1,6-Bis(diphenylphosphino)hexane
[CAS# 19845-69-3]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 1,6-Bis(diphenylphosphino)hexane
• Synonyms: 6-diphenylphosphanylhexyl(diphenyl)phosphane
• Molecular Formula: C₃₀H₃₂P₂
• Molecular Weight: 454.52
• CAS Registry Number: 19845-69-3
• EC Number: 626-555-4
• SMILES: C1=CC=C(C=C1)P(CCCCCCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4

Properties

• Melting point: 124-126 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

1,6-Bis(diphenylphosphino)hexane, also known as DPPH, is a versatile ligand used in various fields of organometallic chemistry and catalysis. This compound features two diphenylphosphino groups connected by a hexane chain, creating a bidentate ligand that binds to metal centers in a chelating fashion.

The discovery of 1,6-Bis(diphenylphosphino)hexane dates back to the early 1980s, when researchers were investigating new ligands for metal-catalyzed reactions. The hexane chain provides flexibility, while the diphenylphosphino groups offer strong donor properties, making it an ideal candidate for stabilizing metal complexes and facilitating catalytic processes.

One of the primary applications of 1,6-Bis(diphenylphosphino)hexane is in the field of homogeneous catalysis. The compound is commonly used as a ligand in palladium and nickel catalysts, where it helps to enhance the efficiency of cross-coupling reactions, such as the Suzuki and Heck reactions. These reactions are vital for the synthesis of complex organic molecules and materials, including pharmaceuticals and polymers.

The chelating nature of 1,6-Bis(diphenylphosphino)hexane allows it to form stable complexes with transition metals. These complexes are valuable for their ability to facilitate a range of chemical transformations, including oxidative additions, reductive eliminations, and C-C bond formations. The presence of the diphenylphosphino groups ensures strong metal-ligand interactions, which contribute to the high catalytic activity and selectivity of the resulting metal complexes.

In addition to its role in catalysis, 1,6-Bis(diphenylphosphino)hexane is used in the development of new materials. Its ability to form stable metal complexes makes it useful in the creation of functionalized materials with tailored properties. These materials can be employed in various applications, such as sensors, electronics, and energy storage devices.

The versatility and effectiveness of 1,6-Bis(diphenylphosphino)hexane in facilitating metal-catalyzed reactions have made it a valuable tool in both academic research and industrial processes. Its continued use and study contribute to advancements in the field of organometallic chemistry, highlighting its importance in the development of new catalytic methods and materials.

References

2024. Molecule-like synthesis of ligand-protected metal nanoclusters. *Nature Reviews Materials*.
DOI: 10.1038/s41578-024-00741-7

2023. Cobalt-Catalyzed C-C Coupling Reactions with Csp3 Electrophiles. *C-C Cross Couplings with 3d Base Metal Catalysts*.
DOI: 10.1007/3418_2023_83

2021. A Tetranuclear Propane-1,3-Dithiolate Complex, [Fe2(CO)5{Ph2P(CH2)3}{(µ-SCH2)2CH2}]2, with a Bridging 1,6-Bis(diphenylphosphino)hexane Ligand. *Journal of Chemical Crystallography*.
DOI: 10.1007/s10870-021-00910-4