In the vast landscape of chemical synthesis, certain molecules stand out for their versatility and critical role in creating advanced materials and compounds. 1,4-Dibromonaphthalene, identified by its CAS number 83-53-4, is one such compound. NINGBO INNO PHARMCHEM CO.,LTD. highlights the significance of this dibrominated naphthalene derivative as a fundamental intermediate for numerous applications, ranging from cutting-edge organic electronics to life-saving pharmaceuticals.

Understanding the Chemical Profile of 1,4-Dibromonaphthalene

1,4-Dibromonaphthalene, with the chemical formula C10H6Br2, is a crystalline powder that typically appears as white to off-white or light orange-beige. Its molecular weight is approximately 285.96 g/mol, and it exhibits a melting point in the range of 80-82°C. The key to its utility lies in the presence of two bromine atoms strategically placed at the 1 and 4 positions on the naphthalene ring. This configuration makes it highly reactive in various organic transformations, particularly in carbon-carbon bond-forming reactions.

Key Reactions and Synthetic Utility

The primary synthetic value of 1,4-Dibromonaphthalene stems from its participation in palladium-catalyzed cross-coupling reactions. These include:

  • Suzuki-Miyaura Coupling: This reaction allows for the efficient formation of carbon-carbon bonds by reacting 1,4-Dibromonaphthalene with organoboron compounds. This is a crucial step in building complex molecular structures for both pharmaceuticals and advanced materials.
  • Heck Coupling: Another important palladium-catalyzed reaction, the Heck coupling, enables the alkenylation of aryl or vinyl halides. 1,4-Dibromonaphthalene readily participates in this reaction, allowing for the introduction of vinyl groups and further functionalization of the naphthalene core.
  • Halogen-Metal Exchange: The bromine atoms can also undergo halogen-metal exchange reactions, typically with organolithium or Grignard reagents, to generate organometallic intermediates. These intermediates are highly reactive and can be further reacted with various electrophiles, expanding the synthetic possibilities.

These reactions make 1,4-Dibromonaphthalene an indispensable building block for chemists aiming to synthesize novel compounds with specific properties.

Applications Across Industries

The synthetic versatility of 1,4-Dibromonaphthalene translates into a broad spectrum of applications:

  • Organic Electronics: It is a key precursor in the synthesis of materials for OLEDs and organic photovoltaic (OPV) devices. Its derivatives are used to create charge transport layers, emitters, and other functional components that dictate the performance of these electronic devices.
  • Pharmaceuticals: In drug discovery, 1,4-dibromonaphthalene serves as a starting material for synthesizing potential therapeutic agents. Its derivatives have shown promise in areas such as enzyme inhibition, antimicrobial activity, and anticancer research.
  • Materials Science: The compound is used to develop a variety of functional materials, including polymers and advanced porous frameworks, leveraging its unique structure and reactivity.

As a leading 1,4-Dibromonaphthalene manufacturer in China, NINGBO INNO PHARMCHEM CO.,LTD. is committed to providing high-purity material that meets the exacting standards of chemical synthesis. Our reliable supply ensures that researchers and manufacturers can effectively harness the potential of this versatile intermediate.