2,4'-Dibromobiphenyl
[CAS# 49602-91-7]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: 2,4'-Dibromobiphenyl
• Synonyms: 1-bromo-2-(4-bromophenyl)benzene
• Molecular Formula: C₁₂H₈Br₂
• Molecular Weight: 312.00
• CAS Registry Number: 49602-91-7
• SMILES: C1=CC=C(C(=C1)C2=CC=C(C=C2)Br)Br

Properties

• Density: 1.667g/mL
• Boiling point: 345.1 °C (760 mmHg)
• Flash point: 189.1 °C

Discovery and Applications

2,4'-Dibromobiphenyl is a significant organobromine compound known for its unique structure and versatile applications in organic synthesis and materials science. This compound features two bromine atoms attached to a biphenyl framework, specifically at the 2 and 4' positions, which imparts distinct chemical and physical properties.

The discovery of 2,4'-dibromobiphenyl was driven by the search for new brominated compounds with useful electronic and chemical characteristics. The presence of the bromine atoms on the biphenyl structure influences the molecule's reactivity and interaction with other substances, making it a valuable component in various chemical processes.

In organic synthesis, 2,4'-dibromobiphenyl is utilized as a versatile building block for constructing more complex molecules. Its structure allows it to participate in cross-coupling reactions, such as the Suzuki and Stille couplings, where it acts as a reactive substrate. These reactions are crucial in the formation of new carbon-carbon bonds, enabling the synthesis of complex organic compounds used in pharmaceuticals, agrochemicals, and advanced materials.

The compound also finds applications in the development of organic electronic materials. The bromine substituents contribute to the electronic properties of the biphenyl framework, which can be tailored for specific functions in organic semiconductors and light-emitting devices. 2,4'-Dibromobiphenyl is employed in the synthesis of organic light-emitting diodes (OLEDs) and organic photovoltaic cells, where its role is to modify the electronic and optical characteristics of the materials.

Additionally, 2,4'-dibromobiphenyl serves as an intermediate in the production of other brominated biphenyl derivatives, which are used in various industrial applications. Its stable and reactive nature makes it a key precursor in the synthesis of flame retardants and other specialty chemicals.

In summary, 2,4'-dibromobiphenyl is a valuable compound in both organic synthesis and materials science. Its unique structure, featuring bromine substituents on a biphenyl framework, makes it an important tool for creating complex organic molecules and developing advanced electronic materials.

References

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