4-Bromobiphenyl
[CAS# 92-66-0]

Identification

• Classification: Chemical pesticide >> Insecticide >> Rodenticide intermediate
• Name: 4-Bromobiphenyl
• Molecular Formula: C₁₂H₉Br
• Molecular Weight: 233.11
• CAS Registry Number: 92-66-0
• EC Number: 202-176-6
• SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)Br

Properties

• Density: 0.9327
• Melting point: 89-92 °C
• Boiling point: 310 °C
• Flash point: 143 °C
• Water solubility: Insoluble

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H302-H315-H318-H335-H400
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+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
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin corrosion	Skin Corr.	1B	H314

• Transport Information: UN 3152

Discovery and Applications

4-Bromobiphenyl is a versatile organic compound that has found widespread use in the fields of organic chemistry and material science. This compound, consisting of a biphenyl structure with a bromine substituent at the 4-position, exemplifies the intersection of halogenated aromatic compounds with advanced chemical applications.

The discovery of 4-Bromobiphenyl can be traced back to studies focusing on the functionalization of biphenyl derivatives. Biphenyl itself, a compound with two connected phenyl rings, has been a subject of interest due to its potential as a building block in various chemical transformations. The introduction of a bromine atom at the 4-position of one of the phenyl rings enhances the reactivity and introduces specific functional properties to the biphenyl structure.

4-Bromobiphenyl is synthesized through the bromination of biphenyl, typically using bromine or a brominating reagent under controlled conditions. The reaction proceeds with the selective substitution of a hydrogen atom on the biphenyl structure, resulting in the formation of 4-Bromobiphenyl. The synthesis process allows for precise control over the location of the bromine atom, which is crucial for its subsequent applications.

One of the significant applications of 4-Bromobiphenyl is in organic synthesis, particularly as a reagent in cross-coupling reactions. The bromine atom acts as a good leaving group, facilitating the formation of new carbon-carbon bonds. This property is utilized in Suzuki and Heck coupling reactions, where 4-Bromobiphenyl is employed to couple with various nucleophiles to form diverse biphenyl derivatives. These reactions are fundamental in the construction of complex organic molecules and materials.

In addition to its role in organic synthesis, 4-Bromobiphenyl is also used in the development of liquid crystal materials. Biphenyl derivatives are known for their applications in liquid crystal displays (LCDs) due to their ability to influence the liquid crystal phase. The presence of the bromine atom in 4-Bromobiphenyl can modify the thermal and optical properties of the liquid crystal phases, making it useful in the formulation of advanced display technologies.

Another application of 4-Bromobiphenyl is in the synthesis of various functional materials. For example, it is used as a starting material in the preparation of conducting polymers and other organic electronic materials. The bromine substituent can be used to introduce different functional groups, allowing for the customization of materials with specific electronic or optical properties.

4-Bromobiphenyl has also been studied for its potential in medicinal chemistry. The compound's ability to act as a building block for more complex structures makes it a candidate for the development of new pharmaceuticals. The bromine atom can influence the biological activity of the resulting compounds, offering opportunities for the creation of novel therapeutic agents.

In summary, 4-Bromobiphenyl is a valuable compound in both academic research and industrial applications. Its utility in organic synthesis, liquid crystal technology, and material science highlights its importance in advancing chemical and technological innovations. The ongoing study of 4-Bromobiphenyl and its derivatives continues to provide insights into new applications and methodologies in chemistry.

References

2023. Recyclable Pd nanoparticles immobilized on amine functionalized LDH for the Suzuki-Miyaura cross-coupling reaction. Chemical Papers, 77(11).
DOI: 10.1007/s11696-023-02885-2

2022. Recent Progress in C(sp2)-C(sp2) Bond Formation Using Ligand Coupling on Sulfur(IV). Synthesis, 54(22).
DOI: 10.1055/a-1912-1029

2020. Bimetallic Ni-Pd Synergism—Mixed Metal Catalysis of the Mizoroki-Heck Reaction and the Suzuki-Miyaura Coupling of Aryl Bromides. Catalysis Letters, 150(12).
DOI: 10.1007/s10562-020-03330-9