Description

3-Bromonaphtho[2,3-b]benzofuran (CAS No. 1256544-32-7) is a high-purity brominated aromatic heterocyclic compound with the molecular formula C₁₆H₉BrO. This specialized chemical is designed for advanced research applications, particularly in organic synthesis, materials science, and pharmaceutical development. Its unique naphthobenzofuran scaffold, functionalized with a reactive bromine substituent, makes it a versatile building block for constructing complex polycyclic frameworks or as a precursor for cross-coupling reactions (e.g., Suzuki, Stille).

Available in rigorously controlled batches (typically ≥95% purity by HPLC), this compound is supplied as a crystalline solid with full spectroscopic characterization data (NMR, MS). Special handling under inert atmosphere is recommended due to potential sensitivity to oxidation. Researchers should store it at 2-8°C protected from light.

Key applications include: development of organic semiconductors, fluorescent probes, and as an intermediate for bioactive molecule synthesis. Technical specifications include molecular weight 297.15 g/mol, exact mass 295.9846 Da, and XLogP3 5.1.

Properties

• CAS Number: 1256544-32-7
• Complexity: 318
• IUPAC Name: 3-bromonaphtho[2,3-b]benzofuran
• InChI: InChI=1S/C16H9BrO/c17-12-5-6-13-14-7-10-3-1-2-4-11(10)8-15(14)18-16(13)9-12/h1-9H
• InChI Key: BBLXKCGFKPLRQK-UHFFFAOYSA-N
• Exact Mass: 295.98368
• Molecular Formula: C16H9BrO
• Molecular Weight: 297.14
• SMILES: C1=CC=C2C=C3C(=CC2=C1)C4=C(O3)C=C(C=C4)Br
• Topological: 13.1
• Monoisotopic Mass: 295.98368
• Synonyms: 3-Bromonaphtho[2,3-b]benzofuran, 1256544-32-7, Benzo[b]naphtho[2,3-d]furan,3-bromo-, SCHEMBL10122754, 3-bromonaphtho[2,3-b][1]benzofuran, 3-Bromo-benzo[b]naphtho[2,3-d]furan, BS-52211, CS-0437456, F72581

Application

This brominated benzofuran derivative serves as a critical intermediate in the synthesis of extended π-conjugated systems for organic electronic materials. Researchers utilize its reactivity in palladium-catalyzed cross-couplings to construct complex polycyclic aromatic hydrocarbons (PAHs) with tailored optoelectronic properties. The compound has shown utility in developing novel fluorescent markers for bioimaging studies due to its rigid, planar structure. Additionally, it finds use in medicinal chemistry as a scaffold for kinase inhibitor development.

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