3-Bromobiphenyl
[CAS# 2113-57-7]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 3-Bromobiphenyl
• Synonyms: 3-bromobiphenyl
• Molecular Formula: C₁₂H₉Br
• Molecular Weight: 233.11
• CAS Registry Number: 2113-57-7
• EC Number: 218-304-9
• SMILES: C1=CC=C(C=C1)C2=CC(=CC=C2)Br

Properties

• Density: 1.398
• Boiling point: 299-301 ºC
• Refractive index: 1.637-1.641
• Flash point: 110 ºC
• Water solubility: Insoluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

3-Bromobiphenyl is a halogenated aromatic compound that consists of two benzene rings connected by a single bond, with a bromine atom attached to the third position of one of the rings. This chemical structure imparts significant reactivity and stability to the compound, making it useful in various applications, particularly in organic synthesis and materials science.

The discovery of 3-bromobiphenyl is closely tied to the broader study of biphenyl derivatives and halogenated aromatics. Early research into these compounds focused on their unique chemical properties and potential industrial applications. Halogenation, the process of introducing halogen atoms like bromine into organic molecules, was found to significantly alter the reactivity and physical properties of biphenyl, enabling the synthesis of more complex molecules. The bromine atom in 3-bromobiphenyl enhances its reactivity, particularly in cross-coupling reactions, which are widely used in the formation of carbon-carbon bonds in organic chemistry.

One of the primary applications of 3-bromobiphenyl is as an intermediate in organic synthesis. It serves as a starting material for the synthesis of more complex aromatic compounds, which are often used in pharmaceuticals, agrochemicals, and advanced materials. The compound’s bromine atom is particularly useful in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura coupling, which is a powerful tool for forming biaryl compounds. These reactions are essential in the development of various biologically active molecules, including potential drug candidates and agrochemicals.

In addition to its role in organic synthesis, 3-bromobiphenyl is also utilized in materials science. It can be incorporated into the synthesis of polymers and other materials that exhibit desirable electronic and optical properties. For example, 3-bromobiphenyl can be used as a building block in the production of organic semiconductors, which are crucial components in organic electronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). The compound's ability to facilitate the construction of conjugated systems makes it valuable for creating materials with specific electronic characteristics.

3-Bromobiphenyl also finds application in the study of environmental science and toxicology. Like other halogenated biphenyls, it is used as a model compound in research focused on understanding the behavior and impact of similar substances in the environment. While 3-bromobiphenyl is not as widely recognized as polychlorinated biphenyls (PCBs), its study contributes to the broader understanding of the environmental persistence and bioaccumulation of halogenated aromatic compounds. Research in this area is crucial for developing strategies to mitigate the environmental and health impacts of such substances.

Furthermore, 3-bromobiphenyl is used in the synthesis of various chemical probes and markers that are employed in biological research. These compounds are designed to interact with specific biological targets, allowing researchers to study cellular processes and disease mechanisms. The bromine atom in 3-bromobiphenyl facilitates the introduction of functional groups that can modify the compound’s interaction with biological systems, making it a versatile tool in chemical biology.

In recent years, the study of 3-bromobiphenyl has expanded to include its potential applications in the development of new materials and pharmaceuticals. Advances in synthetic methods, particularly in the area of cross-coupling reactions, have enabled the efficient and selective production of 3-bromobiphenyl and its derivatives. These developments have opened up new possibilities for the use of this compound in various fields, from drug discovery to the creation of advanced functional materials.

As research continues, 3-bromobiphenyl is likely to remain an important compound in both academic and industrial settings. Its unique combination of reactivity and stability ensures its ongoing relevance in the development of new synthetic methodologies and applications. The compound's role in the synthesis of complex organic molecules and materials underscores its significance in modern chemistry.

References

1984. Plasmid-Mediated Biodegradative Fate of Monohalogenated Biphenyls in Facultatively Anaerobic Sediments. Genetic Control of Environmental Pollutants.
DOI: 10.1007/978-1-4684-4715-6_8

2007. Biodegradation of diphenyl ether and transformation of selected brominated congeners by Sphingomonas sp. PH-07. Applied Microbiology and Biotechnology, 77(1).
DOI: 10.1007/s00253-007-1129-z

2022. Chemoselective borylation of bromoiodoarene in continuous flow: synthesis of bromoarylboronic acids. Journal of Flow Chemistry, 12(4).
DOI: 10.1007/s41981-022-00246-w