2-Bromobiphenyl
[CAS# 2052-07-5]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Hydrocarbon halide
• Name: 2-Bromobiphenyl
• Synonyms: 2-Bromo-1,1'-biphenyl
• Molecular Formula: C₁₂H₉Br
• Molecular Weight: 233.11
• CAS Registry Number: 2052-07-5
• EC Number: 218-141-3
• SMILES: C1=CC=C(C=C1)C2=CC=CC=C2Br

Properties

• Density: 1.352
• Melting point: 1.5-2 °C
• Boiling point: 297-298 °C
• Refractive index: 1.628-1.63
• Flash point: 113 °C
• Water solubility: Insoluble

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H319-H335-H400-H410
• Safety Statements: P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P391-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
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Bromobiphenyl is a noteworthy chemical compound in the realm of organic chemistry, characterized by its unique structural features and diverse applications. This substance is a brominated derivative of biphenyl, where a bromine atom is substituted onto the second carbon of the biphenyl structure. Its discovery and subsequent applications highlight its significance in various chemical processes and research fields.

The synthesis of 2-bromobiphenyl dates back to the early 20th century when chemists were developing methods for brominating biphenyl. The bromination reaction typically involves the electrophilic substitution of a bromine atom onto the biphenyl framework. This process is often carried out using bromine in the presence of a catalyst or under controlled conditions to ensure selective substitution. The resulting 2-bromobiphenyl exhibits distinct chemical properties due to the presence of the bromine atom, which influences its reactivity and interactions with other compounds.

One of the primary applications of 2-bromobiphenyl is in the field of organic synthesis. It serves as a crucial intermediate in the preparation of various organic compounds, including pharmaceuticals, agrochemicals, and advanced materials. The bromine substituent in 2-bromobiphenyl is a valuable functional group that facilitates further chemical modifications. For instance, it can be utilized in cross-coupling reactions, such as the Suzuki-Miyaura coupling, where it reacts with other nucleophiles to form biaryl structures with desired functional groups. This application is particularly significant in the synthesis of complex organic molecules used in drug discovery and material science.

Additionally, 2-bromobiphenyl plays a role in the development of organic electronic materials. Its structural properties make it a suitable candidate for the synthesis of organic semiconductors and light-emitting materials. The compound can be incorporated into conjugated systems to enhance the electronic and optical properties of the resulting materials. This application is important in the design and fabrication of organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and other electronic devices.

Another notable application of 2-bromobiphenyl is in the study of molecular interactions and chemical reactivity. Researchers use this compound to investigate the effects of bromine substitution on the electronic properties and reactivity of biphenyl derivatives. By analyzing the behavior of 2-bromobiphenyl in various chemical environments, scientists gain insights into the influence of substituents on molecular interactions, reaction mechanisms, and the overall stability of organic compounds.

The discovery and utilization of 2-bromobiphenyl underscore its importance in both synthetic chemistry and material science. Its ability to act as a versatile intermediate and its role in developing advanced materials highlight its significance in various research and industrial applications. Continued exploration of 2-bromobiphenyl contributes to advancements in organic synthesis, electronic materials, and the understanding of molecular interactions.

References

2021. Hypervalent Bromine(III) Compounds: Synthesis, Applications, Prospects. Synthesis, 53(22).
DOI: 10.1055/a-1675-8404

2020. Dienedioic acid as a useful diene building block via directed Heck-decarboxylate coupling. Communications Chemistry, 3(1).
DOI: 10.1038/s42004-020-0295-0

1976. Uptake of chloro- and bromobiphenyls, hexachloro- and hexabromobenzene by fish. Bulletin of Environmental Contamination and Toxicology, 16(6).
DOI: 10.1007/bf01685571