2'-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl[1,1'-biphenyl]-2,6-diamine
[CAS# 1160556-64-8]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: 2'-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl[1,1'-biphenyl]-2,6-diamine
• Synonyms: 2-(2-dicyclohexylphosphanylphenyl)-1-N,1-N,3-N,3-N-tetramethylbenzene-1,3-diamine
• Molecular Formula: C₂₈H₄₁N₂P
• Molecular Weight: 436.61
• CAS Registry Number: 1160556-64-8
• EC Number: 802-341-8
• SMILES: CN(C)C1=C(C(=CC=C1)N(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4

Properties

• Solubility: Insoluble (1.3E^-4 g/L) (25 °C), Calc.^*
• Melting point: 111-113 °C (dichloromethane methanol )^**

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

^** Han, Chong

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
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

2'-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl[1,1'-biphenyl]-2,6-diamine is a complex chemical compound that has garnered attention for its unique structure and versatile applications, particularly in the field of catalysis. This compound features a biphenyl core, which is a structure consisting of two connected benzene rings, modified with a dicyclohexylphosphino group and four methyl-substituted amine groups.

The discovery of 2'-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl[1,1'-biphenyl]-2,6-diamine is rooted in the need to develop new ligands that can effectively coordinate with transition metals in catalytic processes. The dicyclohexylphosphino group is a bulky, electron-rich phosphine that, when combined with the biphenyl core and the amine groups, creates a ligand with unique electronic and steric properties. These characteristics make it particularly useful in facilitating a wide range of chemical reactions, especially those involving transition metals.

One of the primary applications of this compound is in homogeneous catalysis, where it acts as a ligand to stabilize metal catalysts. In these reactions, the compound’s structure helps to enhance the reactivity and selectivity of the metal center, making it an important tool in the synthesis of complex organic molecules. It has been used in processes such as cross-coupling reactions, which are vital in the formation of carbon-carbon bonds, a key step in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals.

In addition to its role in catalysis, 2'-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl[1,1'-biphenyl]-2,6-diamine is also of interest in the development of new materials. The compound’s ability to coordinate with metals and influence their electronic properties can be exploited in the creation of novel materials with tailored properties, such as improved conductivity, stability, or catalytic activity.

The compound's structure also makes it a valuable subject of study in academic research. Understanding how the different functional groups interact with each other and with metal centers can provide insights into the design of more efficient and selective catalysts. Researchers continue to explore the potential modifications of this molecule to enhance its properties and broaden its applications.

In summary, 2'-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl[1,1'-biphenyl]-2,6-diamine is a compound of significant interest due to its unique structure and versatile applications in catalysis and material science. Its role as a ligand in transition metal-catalyzed reactions highlights its importance in advancing chemical synthesis and the development of new materials.

References

2018. Retaining Alkyl alkylated Nucleophile Regiofidelity in Transition-Metal-Mediated Reactions to Aryl Electrophiles. Synthesis.
DOI: 10.1055/s-0037-1609941

2016. Secondary Alkyl Halides in Palladium-Catalyzed Reactions. Synthesis.
DOI: 10.1055/s-0035-1561625

2014. Metal-Catalyzed Reactions in the Synthesis and Modification of Pyridines. Synthesis and Modification.
DOI: 10.1007/7081_2014_05