Chemical Identity and Structural Features

8-Bromo-2H-benzo[b][1,4]oxazin-3(4H)-one (CAS registry should be confirmed; see review flags) is a bicyclic compound comprising a benzene ring fused to a 1,4-oxazin-3(4H)-one ring. The scaffold contains both an oxygen and a nitrogen heteroatom within the six-membered heterocyclic ring, together with a lactam carbonyl group at the 3-position. The bromine substituent at the 8-position of the aromatic ring is a key handle for downstream functionalization.

The presence of the C–Br bond makes this compound an excellent electrophilic partner in transition-metal-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Negishi couplings. The lactam NH and the ring oxygen provide additional sites for potential hydrogen-bonding interactions, which is relevant when this scaffold is incorporated into biologically active molecules.

Handling, Safety, and Storage Guidelines

As with all halogenated organic compounds, appropriate laboratory safety precautions should be followed when handling 8-Bromo-2H-benzo[b][1,4]oxazin-3(4H)-one. Personnel should wear appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a laboratory coat. Work should be carried out in a well-ventilated fume hood to minimise inhalation exposure to dust or aerosols.

The compound should be stored in a tightly sealed container, away from moisture and direct light, at the temperature recommended on the product certificate of analysis (typically room temperature or 2–8 °C for sensitive intermediates — confirm with CoA). Prolonged or repeated exposure to moisture may affect purity; desiccant storage is advisable. Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

Disposal of waste containing this compound must comply with local and institutional regulations governing halogenated organic waste streams.

Synthetic Applications and Cross-Coupling Utility

The benzoxazinone scaffold is an important pharmacophore and structural motif found in biologically active natural products and drug candidates. The 8-bromo substituent in this compound enables rapid library synthesis through palladium- or nickel-catalyzed cross-coupling reactions, allowing medicinal chemists to install aryl, heteroaryl, vinyl, and amino groups at the 8-position with high selectivity.

Typical transformations include: (1) Suzuki–Miyaura coupling with arylboronic acids to introduce biaryl motifs; (2) Buchwald–Hartwig amination to generate 8-amino derivatives relevant to kinase inhibitor programmes; (3) Sonogashira coupling with terminal alkynes to produce alkynylated benzoxazinone derivatives. The lactam NH can be further alkylated or acylated to tune pharmacokinetic properties of resulting compounds.

Researchers in fragment-based drug discovery (FBDD) may find the compact, rigid benzoxazinone core useful as a fragment hit for elaboration into lead compounds against a range of biological targets.

Quality, Purity, and Procurement

Aladdin Scientific supplies 8-Bromo-2H-benzo[b][1,4]oxazin-3(4H)-one under SKU B730212. Each lot is accompanied by a Certificate of Analysis (CoA) confirming identity, purity, and physical form. Researchers are advised to request the CoA at the time of order or download it from the Aladdin Scientific website using the lot number.

Typical quality checks for this class of compound include: HPLC purity assessment, ¹H and ¹³C NMR confirmation of structure, and high-resolution mass spectrometry (HRMS) for molecular formula verification. The specific purity specification for B730212 should be verified on the current CoA, as specifications may be updated between production lots.

For bulk or custom quantity enquiries, researchers and procurement managers should contact Aladdin Scientific's sales team directly. Volume pricing and custom synthesis options may be available depending on project requirements.