For chemists and materials scientists, understanding the fundamental chemical properties and synthesis routes of key intermediates is essential for driving innovation. 2-Bromo-9,9-dihexylfluorene (CAS 226070-05-9) is a prime example of such a compound, increasingly recognized for its utility in advanced organic synthesis and material science, particularly within the realm of organic electronics. As a specialized chemical manufacturer and supplier, we offer a detailed look at this important molecule, providing valuable insights for researchers and procurement professionals.

Unpacking the Chemical Structure and Properties

2-Bromo-9,9-dihexylfluorene possesses a molecular formula of C25H33Br, with a molecular weight of approximately 413.43 g/mol. Its structure is characterized by a fluorene core, a rigid aromatic system that confers stability. At the C9 position, two n-hexyl chains are attached. These long alkyl chains are critical as they significantly enhance the solubility of the molecule in common organic solvents like tetrahydrofuran (THF), toluene, chloroform, and dichloromethane. This improved solubility is a major advantage, simplifying reaction setup, purification (e.g., column chromatography), and processing for applications that require solution-based methods.

The presence of a bromine atom at the C2 position is the compound's most synthetically important feature. Bromine is an excellent leaving group and a versatile functional handle, making 2-Bromo-9,9-dihexylfluorene an ideal substrate for a variety of palladium-catalyzed cross-coupling reactions. These reactions allow for the selective formation of new carbon-carbon bonds, enabling the extension of conjugation and the construction of complex polymeric or oligomeric structures essential for advanced materials.

Synthesis of 2-Bromo-9,9-dihexylfluorene: A Typical Approach

The synthesis of 2-Bromo-9,9-dihexylfluorene typically involves a multi-step process starting from readily available precursors. A common route often begins with fluorene or 2-bromofluorene. The key steps usually involve:

  1. Alkylation at C9: Fluorene or 2-bromofluorene is reacted with a strong base (like sodium hydroxide or potassium hydroxide) in the presence of a phase-transfer catalyst (e.g., tetrabutylammonium bromide) and an alkylating agent, typically 1-bromohexane. This step introduces the two n-hexyl chains at the sp3 hybridized C9 position. The reaction conditions, including temperature and reagent ratios, are optimized to ensure efficient dialkylation and minimize side products.
  2. Bromination (if starting from fluorene): If the starting material is fluorene, a bromination step is required to introduce the bromine at the C2 position. This is usually achieved using brominating agents like N-bromosuccinimide (NBS) or elemental bromine under controlled conditions to ensure regioselectivity.

The final product is typically purified using column chromatography over silica gel, yielding 2-Bromo-9,9-dihexylfluorene as a solid or a viscous liquid, often with a yellow hue. As a manufacturer, we employ optimized protocols to achieve high yields and purity, ensuring that the product meets the stringent specifications required by R&D professionals.

Procurement for R&D: Choosing a Reliable Supplier

For research and development purposes, access to high-quality, reliable intermediates is non-negotiable. When you need to buy 2-Bromo-9,9-dihexylfluorene, look for suppliers who provide detailed product specifications, including purity levels (often confirmed by NMR spectroscopy), and offer consistent product quality. As a leading chemical supplier in China, we are committed to providing precisely these assurances. We understand the importance of timely delivery for research projects and offer various packaging sizes suitable for laboratory use. Contact us for a quote and to discuss your specific needs for this versatile organic synthesis intermediate.