7-Bromo-2-methylbenzo[d]oxazole: Properties, Handling & Applications

7-Bromo-2-methylbenzo[d]oxazole is a brominated benzoxazole heterocyclic compound widely used as a versatile synthetic building block in medicinal chemistry, cross-coupling reactions, and the preparation of biologically active molecules.

Chemical Name

7-Bromo-2-methylbenzo[d]oxazole

Molecular Formula

C₈H₆BrNO

Molecular Weight

212.04 g/mol

Core Scaffold

Benzo[d]oxazole (fused bicyclic: benzene + oxazole)

Key Functional Handles

C–Br (position 7) for cross-coupling; C–CH₃ (position 2) for further functionalization

Aladdin SKU

B733201

Recommended Storage

Cool, dry, well-ventilated area; away from light and moisture

Chemical Identity and Physical Properties

7-Bromo-2-methylbenzo[d]oxazole (SKU B733201) belongs to the benzoxazole family of aromatic heterocycles, featuring a bicyclic system formed by the fusion of a benzene ring with a 1,3-oxazole ring. The compound carries two strategically positioned substituents: a bromine atom at the 7-position of the benzo-fused ring and a methyl group at the 2-position of the oxazole ring.

The molecular formula is C₈H₆BrNO with a molecular weight of approximately 212.04 g/mol. The presence of the electron-withdrawing nitrogen and oxygen atoms within the ring system imparts significant aromatic stability, while the C-7 bromine serves as an excellent handle for metal-catalyzed cross-coupling reactions. The 2-methyl group can undergo benzylic functionalization (e.g., oxidation, halogenation) to further diversify the chemical space accessible from this scaffold.

Note: Specific physical constants (melting point, boiling point, density, solubility) should be confirmed against the current Aladdin Certificate of Analysis for lot-specific data.

Synthetic Applications and Reactivity

The C–Br bond at the 7-position makes 7-Bromo-2-methylbenzo[d]oxazole a highly reactive partner in a variety of palladium- and copper-catalyzed cross-coupling reactions, including:

• Suzuki–Miyaura coupling: Reaction with aryl- or heteroarylboronic acids to construct biaryl and heteroaryl frameworks.
• Buchwald–Hartwig amination: Introduction of nitrogen nucleophiles to generate aminobenzoxazole derivatives relevant to pharmaceutical research.
• Negishi and Kumada couplings: Use of organozinc or organomagnesium reagents to install carbon substituents at C-7.
• C–H activation strategies: The electron-deficient heterocyclic ring can direct ortho-metalation or serve as a directing group in transition-metal-catalyzed C–H functionalization.

The 2-methyl group offers an additional site for elaboration. Benzylic bromination (e.g., NBS/radical conditions) affords the 2-(bromomethyl) derivative, which can be used in nucleophilic substitutions, Wittig-type reactions, or as an electrophilic alkylating agent. Sequential functionalization of both sites enables rapid construction of structurally complex benzoxazole-containing scaffolds.

Safe Handling, Storage, and Disposal

As with all organobromine heterocyclic reagents, appropriate laboratory safety practices must be followed when handling 7-Bromo-2-methylbenzo[d]oxazole.

Personal Protective Equipment (PPE): Wear chemical-resistant gloves (nitrile recommended), a laboratory coat, and safety goggles. Where dust or aerosol generation is possible, use a fume hood.

Storage: Store in a tightly sealed container in a cool (ideally 2–8 °C or as specified on the product label), dry, and well-ventilated location, protected from light and moisture. Keep away from incompatible materials such as strong oxidizers, strong acids, and strong bases.

Spill Management: Contain spills using inert absorbent material (e.g., vermiculite or dry sand). Collect and place in a labeled waste container. Avoid generating dust.

Disposal: Dispose of in accordance with all applicable local, regional, and national regulations governing organobromine chemical waste. Do not dispose of via drain or general waste.

Important: Always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before use. SDS-specific hazard classifications and first-aid measures take precedence over general guidance.

Role in Medicinal Chemistry and Drug Discovery

The benzoxazole ring system is a privileged scaffold in medicinal chemistry, appearing in numerous bioactive natural products and approved pharmaceuticals. Its planar aromatic system facilitates intercalation and π-stacking interactions with biological macromolecules, while the ring nitrogen and oxygen contribute to hydrogen-bond-acceptor capacity.

7-Bromo-2-methylbenzo[d]oxazole is particularly valued because it simultaneously offers two orthogonal handles for diversification: the halogen at C-7 for cross-coupling-based library synthesis, and the methyl group at C-2 for further transformation. This bifunctionality makes it efficient for generating arrays of analogs in structure–activity relationship (SAR) studies targeting kinases, GPCRs, ion channels, antimicrobial targets, and anti-inflammatory pathways.

Researchers in fragment-based drug discovery (FBDD) also utilize compact brominated benzoxazole fragments as starting points for fragment elaboration and fragment-linking strategies.

Note: Specific biological activity data for this compound should be sourced from peer-reviewed literature. No direct pharmacological claims are made here.

Quality, Purity, and Procurement from Aladdin Scientific

Aladdin Scientific supplies 7-Bromo-2-methylbenzo[d]oxazole under SKU B733201. Each lot is accompanied by a Certificate of Analysis (CoA) specifying purity (typically assessed by GC or HPLC), appearance, and lot-specific analytical data.

When placing an order, researchers should:

• Confirm the required quantity and available pack sizes with the Aladdin sales or technical team.
• Request the current CoA and SDS prior to or at the time of shipment.
• Verify compatibility with your downstream application—for highly sensitive cross-coupling reactions, reagent-grade purity (≥97% or higher) is recommended.

For bulk quantities, custom synthesis inquiries, or technical questions regarding application suitability, contact Aladdin Scientific's technical support team directly.

Frequently asked questions

What cross-coupling reactions is 7-Bromo-2-methylbenzo[d]oxazole suitable for?

The C–Br bond at the 7-position is compatible with Suzuki–Miyaura, Buchwald–Hartwig, Negishi, and Kumada coupling protocols, as well as C–H activation strategies. Standard palladium or copper catalysts used for aryl bromides are generally applicable, though optimization of conditions is recommended for each specific transformation.

How should 7-Bromo-2-methylbenzo[d]oxazole be stored to maintain stability?

Store the compound in a tightly sealed container under cool, dry, and dark conditions. Refrigerated storage (2–8 °C) is generally recommended for long-term stability. Protect from moisture and strong oxidizing agents. Always refer to the Aladdin-supplied SDS and CoA for lot-specific storage recommendations.

Can the 2-methyl group of this compound be further functionalized?

Yes. The 2-methyl group can undergo benzylic halogenation (e.g., using NBS under radical initiation) to yield the 2-(bromomethyl)benzo[d]oxazole analog, which is a useful electrophile for further derivatization. Oxidation under appropriate conditions can also convert the methyl to an aldehyde or carboxylic acid, expanding the synthetic utility of this scaffold.

What is the purity of Aladdin's B733201, and how is it tested?

Purity and analytical methodology are specified on the Certificate of Analysis (CoA) issued for each individual lot. Typical methods for benzoxazole derivatives include GC or HPLC purity assessment. Please request the current lot CoA from Aladdin Scientific at the time of ordering to obtain exact purity figures.

Is 7-Bromo-2-methylbenzo[d]oxazole suitable for use in fragment-based drug discovery?

Yes. The compact bicyclic benzoxazole core with low molecular weight and two orthogonal functionalization handles makes this compound an attractive fragment for FBDD programs. It can serve as a fragment starting point for elaboration toward higher-affinity leads via cross-coupling or benzylic functionalization.

References

1. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General reference for benzoxazole chemistry)
2. Negishi, E. (Ed.) Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002. (Reference for Pd-catalyzed cross-coupling with aryl bromides)
3. Narasimhan, B.; Sharma, D.; Kumar, P. Biological importance of the indole nucleus in recent years: A comprehensive review. J. Pharm. Pharmacol. 2011, 63, 1165–1173. (Cited as analogous privileged scaffold review; benzoxazole-specific review reference needs verification)
4. Aladdin Scientific Certificate of Analysis, SKU B733201, 7-Bromo-2-methylbenzo[d]oxazole. (Lot-specific analytical data; request from supplier)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.