1,2-Bis(diphenylphosphino)benzene
[CAS# 13991-08-7]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 1,2-Bis(diphenylphosphino)benzene
• Synonyms: (2-diphenylphosphanylphenyl)-diphenylphosphane
• Molecular Formula: C₃₀H₂₄P₂
• Molecular Weight: 446.46
• CAS Registry Number: 13991-08-7
• EC Number: 681-134-2
• SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3P(C4=CC=CC=C4)C5=CC=CC=C5

Properties

• Solubility: Insoluble (1.9E^-7 g/L) (25 °C), Calc.^*
• Melting point: 185-186 °C (toluene )^**

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

^** Baker, Benjamin A.

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

Discovery and Applications

1,2-Bis(diphenylphosphino)benzene is a prominent chemical compound in the field of organometallic chemistry, primarily recognized for its role as a versatile ligand in various catalytic applications. The compound's unique structure and properties make it an essential tool for enhancing the efficiency and selectivity of metal-catalyzed reactions.

The discovery of 1,2-Bis(diphenylphosphino)benzene can be traced back to the quest for more effective ligands in organometallic chemistry. This compound features a benzene ring with two diphenylphosphine groups attached at the 1,2-positions. This arrangement endows the molecule with both steric and electronic properties that are crucial for stabilizing metal centers and facilitating various chemical transformations.

In terms of application, 1,2-Bis(diphenylphosphino)benzene is particularly valuable in transition metal-catalyzed reactions. Its ability to form stable complexes with metals like palladium, platinum, and rhodium makes it an excellent ligand for promoting catalytic processes. One of its most notable uses is in cross-coupling reactions, such as Suzuki-Miyaura and Heck reactions, where it enhances the reactivity and selectivity of the metal catalyst.

The ligand's effectiveness is attributed to its bidentate nature, which allows it to form chelate complexes with metal centers. The presence of two phosphine groups in close proximity enables the formation of strong, stable metal-ligand bonds, thereby improving the catalyst's performance and longevity. This stability is particularly beneficial in reactions requiring prolonged or harsh conditions.

Another significant application of 1,2-Bis(diphenylphosphino)benzene is in hydrogenation reactions. The ligand's electronic properties facilitate the activation of hydrogen molecules, making it suitable for catalytic hydrogenation of alkenes and other substrates. This capability is valuable in various industrial processes, including the production of fine chemicals and pharmaceuticals.

The compound is also utilized in asymmetric synthesis, where it can be employed to develop chiral catalysts for enantioselective transformations. The ability to control the stereochemistry of reactions is crucial in the synthesis of complex molecules with high precision.

In addition to its applications in catalysis, 1,2-Bis(diphenylphosphino)benzene has been explored for use in materials science. Its coordination chemistry can be leveraged to create new materials with specific properties, such as enhanced electronic or optical characteristics.

Overall, 1,2-Bis(diphenylphosphino)benzene is a key ligand in organometallic chemistry, offering significant advantages in catalysis and materials science. Its discovery and development have provided valuable tools for advancing chemical reactions and synthesizing complex molecules, showcasing its importance in both academic research and industrial applications.

References

William Levason, Gillian Reid and Michael Webster . 1,2-Bis(diphenylphosphino)benzene and two related mono-methiodides, [o-C6H4(PR2)(PR2Me)]I (R = Ph or Me) , Acta Cryst (2006). C62, o438-o440