Chemical Identity and Physical Properties

6-Bromo-3-iodoquinoline (Aladdin SKU B734697) is a bicyclic aromatic heterocycle consisting of a benzene ring fused to a pyridine ring (quinoline scaffold), substituted with bromine at the 6-position and iodine at the 3-position. The molecular formula is C₉H₅BrIN, giving a molecular weight of approximately 333.95 g/mol. The compound is typically a pale yellow to off-white crystalline solid at room temperature.

The quinoline core is an electron-deficient aromatic system due to the ring nitrogen, which influences the reactivity of both halogen substituents. The iodine at position 3 is particularly activated toward nucleophilic attack and oxidative addition because position 3 is adjacent to the electron-withdrawing nitrogen, whereas the bromine at position 6 resides on the carbocyclic ring, conferring a different electronic environment and reactivity profile.

Note: Precise melting point, boiling point, and solubility data should be verified against the certificate of analysis (CoA) supplied with each lot of B734697. Consult the Aladdin Scientific product page for the most current specification sheet.

Orthogonal Reactivity and Synthetic Applications

The principal synthetic value of 6-Bromo-3-iodoquinoline lies in the orthogonal reactivity of its two carbon–halogen bonds. Under palladium catalysis, C–I bonds undergo oxidative addition significantly faster than C–Br bonds, allowing chemists to perform selective transformations at the iodine-bearing carbon first, followed by a second distinct coupling at the bromine site.

This sequential selectivity supports a range of named reactions:

• Suzuki–Miyaura coupling: introduction of aryl or heteroaryl boronic acid partners selectively at C-3 (iodo) then C-6 (bromo).
• Sonogashira coupling: installation of terminal alkynes, useful for constructing conjugated systems or pharmaceutical pharmacophores.
• Negishi coupling: use of organozinc reagents for carbon–carbon bond formation.
• Buchwald–Hartwig amination: conversion of the C–Br bond to C–N bonds for amine-containing drug scaffolds.

Because the quinoline nucleus is a privileged scaffold in medicinal chemistry—present in antimalarial, antibacterial, antiviral, and kinase-inhibitor drug candidates—6-Bromo-3-iodoquinoline serves as a key starting material for library synthesis and lead optimisation programs.

Review flag: Specific literature examples and reaction yields citing this exact compound should be verified before inclusion in publications.

Safe Handling, Storage, and Disposal

As with all organohalide reagents, 6-Bromo-3-iodoquinoline should be handled with appropriate laboratory precautions:

• Personal protective equipment (PPE): Wear nitrile or equivalent chemical-resistant gloves, a laboratory coat, and safety spectacles. Use respiratory protection if handling as a fine powder that may generate dust.
• Engineering controls: Work in a well-ventilated fume hood whenever weighing or dissolving the compound.
• Storage: Store in a tightly sealed container in a cool (2–25 °C recommended), dry, dark location away from incompatible materials such as strong oxidisers and strong bases. Desiccant storage is advisable to prevent moisture-mediated degradation.
• Spill management: Collect solid spills with a non-sparking tool, place in a labelled waste container, and dispose of in accordance with local regulations for organohalide waste.
• Disposal: Do not dispose of via drain or municipal waste streams. Follow institutional chemical waste disposal protocols and applicable environmental regulations.

Important: Always consult the Safety Data Sheet (SDS) for B734697 before first use. The SDS provides authoritative hazard classification, first-aid measures, and regulatory information specific to this lot.

Quality Specifications and Procurement Guidance

Aladdin Scientific supplies 6-Bromo-3-iodoquinoline under SKU B734697. When ordering, researchers and procurement staff should consider the following:

• Purity: Confirm the purity grade (typically ≥97% or ≥98% by HPLC or GC) stated on the current product listing and CoA. High purity is critical for sensitive cross-coupling reactions where trace metal or halide impurities can poison catalysts or reduce yields.
• Quantity options: Available pack sizes vary; contact Aladdin Scientific for bulk pricing or custom quantities required for large-scale synthesis campaigns.
• Lot-to-lot consistency: Request CoA documentation including NMR, HPLC, and elemental analysis or mass spectrometry data to verify identity and purity for each received lot.
• Lead time: Check current stock availability on the Aladdin Scientific website or contact customer service for estimated delivery timelines, particularly for larger quantities.

For questions about technical specifications, compatibility, or application support, contact Aladdin Scientific's technical support team directly.