What Is 8-Amino-5-bromoisoquinoline?

8-Amino-5-bromoisoquinoline (CAS not verified; SKU A188021) is a bifunctionally substituted isoquinoline heterocycle bearing a primary amino group at the 8-position and a bromine atom at the 5-position. The isoquinoline core is a nitrogen-containing bicyclic aromatic system closely related to quinoline and naphthalene, and is a privileged scaffold in pharmaceutical research. The simultaneous presence of a nucleophilic amine and an electrophilic aryl bromide on the same ring system makes this compound particularly valuable as a dual-handle building block for the construction of more complex molecular architectures via condensation, acylation, sulfonylation, and transition-metal-catalyzed cross-coupling reactions.

Key Chemical and Physical Properties

8-Amino-5-bromoisoquinoline has the molecular formula C₉H₇BrN₂ and a molecular weight of approximately 223.07 g/mol. As an aromatic heterocycle with electron-donating (–NH₂) and electron-withdrawing (Br) substituents, its electronic properties are asymmetrically distributed across the ring, influencing its reactivity in both electrophilic and nucleophilic transformations. The compound is expected to appear as a solid at room temperature; specific melting point, solubility, and appearance data should be confirmed from the product certificate of analysis (CoA) supplied by Aladdin Scientific. Solubility is anticipated in polar aprotic solvents such as DMSO and DMF, as is common for aminobromoisoquinolines, though laboratory verification is recommended.

Research and Synthetic Applications

The dual functionality of 8-Amino-5-bromoisoquinoline makes it a versatile intermediate in multiple synthetic strategies:

• Palladium-catalyzed cross-coupling: The aryl bromide at C-5 is a competent electrophile for Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira coupling reactions, enabling introduction of aryl, heteroaryl, amino, or alkynyl groups.
• Amine derivatization: The C-8 primary amine can be acylated, sulfonylated, reductively alkylated, or used in condensation reactions to form amides, sulfonamides, imines, or ureas.
• Kinase inhibitor and drug scaffold synthesis: Isoquinoline derivatives are well-represented in medicinal chemistry libraries targeting kinases, GPCRs, and other protein families; the aminobromo substitution pattern is particularly useful for building inhibitor scaffolds.
• Heterocyclic library construction: Sequential or one-pot exploitation of both reactive sites supports diversity-oriented synthesis (DOS) approaches.

Researchers should consult primary literature for specific reaction conditions optimized for this substrate.

Storage, Handling, and Safety

As an aromatic amine and organobromine compound, 8-Amino-5-bromoisoquinoline should be handled with standard laboratory precautions:

• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area, away from light and moisture. Refrigerated storage (2–8 °C) is commonly recommended for amino-heterocycles to prevent oxidation or degradation; confirm with the Aladdin CoA.
• Personal protective equipment: Use appropriate gloves, lab coat, and eye protection. Avoid inhalation of dust.
• Disposal: Dispose of as chemical waste in accordance with local regulations.
• Stability: The primary amine is susceptible to oxidation on prolonged exposure to air; minimize exposure time outside storage conditions.

Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for authoritative hazard and first-aid information before use.

Ordering and Availability from Aladdin Scientific

8-Amino-5-bromoisoquinoline is available from Aladdin Scientific under SKU A188021. When ordering, researchers should:

• Confirm the required quantity and purity grade for their application (analytical, synthetic, or screening grade).
• Request or download the Certificate of Analysis (CoA) and Safety Data Sheet (SDS) from the Aladdin Scientific website or customer service team.
• Inquire about bulk pricing, custom packaging, or expedited shipping options if needed.
• Check current stock availability and lead times through the online catalog or by contacting the Aladdin Scientific sales team directly.

For technical questions about this product, contact Aladdin Scientific's technical support team via the website or email.