2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
[CAS# 657408-07-6]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl
• Synonyms: Sphos
• Molecular Formula: C₂₆H₃₅O₂P
• Molecular Weight: 410.53
• CAS Registry Number: 657408-07-6
• EC Number: 613-838-2
• SMILES: COC1=C(C(=CC=C1)OC)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4

Properties

• Melting point: 164-166 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H317-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl, often abbreviated as DCyP-Biphenyl, is a sophisticated ligand that plays a crucial role in modern organometallic chemistry. This compound, characterized by its unique structure, has proven to be highly effective in facilitating various catalytic processes.

The discovery of DCyP-Biphenyl arose from the need for ligands with specific steric and electronic properties to enhance the performance of metal catalysts. The ligand features a biphenyl backbone with two methoxy groups at the 2' and 6' positions, along with two dicyclohexylphosphino groups. The combination of these features imparts both steric hindrance and electronic tuning to the ligand.

The primary application of DCyP-Biphenyl is in palladium-catalyzed cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. These reactions are fundamental in organic synthesis, enabling the formation of carbon-carbon bonds critical for constructing complex molecules. The presence of the dicyclohexylphosphino groups provides significant steric protection to the palladium center, which helps to stabilize the catalyst and prevent deactivation during the reaction. This results in improved efficiency and selectivity of the catalytic process.

The methoxy groups attached to the biphenyl backbone play a crucial role in modulating the electronic environment of the ligand. These groups influence the electronic properties of the ligand, thereby affecting the reactivity and stability of the palladium complex. This fine-tuning ability makes DCyP-Biphenyl particularly effective in a wide range of catalytic applications, including those involving challenging substrates.

DCyP-Biphenyl has also shown promise in other types of catalytic reactions, including carbonylation and C-H activation processes. Its versatility and adaptability stem from its ability to stabilize the metal center and optimize the reaction conditions. This makes it a valuable tool for chemists working on diverse synthetic challenges.

In summary, 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl exemplifies the advancements in ligand design that enhance catalytic efficiency and selectivity. Its unique combination of steric and electronic properties contributes to its effectiveness in palladium-catalyzed reactions and other catalytic processes. As research in catalytic chemistry continues to evolve, DCyP-Biphenyl remains an important compound for both academic research and industrial applications.

References

2023. Development of a Reproducible and Scalable Method for the Synthesis of Biologically Active Pyrazolo[1,5-a]pyrimidine Derivatives. Russian Journal of General Chemistry, 93(5).
DOI: 10.1134/s1070363223050043

2022. Recent Metal-Catalyzed Methods for Thioether Synthesis. Synthesis, 54(22).
DOI: 10.1055/a-1914-1231

2006. A Mixed Naphthyl-Phenyl Phosphine Ligand Motif for Suzuki, Heck, and Hydrodehalogenation Reactions. Synlett, 2006(18).
DOI: 10.1055/s-2006-951538