9-[2-(Dicyclohexylphosphino)phenyl]-9H-carbazole
[CAS# 1308652-64-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: 9-[2-(Dicyclohexylphosphino)phenyl]-9H-carbazole
• Synonyms: (2-carbazol-9-ylphenyl)-dicyclohexylphosphane
• Molecular Formula: C₃₀H₃₄NP
• Molecular Weight: 439.57
• CAS Registry Number: 1308652-64-3
• SMILES: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3N4C5=CC=CC=C5C6=CC=CC=C64

Properties

• Melting point: 186-190 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335-H413
• Precautionary Statements: P261-P305+P351+P338-P273-P501

Discovory and Applicatios

9-[2-(Dicyclohexylphosphino)phenyl]-9H-carbazole is a versatile chemical compound notable for its role as a ligand in organometallic chemistry. This compound combines the structural features of carbazole with a dicyclohexylphosphino group, offering unique properties that are valuable in various chemical applications.

The discovery of 9-[2-(Dicyclohexylphosphino)phenyl]-9H-carbazole stems from ongoing research into phosphine-based ligands and their applications in catalysis. Carbazole, a nitrogen-containing heterocycle, is known for its stability and electronic properties, while the dicyclohexylphosphino group is recognized for its strong electron-donating ability. The combination of these two components in a single molecule enhances the ligand's ability to stabilize metal centers and influence their reactivity.

In terms of applications, 9-[2-(Dicyclohexylphosphino)phenyl]-9H-carbazole is primarily used as a ligand in transition metal catalysis. The presence of the dicyclohexylphosphino group provides excellent coordination to metal centers, such as palladium, platinum, and nickel, making it effective in various catalytic processes. These metals are often employed in cross-coupling reactions, including Suzuki and Heck reactions, where the ligand helps to facilitate the formation of carbon-carbon bonds.

The unique structure of 9-[2-(Dicyclohexylphosphino)phenyl]-9H-carbazole also imparts specific advantages in these catalytic reactions. The bulky dicyclohexyl groups enhance the steric profile of the ligand, which can help to prevent catalyst deactivation and improve the selectivity of the reactions. Additionally, the electronic properties of the carbazole unit contribute to the overall stability and reactivity of the metal-ligand complex.

Furthermore, this compound has applications beyond traditional catalysis. Its unique combination of electronic and steric properties makes it useful in the development of new materials, particularly in the field of organic electronics. The carbazole moiety, known for its electron-donating characteristics, can be advantageous in designing materials for organic light-emitting diodes (OLEDs) and other electronic devices.

In summary, 9-[2-(Dicyclohexylphosphino)phenyl]-9H-carbazole is a significant ligand in organometallic chemistry, offering valuable properties for catalytic and material science applications. Its ability to stabilize metal centers and influence reaction outcomes makes it a valuable tool in various chemical processes, while its unique structure provides additional benefits in the development of advanced materials.