Chemical Identity and Structure

9-Benzyl-3-bromo-9H-carbazole (SKU B152000) belongs to the carbazole family of tricyclic aromatic nitrogen heterocycles. The parent carbazole scaffold consists of two benzene rings fused to a central pyrrole ring, conferring a rigid planar π-system with excellent charge-transport properties. In this compound, two structural modifications are introduced relative to unsubstituted carbazole: (1) a benzyl group attached to the nitrogen atom at position 9, which increases solubility in common organic solvents and prevents N–H reactivity, and (2) a bromine atom at the C-3 position, which serves as a handle for downstream functionalization via metal-catalyzed cross-coupling chemistry.

The combination of an electron-rich carbazole core with an aryl bromide electrophilic site makes this molecule a bifunctional building block. The N-benzyl group also provides steric and electronic modulation of the carbazole nitrogen, influencing both the compound's photophysical properties and its behavior in palladium-catalyzed reactions.

Synthetic Applications and Reactivity

The C-3 aryl bromide of 9-Benzyl-3-bromo-9H-carbazole is the primary site for chemical elaboration. Researchers routinely employ this compound in the following reaction classes:

• Suzuki–Miyaura Coupling: Reaction with arylboronic acids under palladium catalysis installs aryl or heteroaryl groups at C-3, enabling access to 3,9-disubstituted carbazole frameworks relevant to organic light-emitting diodes (OLEDs) and hole-transport materials.
• Buchwald–Hartwig Amination: Pd-catalyzed C–N bond formation allows introduction of diarylamine or carbazolyl moieties at C-3, a common strategy in the synthesis of emissive materials with thermally activated delayed fluorescence (TADF).
• Miyaura Borylation: Conversion of the aryl bromide to the corresponding boronic ester (e.g., Bpin) provides a complementary nucleophilic partner for further coupling steps.
• Lithiation/Metal–Halogen Exchange: Treatment with n-BuLi at low temperature generates a C-3 aryllithium species amenable to addition to electrophiles such as aldehydes, ketones, and carbon dioxide.

In medicinal chemistry, carbazole derivatives bearing halogens at the 3-position have been explored as scaffolds for kinase inhibitors and antimicrobial agents, though specific biological data for this exact compound should be verified against primary literature.

Handling, Safety, and Storage Guidelines

As with all organobromine aromatic compounds, 9-Benzyl-3-bromo-9H-carbazole should be handled with standard laboratory precautions. Researchers and lab managers are advised to observe the following guidelines pending review of the product-specific Safety Data Sheet (SDS):

• Personal Protective Equipment (PPE): Wear nitrile gloves, a lab coat, and safety goggles when weighing or handling the compound. Use a fume hood to minimize 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 label), dry, well-ventilated area away from direct light, moisture, and incompatible materials such as strong oxidizers and bases.
• Disposal: Dispose of waste material in accordance with local, regional, and national regulations governing aromatic halogenated compounds.
• Spill Management: Collect solid material carefully to avoid dust generation; transfer to a labeled waste container.

Note: The specific hazard classification, GHS pictograms, and first-aid measures must be confirmed from the official SDS provided by Aladdin Scientific for SKU B152000. Do not rely solely on this guideline for safety decisions.

Purity, Quality Specifications, and Ordering

Aladdin Scientific supplies 9-Benzyl-3-bromo-9H-carbazole under SKU B152000. When evaluating this reagent for your research, consider the following quality parameters:

• Purity: Confirm the stated purity (typically assessed by HPLC or GC) from the certificate of analysis (CoA) available at the time of ordering. Higher purity grades are recommended for photophysical measurements and catalytic studies where trace impurities can affect quantum yield or turnover numbers.
• Analytical Characterization: Expect characterization data including ¹H NMR, ¹³C NMR, MS (or HRMS), and melting point. Request the CoA to verify lot-specific data before use.
• Available Pack Sizes: Contact Aladdin Scientific or visit the product page for current pack size options and pricing.
• Lead Time: Stock availability and lead times may vary; consult the product listing or contact customer service for procurement planning.

For bulk quantities or custom purity requirements, Aladdin Scientific's sales team can be contacted directly. Reward points, promotional pricing, and institutional account options may be available — see the Aladdin Scientific website for current offers.