Diphenylphosphine
[CAS# 829-85-6]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Diphenylphosphine
• Molecular Formula: C₁₂H₁₁P
• Molecular Weight: 186.19
• CAS Registry Number: 829-85-6
• EC Number: 212-591-4
• SMILES: C1=CC=C(C=C1)PC2=CC=CC=C2

Properties

• Density: 1.07
• Boiling point: 280 °C
• Refractive index: 1.6260-1.6290
• Flash point: 110 °C

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H250-H315-H319-H335
• Safety Statements: P210-P222-P231-P233-P261-P264-P264+P265-P271-P280-P302+P335+P334-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Pyrophoric liquids	Pyr. Liq.	1	H250
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 2845

Discovery and Applications

Diphenylphosphine, a versatile organophosphorus compound, has made significant contributions to the field of chemistry since its discovery. Its unique structure, characterized by a central phosphorus atom bonded to two phenyl groups, imparts distinct chemical and physical properties that make it valuable in various chemical processes.

The synthesis of diphenylphosphine typically involves the reaction of phenylmagnesium bromide with phosphorus trichloride, resulting in the formation of this organophosphorus compound. The reaction is carried out under anhydrous conditions to prevent hydrolysis of the phosphorus trichloride, ensuring the successful formation of diphenylphosphine.

The discovery of diphenylphosphine marked a significant advancement in the development of phosphine ligands for transition metal chemistry. Its structure provides a balance of steric and electronic effects that are crucial for stabilizing metal centers in a variety of catalytic applications. The compound's ability to act as a bidentate ligand, where both phenyl groups coordinate to a metal center, enhances its effectiveness in stabilizing metal-ligand complexes.

In terms of applications, diphenylphosphine is extensively used in transition metal catalysis. It serves as a ligand in various catalytic reactions, including hydrogenation, cross-coupling, and hydroformylation. Its ability to stabilize metal centers makes it particularly useful in facilitating these reactions by providing electronic and steric support to the metal catalyst.

Diphenylphosphine is also employed in the synthesis of complex organic molecules. The compound's role as a ligand allows for the formation of metal complexes that act as intermediates in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. The versatility of diphenylphosphine in coordinating with different metals and its ability to influence the reactivity of metal centers make it a valuable tool in organic synthesis.

Beyond its applications in catalysis and synthesis, diphenylphosphine has been explored for its potential uses in material science. Its ability to stabilize metal centers can be harnessed to develop materials with specific properties, such as improved mechanical or electrical characteristics.

Overall, diphenylphosphine represents an important advancement in the field of organophosphorus chemistry. Its discovery and applications underscore the significance of phosphine ligands in enhancing the stability and reactivity of metal complexes, making it a crucial component in both industrial and academic research.

References

2024. Synthesis of functionalized 2-diphenylphosphinoethyl-containing phosphonous and phosphinic acids. Russian Chemical Bulletin, 73(2).
DOI: 10.1007/s11172-024-4145-6

2023. Chiral phosphoric acid-catalyzed enantioselective phosphinylation of 3,4-dihydroisoquinolines with diarylphosphine oxides. Communications Chemistry, 6(1).
DOI: 10.1038/s42004-023-00826-4

2023. Nucleophilic reactions of molybdenum cationic propargyl complexes. Russian Chemical Bulletin, 72(5).
DOI: 10.1007/s11172-023-3882-2