1,5-Bis(diphenylphosphino)pentane
[CAS# 27721-02-4]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 1,5-Bis(diphenylphosphino)pentane
• Synonyms: 5-diphenylphosphanylpentyl(diphenyl)phosphane
• Molecular Formula: C₂₉H₃₀P₂
• Molecular Weight: 440.50
• CAS Registry Number: 27721-02-4
• EC Number: 626-285-7
• SMILES: C1=CC=C(C=C1)P(CCCCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4

Properties

• Melting point: 42-47 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-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
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

1,5-Bis(diphenylphosphino)pentane is a prominent organophosphorus compound renowned for its role as a bidentate ligand in coordination chemistry and catalysis. Featuring two diphenylphosphino groups attached to a linear pentane backbone, this compound exemplifies the application of phosphine ligands in a variety of chemical transformations and catalytic processes.

The discovery of 1,5-Bis(diphenylphosphino)pentane arose from efforts to design new ligands with improved steric and electronic properties for transition metal coordination. The choice of a pentane linker, combined with the diphenylphosphino groups, was intended to provide a flexible yet effective ligand that could stabilize metal centers and influence reaction pathways. The linear structure of the pentane backbone offers a unique configuration compared to other bidentate ligands, contributing to its distinctive reactivity.

The synthesis of 1,5-Bis(diphenylphosphino)pentane involves several steps starting from the preparation of the diphenylphosphine intermediates and the linear pentane backbone. Initially, diphenylphosphine is synthesized or obtained from commercial sources. The next step involves the construction of the pentane backbone, typically achieved through the use of a suitable starting material that undergoes reaction with the diphenylphosphine under specific conditions. The resulting product is then purified by methods such as column chromatography or recrystallization to ensure high purity and yield.

1,5-Bis(diphenylphosphino)pentane is primarily used as a bidentate ligand in the coordination chemistry of transition metals. Its two diphenylphosphino groups can effectively coordinate with metal centers, forming stable chelate complexes. These complexes are valuable in various catalytic reactions, including cross-coupling reactions, hydrogenation, and oxidation. The ligand's ability to stabilize metal centers enhances the efficiency and selectivity of these catalytic processes.

One significant application of 1,5-Bis(diphenylphosphino)pentane is in the Suzuki-Miyaura coupling reaction, where it aids in the formation of carbon-carbon bonds between aryl halides and aryl boronic acids. The ligand’s steric and electronic properties contribute to the formation of highly active and selective palladium catalysts, which are crucial for the synthesis of complex organic molecules. Additionally, the compound is used in other metal-catalyzed reactions such as the Heck reaction and the olefin metathesis, where its unique structural features improve catalytic performance.

In addition to its catalytic applications, 1,5-Bis(diphenylphosphino)pentane finds use in the development of new materials. The ligand can be incorporated into metal-organic frameworks (MOFs) and other advanced materials, where it contributes to the materials' structural and electronic properties. These applications are important for developing new technologies in areas such as sensing, separation, and energy storage.

The advantages of using 1,5-Bis(diphenylphosphino)pentane include its ability to form stable chelate complexes with transition metals and its versatility in different catalytic processes. The linear pentane backbone provides a unique geometry that can influence the reactivity and selectivity of the metal-ligand complexes. However, challenges may include optimizing the synthesis and reaction conditions to achieve the desired performance and stability of the metal-ligand complexes.

Future research on 1,5-Bis(diphenylphosphino)pentane may explore its use in new catalytic applications, including asymmetric synthesis and other advanced chemical processes. Additionally, researchers may investigate modifications to the ligand’s structure to enhance its properties and expand its utility in material science and industrial applications.

References

1987. Antitumor activity of bis(diphenylphosphino)alkanes, their gold(I) coordination complexes, and related compounds. Journal of Medicinal Chemistry.
DOI: 10.1021/jm00395a004

2014. Carborane complexes of ruthenium with long-chain diphosphine ligands as effective catalysts of controlled radical polymerization. Polymer Science, Series B.
DOI: 10.1134/s1560090414010023

2012. Palladium-Catalyzed Carbonylative Dimerization of Styrenes to 1,5-Diarylpent-1-en-3-ones. Chemistry - An Asian Journal.
DOI: 10.1002/asia.201100836