4-(Dimethylamino)phenyldiphenylphosphine
[CAS# 739-58-2]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 4-(Dimethylamino)phenyldiphenylphosphine
• Synonyms: 4-(Diphenylphosphanyl)-N,N-dimethylaniline
• Molecular Formula: C₂₀H₂₀NP
• Molecular Weight: 305.35
• CAS Registry Number: 739-58-2
• EC Number: 626-713-2
• SMILES: CN(C)C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3

Properties

• Melting point: 151-154 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary 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
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

4-(Dimethylamino)phenyldiphenylphosphine is an organophosphorus compound with notable significance in various areas of chemical research and application. This chemical substance combines a diphenylphosphine group with a 4-(dimethylamino)phenyl substituent, providing unique steric and electronic properties that enhance its utility in multiple domains of chemistry.

The discovery of 4-(Dimethylamino)phenyldiphenylphosphine dates back to the early exploration of phosphorus-based ligands in coordination chemistry. Its synthesis typically involves the reaction of diphenylphosphine with 4-(dimethylamino)iodobenzene. This reaction requires careful control of conditions to ensure the successful formation of the phosphine ligand, which features the dimethylamino group ortho to the phosphine center. This substitution pattern influences the electronic properties of the ligand, making it an interesting subject for further study.

In terms of applications, 4-(Dimethylamino)phenyldiphenylphosphine plays a significant role as a ligand in coordination chemistry. The phosphine group is known for its ability to form stable complexes with transition metals. These metal-phosphine complexes are crucial in catalysis, particularly in processes such as cross-coupling reactions and asymmetric synthesis. The presence of the dimethylamino group enhances the ligand’s ability to stabilize metal centers and modulate their reactivity. This feature is particularly valuable in designing catalysts for selective transformations in organic synthesis.

One of the key applications of 4-(Dimethylamino)phenyldiphenylphosphine is in the development of homogeneous catalytic systems. The ligand's ability to coordinate with various transition metals, such as palladium and platinum, enables its use in catalytic cycles for reactions like Heck coupling, Suzuki-Miyaura coupling, and other carbon-carbon bond formation processes. The dimethylamino group contributes to the electronic tuning of the metal center, allowing for improved control over the reaction outcomes and efficiency.

Another important application of this ligand is in the field of organometallic chemistry, where it is used to prepare metal complexes with specific properties. These complexes can be utilized in materials science, particularly in the development of advanced materials with tailored electronic or optical properties. For instance, metal-phosphine complexes incorporating 4-(Dimethylamino)phenyldiphenylphosphine may be employed in the creation of new organic semiconductors or as components in molecular electronics.

In addition to its applications in catalysis and materials science, 4-(Dimethylamino)phenyldiphenylphosphine is also of interest in medicinal chemistry. The ligand's ability to form stable complexes with metal centers can be leveraged to explore new therapeutic agents or drug delivery systems. The electronic properties imparted by the dimethylamino group may influence the interaction of the metal complexes with biological targets, potentially leading to new insights and applications in drug development.

Overall, the discovery and utilization of 4-(Dimethylamino)phenyldiphenylphosphine highlight its versatility and importance in modern chemical research. Its unique structure and properties make it a valuable tool for chemists working in various fields, from catalysis to materials science and medicinal chemistry.

References

2018. Synthesis, spectroscopy and crystal structures of three diiron ethanedithiolate complexes with tertiary phosphine ligands: vinyldiphenylphosphine, 4-(dimethylamino)phenylphosphine or bis(4-methoxyphenyl)phenylphosphine. Transition Metal Chemistry, 43(7).
DOI: 10.1007/s11243-018-0263-z

2010. trans-Dichloridobis{[4-(dimethylamino)phenyl]diphenylphosphane}palladium(II). Acta Crystallographica. Section E, Structure Reports Online, 66(11).
DOI: 10.1107/s1600536810042595

2003. [4-(N,N-Dimethylamino)phenyl]diphenylphosphine Oxide and its Partial Oxides: An Isomorphous Crystal Series. Australian Journal of Chemistry, 56(11).
DOI: 10.1071/ch03089