2-(Dicyclohexylphosphino)biphenyl
[CAS# 247940-06-3]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 2-(Dicyclohexylphosphino)biphenyl
• Synonyms: dicyclohexyl-(2-phenylphenyl)phosphane
• Molecular Formula: C₂₄H₃₁P
• Molecular Weight: 350.48
• CAS Registry Number: 247940-06-3
• EC Number: 607-439-2
• SMILES: C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4

Properties

• Melting point: 102-106 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335-H413
• Precautionary Statements: P261-P264-P264+P265-P271-P273-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
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

2-(Dicyclohexylphosphino)biphenyl is a prominent chemical compound known for its role as a ligand in transition metal catalysis. This compound, often abbreviated as DCP-BIPY, has gained considerable attention due to its effectiveness in facilitating various catalytic reactions, making it a valuable tool in both research and industrial applications.

The discovery of 2-(Dicyclohexylphosphino)biphenyl emerged in the late 20th century as part of a broader effort to develop new ligands that could offer enhanced performance in catalysis. The ligand features a biphenyl backbone with a dicyclohexylphosphino group attached to one of the biphenyl rings. This structure was designed to provide both steric protection and electronic effects that can significantly influence the behavior of metal catalysts.

The synthesis of 2-(Dicyclohexylphosphino)biphenyl involves several key steps. The process begins with the preparation of the biphenyl framework, which is typically achieved through coupling reactions of phenyl-containing precursors. The dicyclohexylphosphino group is then introduced to the biphenyl core via a reaction with a phosphorus-containing reagent. The resulting compound is purified through standard techniques such as column chromatography or recrystallization to obtain high-purity material for use in catalytic processes.

One of the primary applications of 2-(Dicyclohexylphosphino)biphenyl is in asymmetric catalysis. The ligand is used to create chiral metal complexes that can catalyze various asymmetric reactions, including hydrogenation, hydroformylation, and cross-coupling reactions. The dicyclohexylphosphino group provides significant steric hindrance, which can help stabilize transition states and influence the selectivity of the reactions. This feature is particularly valuable in asymmetric synthesis, where control over stereochemistry is crucial.

In hydrogenation reactions, 2-(Dicyclohexylphosphino)biphenyl is employed to create catalysts that enable the reduction of unsaturated compounds with high selectivity for specific products. The steric effects of the dicyclohexyl groups can enhance the catalytic efficiency and control the formation of the desired enantiomers.

The compound is also used in hydroformylation reactions, where it helps in the formation of aldehydes from alkenes. The presence of the dicyclohexylphosphino ligand can affect the reaction rate and selectivity, allowing for the production of aldehydes with high precision.

In cross-coupling reactions, 2-(Dicyclohexylphosphino)biphenyl serves as a ligand that facilitates the formation of carbon-carbon bonds. The unique steric and electronic properties imparted by the ligand contribute to improved yields and selectivity in the synthesis of complex organic molecules.

The advantages of using 2-(Dicyclohexylphosphino)biphenyl include its ability to provide a highly sterically demanding environment around the metal center, which can enhance catalytic performance. However, challenges associated with its use may include the need for careful optimization of reaction conditions to achieve the desired results and the potential for ligand deactivation in certain scenarios.

Future research into 2-(Dicyclohexylphosphino)biphenyl may focus on exploring new catalytic applications and optimizing the ligand’s performance in existing processes. Researchers may also investigate modifications to the ligand structure to further enhance its properties or develop new derivatives with improved reactivity and selectivity.

References

2022. Light-Driven Palladium-Radical Hybrid Species: Mechanistic Aspects and Recent Examples. *Synthesis*, 54(17).
DOI: 10.1055/a-1898-1816

2017. Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects. *Nature Chemistry*, 9(7).
DOI: 10.1038/nchem.2741

2003. Palladium Charcoal-Catalyzed Suzuki-Miyaura Coupling to Obtain Arylpyridines and Arylquinolines. *The Journal of Organic Chemistry*, 68(22).
DOI: 10.1021/jo034642