Bis(2-diphenylphosphinophenyl) ether
[CAS# 166330-10-5]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Bis(2-diphenylphosphinophenyl) ether
• Synonyms: (Oxydi-2,1-phenylene)bis(diphenylphosphine)
• Molecular Formula: C₃₆H₂₈OP₂
• Molecular Weight: 538.55
• CAS Registry Number: 166330-10-5
• EC Number: 678-206-0
• SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6

Properties

• Melting point: 184-187 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335-H413
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Bis(2-diphenylphosphinophenyl) ether is a sophisticated chemical compound that has found significant applications in the field of coordination chemistry and catalysis. This substance is notable for its role as a versatile ligand in the synthesis and activation of metal complexes, which are crucial for various chemical transformations.

The discovery of Bis(2-diphenylphosphinophenyl) ether was motivated by the need for highly efficient and selective ligands in metal-catalyzed reactions. Researchers aimed to develop ligands that could stabilize metal centers while enhancing the reactivity and selectivity of catalytic processes. The ligand features a unique structure in which two diphenylphosphine groups are connected through an ether linkage, providing a rigid and planar framework that interacts effectively with metal ions.

The chemical structure of Bis(2-diphenylphosphinophenyl) ether consists of two 2-diphenylphosphinophenyl units linked by an ether group. This arrangement offers multiple coordination sites for metal ions, making it an excellent candidate for creating metal complexes with tailored reactivity and selectivity. The diphenylphosphine groups provide strong donor interactions with metal centers, while the ether linkage maintains structural rigidity and spatial arrangement.

One of the primary applications of Bis(2-diphenylphosphinophenyl) ether is in the field of homogeneous catalysis. The ligand is employed to form complexes with transition metals such as palladium, platinum, and rhodium. These metal-ligand complexes are used in a variety of catalytic reactions, including cross-coupling reactions like Suzuki and Heck reactions. These processes are essential for the formation of carbon-carbon bonds in the synthesis of complex organic molecules, including pharmaceuticals and advanced materials.

In addition to cross-coupling reactions, Bis(2-diphenylphosphinophenyl) ether is utilized in catalytic hydrogenation and hydroformylation reactions. In hydrogenation, the ligand-metal complex facilitates the addition of hydrogen to alkenes and ketones, producing saturated compounds with high selectivity. In hydroformylation, the ligand helps in the formation of aldehydes from alkenes, a crucial step in the synthesis of various industrial chemicals.

The stability and versatility of the Bis(2-diphenylphosphinophenyl) ether-metal complexes also make them useful in other catalytic processes, such as carbonylation and olefin polymerization. The ligand's ability to stabilize different metal oxidation states and coordination environments allows for the development of new catalytic systems with enhanced performance and selectivity.

Furthermore, the compound has been explored for its potential in material science. The metal complexes formed with Bis(2-diphenylphosphinophenyl) ether can be used to develop new materials with unique properties, such as conducting polymers and functionalized nanoparticles. These materials have applications in electronics, energy storage, and environmental remediation.

In summary, Bis(2-diphenylphosphinophenyl) ether is a significant ligand in the field of coordination chemistry and catalysis. Its unique structural features and versatile applications make it an important tool for developing efficient catalytic processes and advanced materials. The compound's discovery has paved the way for new methodologies in synthetic chemistry and materials science, highlighting its importance in both research and industrial applications.

References

2023. Palladium-catalyzed allylic alkylation enabled by ketone umpolung via Pudovik addition/[1,2]-phospha-Brook rearrangement. Science China Chemistry.
DOI: 10.1007/s11426-023-1744-2

2024. Highly regioselective synthesis of branched saturated aldehydes by tandem hydroformylation/isomerization/hydrogenation of 1-arylbutadienes. Monatshefte für Chemie - Chemical Monthly.
DOI: 10.1007/s00706-024-03224-1

2024. Construction of remote cyano-substituted quaternary carbon centers via nickel-catalyzed migratory hydrocyanation of unconjugated dienes. Science China Chemistry.
DOI: 10.1007/s11426-024-2182-9