Bis(4-tolyl)phosphine
[CAS# 1017-60-3]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Bis(4-tolyl)phosphine
• Synonyms: Bis(p-methylphenyl)phosphine; Di-p-tolylphosphine
• Molecular Formula: C₁₄H₁₅P
• Molecular Weight: 214.24
• CAS Registry Number: 1017-60-3
• SMILES: CC1=CC=C(C=C1)PC2=CC=C(C=C2)C

Properties

• Boiling Point: 305.8±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 138.8±25.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS06;GHS07 Danger
• Hazard Statements: H250-H252-H301+H311-H332
• Precautionary Statements: P231-P301+P310-P305+P351+P338-P403+P233-P422-P501

Discovory and Applicatios

Bis(4-tolyl)phosphine is an organophosphorus compound widely recognized for its importance in catalysis and organic synthesis. The substance is characterized by the presence of two 4-tolyl groups (methyl-substituted phenyl groups) attached to a central phosphorus atom. This structural configuration gives bis(4-tolyl)phosphine unique chemical properties that make it an essential ligand in various catalytic processes, particularly in the field of transition metal catalysis.

The discovery of bis(4-tolyl)phosphine dates back to the ongoing research in the mid-20th century focused on the development of organophosphorus compounds. These compounds were of particular interest due to their ability to coordinate with metal centers and influence the reactivity and selectivity of metal-catalyzed reactions. Bis(4-tolyl)phosphine, with its relatively simple yet effective structure, quickly became a subject of study for chemists exploring its potential as a ligand.

One of the primary applications of bis(4-tolyl)phosphine is its role as a ligand in transition metal catalysis. In these catalytic systems, the ligand is crucial for stabilizing the metal center, modulating its electronic properties, and thus influencing the outcome of the catalytic reaction. Bis(4-tolyl)phosphine has been shown to form stable complexes with a variety of transition metals, including palladium, platinum, and rhodium. These complexes are widely used in cross-coupling reactions, such as Suzuki-Miyaura, Heck, and Stille couplings. These reactions are fundamental in organic synthesis, enabling the formation of carbon-carbon bonds that are essential in the construction of complex organic molecules, including pharmaceuticals, agrochemicals, and materials.

In addition to its catalytic applications, bis(4-tolyl)phosphine is also used as a reagent in the synthesis of other organophosphorus compounds. Its ability to undergo various chemical transformations allows it to serve as a building block in the preparation of more complex phosphine ligands, which are tailored for specific catalytic purposes. The versatility of bis(4-tolyl)phosphine in ligand design has made it a valuable tool in the development of new catalytic systems with improved efficiency, selectivity, and stability.

Moreover, the unique electronic and steric properties of bis(4-tolyl)phosphine have also been exploited in materials science. The phosphine's ability to coordinate with metal centers has been utilized in the design of coordination polymers and metal-organic frameworks (MOFs). These materials have a wide range of applications, from gas storage and separation to catalysis and drug delivery. The tunability of bis(4-tolyl)phosphine through modification of the tolyl groups further enhances its utility in these advanced materials, allowing researchers to fine-tune the properties of the resulting materials for specific applications.

The impact of bis(4-tolyl)phosphine on modern chemistry is significant, as it continues to be a critical component in both fundamental research and industrial processes. Its role as a ligand in catalysis has contributed to the development of more sustainable and efficient synthetic methods, while its applications in materials science have opened new avenues for the design of advanced materials with tailored properties.