2-Diphenylphosphino-2',6'-bis(dimethylamino)-1,1'-biphenyl
[CAS# 1447963-71-4]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: 2-Diphenylphosphino-2',6'-bis(dimethylamino)-1,1'-biphenyl
• Synonyms: 2-(2-diphenylphosphanylphenyl)-1-N,1-N,3-N,3-N-tetramethylbenzene-1,3-diamine
• Molecular Formula: C₂₈H₂₉N₂P
• Molecular Weight: 424.52
• CAS Registry Number: 1447963-71-4
• EC Number: 813-051-6
• SMILES: CN(C)C1=C(C(=CC=C1)N(C)C)C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4

Properties

• Boiling Point: 569.7±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 298.3±30.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315
• Precautionary Statements: P264-P280-P302+P352-P321-P332+P317-P362+P364

Discovory and Applicatios

2-Diphenylphosphino-2',6'-bis(dimethylamino)-1,1'-biphenyl is a notable organophosphorus compound recognized for its distinctive ligand structure and its valuable role in organometallic chemistry. This chemical is characterized by its biphenyl backbone, which is substituted with both diphenylphosphine and bis(dimethylamino) groups, imparting unique electronic and steric properties that are advantageous in various catalytic processes.

The discovery of 2-Diphenylphosphino-2',6'-bis(dimethylamino)-1,1'-biphenyl represents a significant advancement in the development of ligands for transition metal complexes. Its design aims to optimize the coordination environment around a metal center, enhancing both the stability and reactivity of the resulting complexes. The compound's unique structure enables it to engage effectively with transition metals, making it a versatile tool in catalysis.

The diphenylphosphine group in this compound provides strong donor properties, stabilizing metal centers through coordination. The bulky nature of the diphenyl substituents creates a significant steric environment, which is crucial for influencing the reactivity of the metal center and preventing catalyst deactivation. This steric bulk is particularly useful in promoting selectivity and enhancing the efficiency of catalytic reactions.

The bis(dimethylamino) substituents at the 2' and 6' positions of the biphenyl ring contribute to the ligand's electronic properties. These groups can engage in electron-donating interactions, further stabilizing the metal center and affecting the electronic environment around it. The combination of these electronic and steric effects enhances the performance of the metal complexes in various chemical transformations.

One of the primary applications of 2-Diphenylphosphino-2',6'-bis(dimethylamino)-1,1'-biphenyl is in the formation of transition metal complexes used in catalytic processes. It is especially useful in catalytic reactions that require precise control over the metal center's reactivity and selectivity. Examples include cross-coupling reactions, such as Suzuki-Miyaura or Negishi coupling, where the ligand's properties play a crucial role in achieving high yields and selectivity.

Additionally, the compound is explored for its role in other catalytic transformations, including oxidative and reduction reactions. Its ability to stabilize different oxidation states of the metal center makes it valuable for a range of processes in organic synthesis and materials science.

In summary, 2-Diphenylphosphino-2',6'-bis(dimethylamino)-1,1'-biphenyl is an advanced ligand with significant applications in organometallic chemistry. Its unique combination of steric and electronic effects provides valuable control over metal-centered catalytic processes, enhancing performance and selectivity in various chemical reactions.