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Intermediates&Fine Chemicals

1,8-Dibromonaphtalene

Category:

Intermediates&Fine Chemicals

CAS NO:

17135-74-9

Standard:

In-house Standards,

Price Range:

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North America,Central/South America,Western Europe,Eastern Europe,Australasia,Eastern Europe,Australasia,Asia,Middle East,Africa

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Hangzhou Verychem Science And Technology Co.Ltd.

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Basic Info

CAS Number

17135-74-9

Pharmacopoeia

In-house Standards

Grade

pharmaceutical grade

Is Manufacturer

YES

Samples Provided

Product Description

pharmaceutical intermediates

AI Product Description

*The following content is generated by AI and is for reference only.

1,8-Dibromonaphthalene is a specialized organic halide derived from the naphthalene structure, characterized by bromine atoms substituted at the 1 and 8 positions on the aromatic ring system. Its molecular formula is C₁₀H₆Br₂, and it carries the CAS Registry Number 576-49-2. This compound typically appears as a pale yellow to off-white crystalline solid with a distinct melting point ranging between 108°C and 111°C. Due to its specific substitution pattern, 1,8-dibromonaphthalene exhibits unique steric and electronic properties that distinguish it from other dibrominated naphthalene isomers, making it highly valuable in advanced chemical synthesis. The primary application of this reagent lies in medicinal chemistry and materials science, where it serves as a crucial building block for constructing complex heterocyclic frameworks. Chemists frequently utilize it in palladium-catalyzed cross-coupling reactions, such as Suzuki-Miyaura or Sonogashira couplings, to introduce diverse functional groups onto the naphthalene core. These transformations are essential for synthesizing pharmaceutical intermediates, fluorescent probes, and liquid crystals used in display technologies. Furthermore, the presence of two reactive bromine sites allows for sequential functionalization, enabling the creation of highly substituted derivatives with tailored optical and electronic characteristics. In the field of supramolecular chemistry, 1,8-dibromonaphthalene acts as a rigid spacer or ligand precursor, facilitating the assembly of metal-organic frameworks (MOFs) and coordination polymers. Its structural rigidity helps maintain defined geometries within these macroscopic assemblies, which is critical for applications in gas storage and separation. Additionally, researchers explore its potential in developing novel organic semiconductors and photovoltaic materials, leveraging its conjugated π-system to enhance charge transport properties. While not a commodity chemical, 1,8-dibromonaphthalene remains an indispensable tool for academic research and high-value industrial processes requiring precise molecular architecture. Safety protocols must be observed during handling, as organic bromides can be irritants and require proper ventilation. Overall, this versatile intermediate continues to play a pivotal role in advancing synthetic methodologies and material innovation across multiple scientific disciplines.