(4-Bromophenyl)diphenylphosphine oxide
[CAS# 5525-40-6]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (4-Bromophenyl)diphenylphosphine oxide
• Synonyms: (p-Bromophenyl)diphenylphosphine oxide; 4-Bromophenyldiphenylphosphine oxide
• Molecular Formula: C₁₈H₁₄BrOP
• Molecular Weight: 357.18
• CAS Registry Number: 5525-40-6
• EC Number: 834-602-7
• SMILES: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)C3=CC=C(C=C3)Br

Properties

• Density: 1.43
• Boiling point: 498 °C
• Flash point: 255 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(4-Bromophenyl)diphenylphosphine oxide is a significant compound in the field of organophosphorus chemistry, notable for its utility in various chemical applications. This compound, featuring a phosphorus atom bonded to two phenyl groups and one brominated phenyl group, has garnered attention for its role in catalysis and material science. This article explores the discovery and applications of (4-Bromophenyl)diphenylphosphine oxide, underscoring its importance in contemporary chemical research.

The discovery of (4-Bromophenyl)diphenylphosphine oxide emerged from studies focused on developing novel organophosphorus compounds with enhanced properties for catalytic and material applications. The synthesis of this compound typically involves the oxidation of (4-bromophenyl)diphenylphosphine using various oxidizing agents, resulting in the formation of the corresponding phosphine oxide. The introduction of the bromine atom in the para position of the phenyl ring provides the compound with unique electronic and steric characteristics that influence its chemical behavior.

One of the primary applications of (4-Bromophenyl)diphenylphosphine oxide is in the field of catalysis. The compound is used as a ligand in the formation of metal complexes, which are employed in various catalytic reactions. The presence of the bromine atom in the phenyl ring enhances the electronic properties of the ligand, allowing it to form stable complexes with transition metals such as palladium, platinum, and rhodium. These metal-ligand complexes are utilized in a range of catalytic processes, including cross-coupling reactions, hydrogenation, and oxidative transformations. The compound's ability to modulate the electronic environment of the metal center contributes to improved catalytic activity and selectivity.

In addition to its catalytic applications, (4-Bromophenyl)diphenylphosphine oxide is also used in the synthesis of functional materials. The compound's phosphine oxide group can participate in various chemical reactions, including ligand exchange and coordination with metal centers. This reactivity makes it useful in the preparation of advanced materials, such as phosphorescent compounds and organometallic frameworks. The bromine substituent provides additional functionality, enabling the incorporation of the compound into complex molecular structures and materials.

The compound's properties make it valuable in the study of reaction mechanisms and coordination chemistry. Researchers use (4-Bromophenyl)diphenylphosphine oxide to investigate the behavior of metal complexes and to explore new catalytic systems. Its role in understanding the interaction between ligands and metal centers contributes to the development of more efficient and selective catalysts for various chemical transformations.

Handling (4-Bromophenyl)diphenylphosphine oxide requires standard laboratory precautions. The compound should be stored in a dry, inert atmosphere to prevent degradation. Proper safety measures should be observed when working with organophosphorus compounds, including the use of appropriate personal protective equipment.

Future research on (4-Bromophenyl)diphenylphosphine oxide may focus on expanding its applications in catalysis and materials science. Advances in understanding its coordination chemistry and reactivity could lead to the development of new catalytic systems and functional materials with enhanced properties.

References

2002. Ligands used for aqueous organometallic catalysis. Aqueous Organometallic Catalysis.
DOI: 10.1007/0-306-47510-3_2