tert-Butyldiphenylphosphine
[CAS# 6002-34-2]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: tert-Butyldiphenylphosphine
• Synonyms: Diphenyl-tert-butylphosphine; NSC 244302
• Molecular Formula: C₁₆H₁₉P
• Molecular Weight: 242.30
• CAS Registry Number: 6002-34-2
• EC Number: 227-848-6
• SMILES: CC(C)(C)P(C1=CC=CC=C1)C2=CC=CC=C2

Properties

• Solubility: Insoluble (9.0E^-4 g/L) (25 ºC), Calc.^*
• Boiling Point: 320.5±11.0 ºC (760 mmHg), Calc.^*
• Flash Point: 154.4±25.6 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Hazard Statements: H315-H317-H319-H335-H360
• Precautionary Statements: P201-P261-P280-P305+P351+P338-P308+P313

Discovory and Applicatios

tert-Butyldiphenylphosphine is a notable organophosphorus compound with significant applications in catalysis and organic synthesis. Discovered in the early 1980s, it was part of an initiative to explore organophosphorus compounds for their utility in chemical transformations. The synthesis of tert-butyldiphenylphosphine typically involves reacting tert-butyl chloride with diphenylphosphine under anhydrous conditions to prevent hydrolysis and ensure high yields of the desired product. The presence of the tert-butyl group imparts considerable steric bulk to the molecule, which plays a crucial role in its applications.

One of the primary uses of tert-butyldiphenylphosphine is as a ligand in organometallic chemistry. The bulky tert-butyl group around the phosphorus atom provides a unique environment for transition metal complexes, affecting their reactivity and selectivity. This steric influence is particularly valuable in catalytic processes, where precise control over the metal-ligand environment can lead to enhanced catalytic performance.

In hydrogenation reactions, tert-butyldiphenylphosphine is used to stabilize metal catalysts such as palladium and platinum. By coordinating with these metals, it facilitates the reduction of alkenes and alkynes, improving the efficiency and selectivity of the hydrogenation process. The compound's ability to create a sterically hindered environment around the metal center helps in controlling the reactivity and ensuring that the desired products are obtained with high purity.

Another significant application of tert-butyldiphenylphosphine is in cross-coupling reactions. In these reactions, it acts as a ligand to stabilize metal intermediates, particularly those involving palladium or nickel catalysts. The steric effects of the tert-butyl group influence the outcome of these reactions by modifying the coordination environment of the metal center. This adjustment can lead to increased yields and selectivity in the coupling process, making it a valuable tool for synthetic chemists.

Beyond its role in hydrogenation and cross-coupling reactions, tert-butyldiphenylphosphine is employed in the synthesis of complex organic molecules. Its ability to form stable complexes with transition metals is utilized in the preparation of various organometallic compounds and materials. The compound's steric properties can be leveraged to control the formation of specific isomers or products in multi-step synthetic routes, enhancing its versatility in organic synthesis.

Future research may further explore the potential applications of tert-butyldiphenylphosphine in new areas of chemical synthesis and materials science. By continuing to investigate its properties and reactivity, researchers could develop novel catalytic systems and synthetic methodologies. The ongoing exploration of this compound is expected to contribute to advancements in both academic and industrial chemistry.