2-(Diphenylphosphino)bromobenzene
[CAS# 62336-24-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: 2-(Diphenylphosphino)bromobenzene
• Synonyms: 2-(Diphenylphosphino)phenyl bromide
• Molecular Formula: C₁₈H₁₄BrP
• Molecular Weight: 341.18
• CAS Registry Number: 62336-24-7
• EC Number: 263-515-1
• SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3Br

Properties

• Solubility: Insoluble (5.1E^-5 g/L) (25 ºC), Calc.^*
• Melting point: 125 ºC (ethyl ether ligroine )^**

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

^** Quintard, Delphine; Synthesis 2004, (6), P905-908.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P280-P305+P351+P338

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

Discovory and Applicatios

2-(Diphenylphosphino)bromobenzene, often abbreviated as DPPB, is a notable organophosphorus compound that has made significant contributions to the field of organometallic chemistry. This compound was first synthesized in the early 1980s as part of efforts to develop new ligands for transition metal catalysis. The synthesis involves a two-step process, beginning with the bromination of bromobenzene to yield 2-bromobenzene. This intermediate is then reacted with diphenylphosphine to produce 2-(diphenylphosphino)bromobenzene.

As a ligand, 2-(diphenylphosphino)bromobenzene is characterized by its ability to stabilize metal centers through coordination with the phosphorus atom. The presence of the bromine substituent at the ortho position of the benzene ring adds an additional element of electronic and steric influence, which can be advantageous in various catalytic processes. The diphenylphosphino group provides strong donor properties due to the presence of two phenyl rings, which can interact favorably with metal centers.

One of the key applications of 2-(diphenylphosphino)bromobenzene is in the realm of palladium-catalyzed cross-coupling reactions. In these reactions, such as the Suzuki-Miyaura or Heck coupling, the ligand plays a crucial role in stabilizing the palladium center and facilitating the coupling between organic substrates. The effectiveness of the ligand in these reactions is largely due to its ability to provide a favorable environment for the palladium catalyst, thus improving the reaction efficiency and selectivity.

Additionally, 2-(diphenylphosphino)bromobenzene is employed in other catalytic processes, including hydroformylation and carbonylation. The compound's ability to stabilize metal complexes and influence their reactivity makes it valuable in designing and optimizing catalytic systems for these reactions. Its application extends to the synthesis of complex organic molecules and materials, where control over reaction pathways is essential for achieving desired outcomes.

The discovery and development of 2-(diphenylphosphino)bromobenzene have had a lasting impact on the field of organometallic chemistry. The compound's role as a ligand has facilitated advancements in various catalytic methodologies, demonstrating its utility in both academic research and industrial applications. Ongoing research continues to explore new ways to utilize and improve upon this ligand, underscoring its significance in advancing chemical synthesis and materials science.

References

M. L. Williams, C. L. Noack, R. J. Saverin and P. C. Healy. (2-Bromophenyl)diphenylphosphine, Acta Cryst. (2002). E58, o306-o307�