For scientists and engineers in the chemical industry, a deep understanding of the synthesis and applications of key chemical intermediates is crucial for innovation. 3,6-Dibromophenanthrene (CAS 174735-02-5) stands out as a versatile molecule with significant utility in advanced organic synthesis and materials science. This article explores the scientific underpinnings of this compound, from its production to its functional applications, and provides guidance on how to effectively procure it.

Synthesis of 3,6-Dibromophenanthrene: Chemical Pathways

The synthesis of 3,6-Dibromophenanthrene, a derivative of phenanthrene, primarily involves electrophilic aromatic substitution. A common laboratory and industrial method is the direct bromination of phenanthrene. This process typically uses elemental bromine (Br₂) as the brominating agent. The reaction is often carried out in a suitable solvent, such as nitrobenzene or acetic acid, and may involve catalysts like iron(III) bromide or benzoyl peroxide to facilitate the reaction and control regioselectivity. For example, reacting phenanthrene with bromine in nitrobenzene at reflux temperatures is a documented route. Achieving high yields and purity of the desired 3,6-dibrominated isomer requires precise control over reaction temperature, time, and the stoichiometry of reactants. Manufacturers focus on optimizing these parameters to produce material with a minimum purity of 97%.

Another important related compound is 3,6-Dibromo-phenanthrenequinone (CAS 53348-05-3). Its synthesis can be achieved by oxidizing 3,6-dibromophenanthrene or by direct bromination of phenanthrene-9,10-quinone. The scientific literature provides detailed procedures for these transformations, which are critical for researchers seeking to buy 3,6-dibromophenanthrene or its oxidized form for specific research needs.

Applications: A Cornerstone of Modern Chemistry

The strategic placement of bromine atoms on the phenanthrene core makes 3,6-Dibromophenanthrene an exceptional building block for constructing complex molecular architectures. Its applications are widespread:

  • Macrocyclic Synthesis: It is a key monomer in the synthesis of cyclic oligophenanthrenes. These macrocycles are synthesized via Yamamoto-type coupling reactions, catalyzed by nickel complexes. The resulting structures are investigated for their unique electronic and photophysical properties.
  • Cross-Coupling Chemistry: The aryl bromide functionalities are highly reactive in palladium-catalyzed cross-coupling reactions such as Suzuki, Stille, Heck, and Sonogashira couplings. This versatility allows for the precise introduction of various substituents, leading to functionalized phenanthrene derivatives. These derivatives are vital for developing organic electronic materials, including those used in OLEDs, organic semiconductors, and advanced polymers.
  • Pharmaceutical and Agrochemical Intermediates: As a reactive intermediate, it can be utilized in the synthetic pathways of complex biologically active molecules.

When considering the 3,6-dibromophenanthrene price, it is important to factor in the synthesis complexity and purity requirements, especially for specialized applications. A reliable supplier in China can often provide competitive pricing for bulk orders.

Quality and Procurement Insights

For scientists and procurement managers, sourcing high-quality 3,6-Dibromophenanthrene is paramount. Ensuring the material meets stringent purity standards (e.g., ≥97%) is essential for the reproducibility of synthetic reactions and the performance of the final products. Manufacturers provide detailed technical specifications and Certificates of Analysis (CoA) to verify product quality. When exploring options to buy this chemical, prioritize suppliers with established reputations for quality and consistent supply.

Conclusion

3,6-Dibromophenanthrene is a chemically significant intermediate, underpinning advancements in materials science, organic synthesis, and potentially pharmaceutical development. Its synthesis pathways are well-defined, and its reactivity in modern coupling chemistries makes it an invaluable tool for creating sophisticated molecular structures. By understanding its scientific properties and working with trusted manufacturers and suppliers, researchers can effectively leverage 3,6-Dibromophenanthrene to push the boundaries of chemical innovation.