Bis[2-((oxo)diphenylphosphino)phenyl] ether
[CAS# 808142-23-6]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: Bis[2-((oxo)diphenylphosphino)phenyl] ether
• Synonyms: Bis[2-(diphenylphosphino)phenyl] ether oxide
• Molecular Formula: C₃₆H₂₈O₃P₂
• Molecular Weight: 570.55
• CAS Registry Number: 808142-23-6
• SMILES: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(=O)(C5=CC=CC=C5)C6=CC=CC=C6

Properties

• Solubility: Insoluble (4.0E^-3 g/L) (25 °C), Calc.^*
• Density: 1.28±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 280 °C^** (Expl.)
• Index of Refraction: 1.671, Calc.^*
• Boiling Point: 753.3±60.0 °C (760 mmHg), Calc.^*
• Flash Point: 421.5±53.2 °C, Calc.^*

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

^** Han, Chunmiao

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Bis[2-((oxo)diphenylphosphino)phenyl] ether, often referred to as a phosphine oxide compound, is a specialized organophosphorus chemical with significant applications in coordination chemistry, catalysis, and material science. This compound consists of a central oxygen atom bonded to two phenyl groups, each of which is further substituted with a diphenylphosphino group that is oxidized to form a phosphine oxide. The molecular structure of bis[2-((oxo)diphenylphosphino)phenyl] ether is characterized by its coordination ability with transition metals, making it useful in a variety of catalytic processes.

The discovery of bis[2-((oxo)diphenylphosphino)phenyl] ether stems from the broader field of organophosphorus chemistry, where phosphines and their derivatives have long been recognized for their ability to interact with metal centers. Phosphines, when oxidized to phosphine oxides, exhibit enhanced stability and stronger interactions with metals, which are crucial for catalytic processes. The synthesis of bis[2-((oxo)diphenylphosphino)phenyl] ether involves the coupling of 2-((oxo)diphenylphosphino)phenyl groups with an oxygen atom, creating a bifunctional ligand that can effectively coordinate with metal ions.

One of the primary applications of bis[2-((oxo)diphenylphosphino)phenyl] ether is in the field of catalysis, particularly in transition metal-catalyzed reactions. Phosphine oxide ligands like this compound are commonly used in processes such as cross-coupling reactions, hydrogenation, and carbon-carbon bond formation. The electron-donating properties of the phosphine oxide group enable the coordination of metals such as palladium, platinum, and rhodium, facilitating various catalytic cycles. These catalytic processes are essential in the synthesis of fine chemicals, pharmaceuticals, and agrochemicals, where high selectivity and efficiency are required.

Another important application of bis[2-((oxo)diphenylphosphino)phenyl] ether is in the development of advanced materials. Due to its ability to coordinate with transition metals, this compound is utilized in the synthesis of metal-organic frameworks (MOFs) and other materials with specific properties, such as enhanced conductivity, magnetism, or optical characteristics. The precise control over the metal coordination environment offered by bis[2-((oxo)diphenylphosphino)phenyl] ether allows for the design of materials with tailored functions, making it valuable in fields such as electronics and energy storage.

In addition, bis[2-((oxo)diphenylphosphino)phenyl] ether has been explored for its potential role in organometallic chemistry and material science. Its ability to form stable complexes with metal ions, combined with its relatively simple structure, makes it an attractive ligand for various metal-catalyzed transformations. It also plays a role in enhancing the solubility of metal complexes in organic solvents, facilitating reactions in heterogeneous catalysis and solid-phase reactions.

Furthermore, this compound has been studied for its potential applications in the field of chemical sensing. Its ability to coordinate with metal ions can be leveraged to create sensors that detect the presence of specific metal ions in solution. Such sensors are crucial in environmental monitoring, where the detection of toxic metals is essential for ensuring water and soil quality.

In conclusion, bis[2-((oxo)diphenylphosphino)phenyl] ether is a versatile organophosphorus compound with a wide range of applications in catalysis, material science, and chemical sensing. Its ability to coordinate with transition metals and its stability in various chemical environments make it a valuable tool in the synthesis of complex materials and in catalytic processes. Ongoing research into its properties and applications will likely continue to expand its use in industrial and scientific advancements.

References

2010. Influence of phosphorus and oxygen donor diphosphine ligands on the reactivity of rhodium(I) carbonyl complexes. Journal of Molecular Catalysis A: Chemical, 326(1-2).
DOI: 10.1016/j.molcata.2010.05.008