Chemical Identity and Physical Properties

2-Amino-3-Bromo-5-chlorobenzonitrile (Aladdin SKU: A729818) is an ortho-amino benzonitrile derivative carrying both a bromine atom at the 3-position and a chlorine atom at the 5-position of the aromatic ring. Its molecular formula is C₇H₄BrClN₂. The compound possesses four distinct reactive sites: the primary amine, the nitrile group, the aryl bromide, and the aryl chloride. This combination of electron-donating (–NH₂) and electron-withdrawing (–CN, halogens) substituents creates a highly polarized aromatic system with differentiated reactivity at each halogen position, enabling selective functionalization under appropriate catalytic conditions.

Note: Specific physical constants (melting point, exact molecular weight, solubility data) should be confirmed against the current certificate of analysis (CoA) supplied with each lot from Aladdin Scientific.

Synthetic Applications and Reactivity

The four reactive functional groups of 2-Amino-3-Bromo-5-chlorobenzonitrile make it an exceptionally versatile building block in synthetic organic chemistry:

• Palladium-catalyzed cross-coupling: The aryl bromide (C3) is generally more reactive than the aryl chloride (C5) toward Suzuki–Miyaura, Negishi, Buchwald–Hartwig, and Heck coupling reactions under standard Pd(0)/Pd(II) catalysis. This chemoselectivity allows sequential functionalization—first at the bromide, then at the chloride using more active catalytic systems.
• Nitrile group transformations: The –CN group can be hydrolyzed to the corresponding carboxylic acid or amide, reduced to a primary amine, or engaged in cycloaddition reactions to form heterocyclic scaffolds such as tetrazoles and imidazoles.
• Amine chemistry: The primary –NH₂ group participates in acylation, sulfonylation, reductive amination, and condensation reactions, enabling construction of amide bonds or imine intermediates.
• Heterocycle synthesis: The spatial arrangement of –NH₂ and –CN at adjacent positions is particularly suited for annulation reactions leading to 2-aminobenzimidazoles, quinazolines, anthranilonitrile-derived scaffolds, and related N-heterocycles of pharmaceutical relevance.

Researchers should optimize reaction conditions (base, solvent, temperature, catalyst loading) for each specific transformation, as the electron-deficient character imposed by the nitrile and halogens affects nucleophilicity of the amine and reactivity of each C–halogen bond.

Handling, Safety, and Storage Guidelines

As with all aromatic halide and nitrile-containing compounds, appropriate laboratory safety practices must be followed when working with 2-Amino-3-Bromo-5-chlorobenzonitrile. Researchers and lab managers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

• Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves, laboratory coat, and safety goggles. Use a fume hood for all weighing and handling operations to minimize inhalation of dust or vapors.
• Storage: Store in a tightly sealed container in a cool (ideally 2–8 °C or as specified on the CoA), dry, and well-ventilated location, protected from light and moisture. Avoid contact with strong oxidizers, strong acids, and strong bases.
• Stability: The compound should remain stable under recommended storage conditions. Prolonged exposure to moisture or light may lead to degradation. Check for discoloration or unusual odor before use and verify purity by TLC or HPLC if the material has been stored for an extended period.
• Waste disposal: Dispose of according to local, regional, and national regulations for halogenated organic waste. Do not pour down the drain without appropriate treatment.

Specific toxicological data for this compound may be limited. All handling should apply the precautionary principle appropriate for reactive halogenated aromatics and nitriles.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies 2-Amino-3-Bromo-5-chlorobenzonitrile under catalog number A729818. To ensure experimental reproducibility, researchers should verify the following upon receipt:

• Certificate of Analysis (CoA): Confirms identity (by NMR and/or MS), purity (typically by HPLC or GC), and physical appearance. Always request the lot-specific CoA, available through the Aladdin Scientific website or customer service.
• Purity grade: Confirm the purity specification meets the requirements of your application. For sensitive catalytic or pharmaceutical applications, higher purity grades are recommended.
• Packaging: Available in multiple package sizes to suit screening quantities through larger preparative needs. Contact Aladdin Scientific procurement for custom quantities.
• Lead time and availability: Check current stock status on the Aladdin Scientific website or contact your regional sales representative for real-time inventory and delivery estimates.

For technical questions regarding product specifications, analytical data, or custom synthesis inquiries, contact Aladdin Scientific technical support.