all purchase orders to ensure accurate fulfillment.