Chemical Identity and Structural Features

5-Bromo-6-methyl-1H-benzo[d]imidazole (CAS number requires verification; SKU B681029) belongs to the benzimidazole family of fused bicyclic heterocycles, consisting of a benzene ring annulated to an imidazole ring. The compound carries a bromine atom at position 5 and a methyl group at position 6, creating an asymmetrically substituted aromatic scaffold with molecular formula C₈H₇BrN₂ and a molecular weight of approximately 211.06 g/mol.

The presence of the C-5 bromo substituent is particularly valuable from a synthetic standpoint: it serves as a handle for transition-metal-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Buchwald–Hartwig, and Negishi couplings, enabling straightforward diversification of the aromatic core. The C-6 methyl group introduces steric bias and mild electron-donating character, which can modulate the electronic density of the ring and influence binding interactions in biological targets.

Like all 1H-benzimidazoles, this compound exists in two tautomeric forms due to the mobile NH proton, a feature that must be considered when characterizing samples by NMR spectroscopy or designing structure–activity relationship studies.

Research Applications and Synthetic Utility

Benzimidazole derivatives are among the most clinically validated heterocyclic scaffolds in drug discovery, appearing in proton-pump inhibitors, antiparasitic agents, antifungal drugs, and kinase inhibitors. 5-Bromo-6-methyl-1H-benzo[d]imidazole serves as a privileged building block for the preparation of such pharmacologically active compounds.

Cross-Coupling Chemistry: The C–Br bond undergoes efficient palladium- or nickel-catalyzed coupling reactions with arylboronic acids (Suzuki), organozinc reagents (Negishi), terminal alkynes (Sonogashira), and amines (Buchwald–Hartwig). These transformations allow medicinal chemists to rapidly generate libraries of 5-aryl- or 5-amino-substituted benzimidazoles for biological screening.

N-Alkylation and N-Acylation: The imidazole NH can be selectively alkylated or acylated under mild basic conditions to provide N1-substituted derivatives, useful for probing the role of the NH in target binding and for improving pharmacokinetic properties.

Fragment-Based Drug Discovery (FBDD): The compact, rule-of-five-compliant molecular framework of this compound makes it an attractive fragment for biophysical screening campaigns targeting enzymes, receptors, and protein–protein interactions.

Material Science: Halogenated benzimidazoles have also found use as ligands in coordination chemistry and as components of organic electronic materials, including metal–organic frameworks (MOFs) and luminescent probes.

Handling, Safety, and Storage Guidelines

While 5-Bromo-6-methyl-1H-benzo[d]imidazole is not classified as acutely toxic under standard conditions, good laboratory practice should always be observed when handling any halogenated organic compound. Users should consult the full Safety Data Sheet (SDS) provided with the product before use.

Personal Protective Equipment (PPE): Wear appropriate laboratory coat, chemical-resistant gloves (nitrile recommended), and safety goggles. Work in a well-ventilated fume hood to minimize inhalation of dust or aerosols.

Storage: Store the compound in a tightly sealed container in a cool (15–25 °C), dry location away from direct light, moisture, and incompatible oxidizing agents. Avoid prolonged exposure to air to prevent potential hygroscopic degradation of the solid.

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

Stability: The compound is expected to be stable under recommended storage conditions for extended periods; however, the actual shelf life should be confirmed with the Certificate of Analysis (CoA) supplied with each lot. Purity should be verified by HPLC or NMR prior to use in sensitive biological assays.

Quality and Ordering Information

Aladdin Scientific supplies 5-Bromo-6-methyl-1H-benzo[d]imidazole under catalog number B681029. Each lot is supported by a Certificate of Analysis (CoA) documenting purity and physicochemical characterization data.

Recommended Purity Verification: Before committing the compound to a multi-step synthesis or biological assay, researchers should verify purity by at least one orthogonal analytical technique, such as reverse-phase HPLC and ¹H NMR. Pay particular attention to regiochemical identity when using 2D NMR (COSY, HMBC) to confirm the substitution pattern relative to other commercially available positional isomers.

Available Pack Sizes: Multiple pack sizes may be available to suit discovery-scale and scale-up requirements. Contact Aladdin Scientific or visit the product page for current stock status, pricing, and bulk quotation.

Custom Synthesis: For quantities or specifications beyond standard catalog offerings, Aladdin Scientific can facilitate custom synthesis inquiries through its supplier network.