Bis[2-(dicyclohexylphosphino)phenyl] ether
[CAS# 434336-16-0]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Bis[2-(dicyclohexylphosphino)phenyl] ether
• Synonyms: dicyclohexyl-[2-(2-dicyclohexylphosphanylphenoxy)phenyl]phosphane
• Molecular Formula: C₃₆H₅₂OP₂
• Molecular Weight: 562.75
• CAS Registry Number: 434336-16-0
• EC Number: 687-020-9
• SMILES: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3OC4=CC=CC=C4P(C5CCCCC5)C6CCCCC6

Properties

• Solubility: Insoluble (3.9E^-8 g/L) (25 °C), Calc.^*
• Melting point: 140-146 °C

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Bis[2-(dicyclohexylphosphino)phenyl] ether, often abbreviated as Bis[2-(Cy2PhP)]O, is a noteworthy compound in the field of organophosphorus chemistry, characterized by its unique structure and versatile applications. This substance features two dicyclohexylphosphine groups attached to a central ether linkage, which imparts specific properties valuable in various chemical and industrial processes.

The discovery of Bis[2-(dicyclohexylphosphino)phenyl] ether stemmed from the ongoing exploration of phosphine-containing ligands that could enhance the performance of metal catalysts in organic synthesis. The synthesis of this compound involves the reaction of 2-(dicyclohexylphosphino)phenol with an appropriate etherifying agent. This process is typically carried out under controlled conditions to ensure high purity and yield of the product. Characterization techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and high-performance liquid chromatography (HPLC) are employed to confirm the structure and quality of the synthesized compound.

In the realm of catalysis, Bis[2-(dicyclohexylphosphino)phenyl] ether is primarily used as a ligand in various metal-catalyzed reactions. Its structure allows for effective coordination with metal centers, which enhances the reactivity and selectivity of the metal catalyst. This compound is particularly useful in catalytic processes such as cross-coupling reactions, including the Suzuki and Heck reactions, where it facilitates the formation of carbon-carbon bonds. The electron-donating properties of the phosphine groups contribute to the stabilization of metal intermediates, leading to improved reaction outcomes and efficiency.

The compound also finds applications in materials science, where it is used to synthesize functionalized polymers and other advanced materials. The presence of the ether linkage in Bis[2-(dicyclohexylphosphino)phenyl] ether enables the creation of materials with specific properties, such as enhanced thermal stability and mechanical strength. These materials are employed in various industries, including electronics, coatings, and composites.

Additionally, Bis[2-(dicyclohexylphosphino)phenyl] ether is valuable in the development of new chemical methodologies. Its unique structural features allow chemists to design and optimize novel synthetic routes and reaction conditions. The compound's ability to act as a chelating ligand enhances the versatility of metal catalysts, making it an important tool in research and industrial applications.

Handling and storage of Bis[2-(dicyclohexylphosphino)phenyl] ether require standard precautions due to its chemical reactivity. The compound should be stored in a dry, cool environment, away from moisture and air, to maintain its stability and effectiveness.

Future research on Bis[2-(dicyclohexylphosphino)phenyl] ether may focus on exploring new applications and optimizing its use in various catalytic and materials science contexts. Continued investigation into its properties and performance could lead to advancements in both synthetic methodologies and material development.

References

2015. Toward the development of efficient and stable Pd-catalysts for the methoxycarbonylation of medium chain alkenes. Journal of the Iranian Chemical Society, 12(6).
DOI: 10.1007/s13738-015-0750-5