2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl
[CAS# 213697-53-1]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl
• Synonyms: 2-(2-dicyclohexylphosphanylphenyl)-N,N-dimethylaniline
• Molecular Formula: C₂₆H₃₆NP
• Molecular Weight: 393.55
• CAS Registry Number: 213697-53-1
• EC Number: 606-749-5
• SMILES: CN(C)C1=CC=CC=C1C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4

Properties

• Melting point: 116-121 °C
• Water solubility: Insoluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-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
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl is a noteworthy chemical compound in the field of organophosphorus chemistry and catalysis. This compound features a biphenyl core with a dicyclohexylphosphino group and an N,N-dimethylamino group attached to the biphenyl structure, creating a molecule with unique electronic and steric properties.

The discovery of 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl emerged from the exploration of ligand systems used to enhance the performance of catalytic processes. The synthesis of this compound typically involves the reaction of dicyclohexylphosphine with 2'-bromo-N,N-dimethylaminobiphenyl. The resulting product features a phosphine group and an amine group, which contribute to the compound's functionality as a ligand in various chemical reactions.

One of the primary applications of 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl is in the field of catalysis. The compound acts as a ligand in transition metal-catalyzed reactions, where it plays a crucial role in stabilizing the metal center and influencing the reaction's selectivity and efficiency. For instance, in palladium-catalyzed cross-coupling reactions, this ligand can enhance the reaction's rate and yield, making it a valuable tool for synthesizing complex organic molecules.

The compound's unique structure allows it to coordinate effectively with transition metals, forming stable complexes that are essential for catalytic activity. The dicyclohexylphosphino group provides strong coordination to the metal center, while the N,N-dimethylamino group can influence the electronic properties of the ligand, affecting the overall reactivity and selectivity of the catalyst.

In addition to its role in catalysis, 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl is used in the development of new catalytic systems and materials. Researchers explore its properties to design ligands with improved performance for specific reactions, contributing to advancements in organic synthesis and materials science.

The study of 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl also enhances the understanding of ligand behavior in coordination chemistry. By examining the interactions between this ligand and various metal centers, scientists can gain insights into the design of more efficient and selective catalysts.

In summary, 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl is a valuable compound in organophosphorus chemistry, with significant applications in catalysis and materials development. Its unique properties make it an important tool for advancing chemical reactions and designing new catalytic systems.

References

2006. Urea as ammonia equivalent in aryl halides amination catalyzed by palladium complexes. Russian Journal of Organic Chemistry, 42(11).
DOI: 10.1134/s1070428006110133

2017. Recent Progress in the Cross-Coupling Reaction Using Triorganosilyl-Type Reagents. Synlett.
DOI: 10.1055/s-0036-1589008

2016. Synthesis from Imines and Haloalkenes by One-Pot Cross Coupling. Science of Synthesis.
URL: SD-115-00082