(4-Bromophenyl)diphenylphosphine
[CAS# 734-59-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (4-Bromophenyl)diphenylphosphine
• Molecular Formula: C₁₈H₁₄BrP
• Molecular Weight: 341.18
• CAS Registry Number: 734-59-8
• EC Number: 211-996-3
• SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=C(C=C3)Br

Properties

• Boiling Point: 397.5±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 194.2±23.2 °C, Calc.^*

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

Safety Data

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

Discovery and Applications

(4-Bromophenyl)diphenylphosphine, a versatile organophosphorus compound, has garnered significant attention in the field of organic synthesis and catalysis. This compound is noted for its effectiveness as a ligand in palladium-catalyzed cross-coupling reactions, particularly in the Suzuki-Miyaura coupling process.

The discovery of (4-Bromophenyl)diphenylphosphine can be traced back to advancements in organophosphorus chemistry, where researchers aimed to develop phosphine ligands that could enhance the efficiency and selectivity of catalytic reactions. This compound is characterized by the presence of a bromine atom attached to a phenyl group, which, in turn, is bonded to a diphenylphosphine group. The bromine atom's presence is crucial as it provides additional functionality that can influence the electronic properties of the phosphine ligand.

One of the primary applications of (4-Bromophenyl)diphenylphosphine is in palladium-catalyzed cross-coupling reactions, which are fundamental to the formation of carbon-carbon bonds in organic synthesis. In these reactions, (4-Bromophenyl)diphenylphosphine acts as a ligand that stabilizes the palladium catalyst, facilitating the coupling of aryl halides with various nucleophiles, such as organoboron compounds. The effectiveness of this ligand in these processes is attributed to its ability to provide electronic and steric support to the palladium center, thereby enhancing the reaction's efficiency.

The Suzuki-Miyaura coupling reaction, in particular, benefits from the use of (4-Bromophenyl)diphenylphosphine. This reaction, which couples aryl halides with aryl or vinyl boronic acids, is widely used to synthesize biaryl compounds and other complex organic molecules. The ligand's ability to improve the reaction's rate and yield makes it a valuable tool in both academic and industrial settings.

In addition to its role in cross-coupling reactions, (4-Bromophenyl)diphenylphosphine has also been explored for its potential in other catalytic applications. Its unique electronic properties make it a candidate for use in various types of catalytic transformations, including those that involve the activation of small molecules or the formation of new chemical bonds.

Overall, the discovery and application of (4-Bromophenyl)diphenylphosphine represent a significant advancement in the field of organophosphorus chemistry and catalysis. Its ability to enhance the performance of palladium catalysts in cross-coupling reactions has made it a valuable reagent in synthetic chemistry, contributing to the development of new materials and pharmaceuticals.

References

Jihoon Shin, Julie Bertoia, Kenneth R. Czerwinski and Chulsung Bae. A new homogeneous polymer support based on syndiotactic polystyrene and its application in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, Green Chem., 2009, 11, 1576.