(3-Bromophenyl)diphenylphosphine oxide
[CAS# 10212-04-1]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (3-Bromophenyl)diphenylphosphine oxide
• Synonyms: 1-bromo-3-diphenylphosphorylbenzene
• Molecular Formula: C₁₈H₁₄BrOP
• Molecular Weight: 357.18
• CAS Registry Number: 10212-04-1
• EC Number: 813-412-8
• SMILES: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)C3=CC(=CC=C3)Br

Properties

• Solubility: Practically insoluble (0.031 g/L) (25 ºC), Calc.^*
• Density: 1.43±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.648, Calc.^*
• Boiling Point: 507.4±42.0 ºC (760 mmHg), Calc.^*
• Flash Point: 260.7±27.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H412
• Precautionary Statements: P264-P264+P265-P273-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovory and Applicatios

(3-Bromophenyl)diphenylphosphine oxide is an organophosphorus compound that has gained attention for its unique chemical properties and applications in various fields, particularly in materials science and organic synthesis. This compound is characterized by a phosphorus atom bonded to a bromophenyl group and two phenyl groups, with an oxygen atom attached to the phosphorus, forming a phosphine oxide structure. The presence of the bromine atom in the phenyl ring adds further reactivity and versatility to the compound, making it useful for various synthetic transformations.

The discovery of (3-bromophenyl)diphenylphosphine oxide can be traced back to the broader efforts in the mid-20th century to develop new organophosphorus compounds with potential applications in both organic and inorganic chemistry. Researchers were particularly interested in phosphine oxides due to their stability and ability to act as ligands in coordination chemistry. The introduction of halogenated phenyl groups, such as the bromophenyl moiety, was a strategic move to enhance the compound's reactivity, allowing it to participate in a wider range of chemical reactions.

One of the most significant applications of (3-bromophenyl)diphenylphosphine oxide is in the field of organic synthesis. The bromine atom in the compound provides a site for further functionalization through various reactions, such as cross-coupling reactions, which are essential in the formation of carbon-carbon bonds. This makes the compound a valuable intermediate in the synthesis of more complex molecules, particularly in the pharmaceutical industry, where the ability to modify molecular structures with precision is crucial.

In addition to its role in organic synthesis, (3-bromophenyl)diphenylphosphine oxide has also been explored for its potential as a ligand in coordination chemistry. Phosphine oxides are known for their ability to stabilize metal centers, making them useful in the formation of metal complexes. These complexes are often employed in catalysis, where they can enhance the efficiency and selectivity of various chemical reactions. The presence of the bromophenyl group in this compound allows for the tuning of the electronic properties of the ligand, further increasing its utility in catalytic applications.

Another area where (3-bromophenyl)diphenylphosphine oxide has found application is in materials science. The compound's ability to form stable complexes with metals has led to its use in the development of new materials with specific electronic or optical properties. For example, metal-phosphine oxide complexes have been investigated for their potential use in organic light-emitting diodes (OLEDs) and other electronic devices, where the precise control of electronic properties is essential.

The development and application of (3-bromophenyl)diphenylphosphine oxide demonstrate the importance of organophosphorus chemistry in modern science. This compound's unique combination of reactivity, stability, and versatility makes it a valuable tool for researchers in various fields. Its role as an intermediate in organic synthesis, a ligand in coordination chemistry, and a component in materials science highlights the broad range of applications that can be achieved through the careful design and manipulation of molecular structures.

In summary, (3-bromophenyl)diphenylphosphine oxide represents a significant achievement in the field of organophosphorus chemistry. Its discovery has opened up new possibilities for the development of complex molecules and materials, underscoring the importance of continued research and innovation in this area. The compound's unique properties make it an essential tool for chemists working in organic synthesis, coordination chemistry, and materials science.