Di-t-butyl(n-butyl)phosphine
[CAS# 29949-72-2]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Di-t-butyl(n-butyl)phosphine
• Synonyms: butyl(ditert-butyl)phosphane
• Molecular Formula: C₁₂H₂₇P
• Molecular Weight: 202.32
• CAS Registry Number: 29949-72-2
• SMILES: CCCCP(C(C)(C)C)C(C)(C)C

Properties

• Boiling Point: 238.1±9.0 ºC (760 mmHg), Calc.^*
• Flash Point: 100.4±25.0 ºC, Calc.^*

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

Discovory and Applicatios

Di-t-butyl(n-butyl)phosphine is a significant chemical compound used primarily as a ligand in organometallic chemistry. This substance is characterized by the presence of two tert-butyl groups and one n-butyl group attached to a phosphorus atom. Its unique structure makes it valuable for stabilizing transition metals in various catalytic reactions.

The discovery of Di-t-butyl(n-butyl)phosphine was driven by the need for ligands that could provide enhanced stability and reactivity in metal-catalyzed processes. The tert-butyl groups offer steric protection, preventing the coordination of other unwanted ligands, while the n-butyl group contributes to the ligand’s flexibility and solubility in different solvents.

One of the key applications of Di-t-butyl(n-butyl)phosphine is in the field of catalysis, particularly in reactions involving transition metals such as palladium, platinum, and rhodium. This ligand is used in various catalytic processes, including cross-coupling reactions like the Suzuki and Heck reactions. These reactions are crucial for forming carbon-carbon bonds, which are essential for the synthesis of complex organic molecules used in pharmaceuticals, materials science, and other chemical industries.

In addition to cross-coupling reactions, Di-t-butyl(n-butyl)phosphine is also employed in hydrogenation and hydroformylation reactions. The ligand's ability to stabilize metal centers makes it effective in these transformations, which are important for producing a range of chemical products, including fine chemicals and intermediates in drug synthesis.

The stability and reactivity imparted by Di-t-butyl(n-butyl)phosphine have made it a valuable tool in both research and industrial applications. Its development has expanded the possibilities for efficient and selective metal-catalyzed reactions, facilitating advancements in synthetic chemistry and materials science.

Overall, Di-t-butyl(n-butyl)phosphine is an important ligand in organometallic chemistry, known for its role in enhancing the stability and effectiveness of metal catalysts in various chemical processes. Its contributions to catalysis underscore its significance in the development of advanced chemical synthesis techniques.