CAS · 5111-65-9
Product Overview
2-Bromo-6-methoxynaphthalene is a high-purity pharmaceutical-intermediates supplied for industrial and specialty chemical applications. Contact our team for specifications, packaging options and lead times.
Product Specifications
| Appearance: | White to Off-White to Light brown Powder |
|---|---|
| Purity: | 98.0%min |
Applications
1. Synthetic Intermediate in Organic Chemistry
Due to the presence of both a reactive bromine atom and an electron-donating methoxy group, 2-Bromo-6-methoxynaphthalene is a versatile intermediate in a variety of organic reactions:
Cross-Coupling Reactions:
Used in Suzuki, Stille, Sonogashira, and Heck coupling reactions to build complex biaryl or aryl-alkyne systems.
Facilitates C–C bond formation, especially for drug-like molecules and natural product analogs.
Lithiation and Nucleophilic Substitution:
The bromine can be replaced via metal-halogen exchange (e.g., using n-BuLi), followed by electrophilic trapping.
O-Demethylation:
The methoxy group can be selectively modified (e.g., converted to hydroxyl), giving access to hydroxynaphthalene derivatives.
2. Pharmaceutical and Medicinal Chemistry
2-Bromo-6-methoxynaphthalene serves as a key intermediate in the synthesis of biologically active compounds:
Aromatic pharmacophores: Naphthalene derivatives are common in pharmaceuticals due to their planar aromatic structure and bioactivity.
Lead compound development: Used in early-stage drug discovery to construct novel analogs of antitumor, antibacterial, or anti-inflammatory agents.
3. Fluorescent Dye and Material Synthesis
Methoxynaphthalene-based compounds are sometimes used in the design of:
Organic light-emitting diodes (OLEDs)
Fluorescent dyes or sensors
Photostable aromatic cores in advanced materials and polymers
Brominated derivatives like this are ideal for further functionalization, enabling fine-tuning of the molecule's optical or electronic properties.
4. Agrochemical Intermediates
It may also be employed in the synthesis of pesticides, herbicides, or fungicides, particularly those based on fused aromatic ring systems with halogen/methoxy functionality.
Benefits
1. Dual Functional Groups for Versatile Reactivity
The bromine atom allows for palladium-catalyzed cross-coupling, while the methoxy group can participate in electronic tuning, substitution, or demethylation.
2. Useful Scaffold for Drug Development
The naphthalene core is frequently found in medicinal chemistry due to its rigid aromatic structure and hydrophobic character-making it a valuable building block.
3. Stable and Easy to Handle
Solid at room temperature, with good shelf stability under proper storage conditions.
Suitable for scale-up in industrial or research settings.
4. Facilitates Structural Diversification
Allows medicinal chemists and material scientists to create structurally diverse libraries via late-stage functionalization.
Conclusion
2-Bromo-6-methoxynaphthalene (CAS 5111-65-9) is a highly useful intermediate in organic synthesis, prized for its dual reactivity and stable aromatic framework. It plays a vital role in cross-coupling chemistry, medicinal compound design, and materials science, especially where structural diversity and electronic modulation are required. Its versatility, ease of handling, and ability to participate in key bond-forming reactions make it a valuable building block in both research and industrial applications.
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