Diphenyl-2-pyridylphosphine
[CAS# 37943-90-1]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Diphenyl-2-pyridylphosphine
• Molecular Formula: C₁₇H₁₄NP
• Molecular Weight: 263.28
• CAS Registry Number: 37943-90-1
• EC Number: 629-049-1
• SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=N3

Properties

• Melting point: 82-84 ºC

Safety Data

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

Hazard Classification

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

Discovory and Applicatios

Diphenyl-2-pyridylphosphine is a notable chemical compound in the realm of organophosphorus chemistry, recognized for its significant applications in catalysis and materials science. This compound features a phosphorus atom bonded to two phenyl groups and one pyridyl group, making it a versatile ligand in various chemical processes.

The discovery of diphenyl-2-pyridylphosphine stems from the broader investigation of phosphine ligands and their role in coordination chemistry. Phosphine ligands are crucial in facilitating a range of chemical reactions, particularly in transition metal catalysis. The introduction of the 2-pyridyl group into the diphenylphosphine framework was driven by the desire to enhance the ligand's electronic and steric properties, which can improve the performance of metal catalysts.

The synthesis of diphenyl-2-pyridylphosphine involves several steps. Initially, the 2-pyridylphosphine precursor is synthesized through a process that includes the reaction of a phosphine source with 2-pyridyl chloride. This reaction typically requires a suitable solvent and controlled temperature to ensure high yield and purity. The resulting product is then treated with phenyl groups, usually via a palladium-catalyzed coupling reaction, to form diphenyl-2-pyridylphosphine. Characterization of the compound is performed using techniques such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry to confirm its structure and purity.

Diphenyl-2-pyridylphosphine is primarily used as a ligand in coordination chemistry and catalysis. The compound's ability to form stable complexes with transition metals makes it valuable in a range of catalytic applications. One of the key uses of diphenyl-2-pyridylphosphine is in homogeneous catalysis, where it coordinates with metals such as palladium or platinum to facilitate various reactions. For instance, it is employed in cross-coupling reactions, including the Suzuki and Heck reactions, where it helps in the formation of carbon-carbon bonds. The ligand’s unique electronic properties, imparted by the pyridyl group, enhance the efficiency and selectivity of these reactions.

In addition to its role in cross-coupling reactions, diphenyl-2-pyridylphosphine is used in other catalytic processes such as hydrogenation and hydroformylation. The ligand's ability to stabilize metal centers and influence their reactivity makes it a valuable tool for developing new chemical transformations. Its versatility in coordinating with different metals and participating in various reactions underscores its importance in the field of organometallic chemistry.

Beyond catalysis, diphenyl-2-pyridylphosphine finds applications in materials science. The compound's electronic and steric properties can be utilized to design and synthesize new materials with specific characteristics. For example, it can be used to develop phosphine-based polymers or materials with tailored optical or electronic properties. These materials have potential applications in sensors, electronic devices, and other advanced technologies.

The use of diphenyl-2-pyridylphosphine also presents challenges. The synthesis of the compound requires careful control of reaction conditions and purification processes to achieve high yield and purity. Additionally, optimizing its performance in various catalytic reactions can involve extensive experimentation and fine-tuning of reaction parameters.

Future research on diphenyl-2-pyridylphosphine may focus on expanding its applications in emerging fields such as sustainable chemistry and green catalysis. The compound’s unique properties offer opportunities for developing more efficient and environmentally friendly chemical processes. Ongoing research may also explore new ways to functionalize or modify the ligand to enhance its performance in diverse chemical transformations.

References

2023. High efficiency warm-white light-emitting diodes based on copper-iodide clusters. Nature Photonics, 18(2).
DOI: 10.1038/s41566-023-01340-8

2023. Synthesis of non-equivalent diamides and amido-esters via Pd-catalysed carbonylation. Nature Synthesis, 3(2).
DOI: 10.1038/s44160-023-00411-6

2018. Hydride Induced Formation and Optical Properties of Tetrahedral [Cu4(μ4-H)(μ2-X)2(PPh2Py)4]+ Clusters (X = Cl, Br; Py = pyridyl). Journal of Cluster Science, 29(3).
DOI: 10.1007/s10876-018-1359-5