2-Bromo-4'-chloro-1,1'-biphenyl
[CAS# 179526-95-5]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: 2-Bromo-4'-chloro-1,1'-biphenyl
• Synonyms: 2-Bromo-4'-chlorobiphenyl
• Molecular Formula: C₁₂H₈BrCl
• Molecular Weight: 267.55
• CAS Registry Number: 179526-95-5
• EC Number: 821-244-1
• SMILES: C1=CC=C(C(=C1)C2=CC=C(C=C2)Cl)Br

Properties

• Density: 1.463

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2-Bromo-4'-chloro-1,1'-biphenyl is a halogenated biphenyl derivative with significant applications in organic chemistry and material science. This compound features two aromatic rings connected by a single bond, with bromine and chlorine substituents positioned on the phenyl rings. The presence of these halogen atoms imparts unique properties to the biphenyl structure, influencing its reactivity and potential uses.

The discovery of 2-Bromo-4'-chloro-1,1'-biphenyl dates back to the early 20th century when researchers began exploring the chemical behavior of substituted biphenyls. The introduction of halogen atoms into the biphenyl framework allows for modifications that can enhance its reactivity and application in various chemical processes.

One of the primary applications of 2-Bromo-4'-chloro-1,1'-biphenyl is in the synthesis of complex organic molecules. The bromine and chlorine substituents serve as valuable functional groups for cross-coupling reactions, such as Suzuki and Sonogashira couplings. These reactions are crucial for the formation of carbon-carbon bonds, enabling the construction of diverse organic compounds with potential applications in pharmaceuticals, agrochemicals, and materials science.

In material science, 2-Bromo-4'-chloro-1,1'-biphenyl is used as a building block for the synthesis of novel organic semiconductors. The presence of halogen atoms can influence the electronic properties of the biphenyl derivatives, making them suitable for applications in organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs). The compound's ability to modify electronic and optical properties makes it valuable for developing advanced materials with tailored characteristics.

Additionally, 2-Bromo-4'-chloro-1,1'-biphenyl plays a role in studying the fundamental properties of biphenyl derivatives. Researchers investigate its behavior in various chemical reactions and material applications to understand the effects of halogen substitution on the biphenyl system. This knowledge contributes to the development of new synthetic methodologies and materials with improved performance.

The compound's significance extends beyond its immediate applications. Its role as a versatile intermediate in organic synthesis and materials science highlights its importance in advancing chemical research and technology. As researchers continue to explore its properties and potential uses, 2-Bromo-4'-chloro-1,1'-biphenyl is expected to remain a valuable compound in the field of chemistry.

References

2018 Organolithium Reactions. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-228-00169