Bis[4-(2-phenyl-2-propyl)phenyl]amine
[CAS# 10081-67-1]

Identification

• Classification: Pharmaceutical intermediate >> Diphenylamine intermediate
• Name: Bis[4-(2-phenyl-2-propyl)phenyl]amine
• Synonyms: Antioxidant 445; 4-(1-Methyl-1-phenylethyl)-N-[4-(1-methyl-1-phenylethyl)phenyl]aniline; 4-(1-Methyl-1-phenylethyl)-N-[4-(1-methyl-1-phenylethyl)phenyl]benzenamine
• Molecular Formula: C₃₀H₃₁N
• Molecular Weight: 405.58
• CAS Registry Number: 10081-67-1
• EC Number: 233-215-5
• SMILES: CC(C)(C1=CC=CC=C1)C2=CC=C(C=C2)NC3=CC=C(C=C3)C(C)(C)C4=CC=CC=C4

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 100 °C
• Index of Refraction: 1.607, Calc.^*
• Boiling Point: 535.2±39.0 °C (760 mmHg), Calc.^*
• Flash Point: 292.0±22.5 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H413
• Safety Statements: P261-P272-P273-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin sensitization	Skin Sens.	1B	H317
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Bis[4-(2-phenyl-2-propyl)phenyl]amine, also known as 4,4'-bis(2-phenyl-2-propyl)diphenylamine, is an organic compound that has garnered interest for its unique structural properties and potential applications in various fields, particularly in materials science and organic electronics. This compound is classified as a diphenylamine derivative, featuring two 4-(2-phenyl-2-propyl)phenyl groups attached to a central nitrogen atom.

The discovery of bis[4-(2-phenyl-2-propyl)phenyl]amine can be traced back to ongoing research into nitrogen-containing heterocycles and their derivatives, which have been investigated for their electronic and optical properties. The synthesis of this compound typically involves a multi-step chemical process, where starting materials undergo reactions such as Friedel-Crafts alkylation and subsequent coupling reactions to form the desired product. This synthetic pathway allows for the introduction of the phenyl groups, leading to a compound with intriguing electronic characteristics.

One of the most significant applications of bis[4-(2-phenyl-2-propyl)phenyl]amine lies in the field of organic electronics, particularly in organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs). The compound has been identified as a potential hole transport material due to its ability to facilitate the movement of positive charge carriers within these devices. Its high thermal stability and good solubility make it an attractive candidate for enhancing the performance and efficiency of OLEDs and OPVs, where effective charge transport is crucial for device functionality.

In addition to its use in organic electronics, bis[4-(2-phenyl-2-propyl)phenyl]amine has also been explored for its potential as a stabilizer in polymer systems. The compound can enhance the thermal and oxidative stability of various polymer materials, which is particularly important in applications where materials are exposed to harsh environmental conditions. By incorporating bis[4-(2-phenyl-2-propyl)phenyl]amine into polymer matrices, manufacturers can improve the longevity and performance of products in industries ranging from automotive to consumer goods.

Moreover, the unique structural properties of bis[4-(2-phenyl-2-propyl)phenyl]amine make it a valuable intermediate in the synthesis of other chemical compounds. Its reactivity and functional groups can be utilized to create new materials with tailored properties, further expanding its application potential in research and industrial settings.

Despite its promising applications, it is essential to consider the safety and environmental implications of bis[4-(2-phenyl-2-propyl)phenyl]amine. As with many organic compounds, exposure during synthesis or use may pose health risks, and regulatory guidelines must be followed to ensure safe handling. Ongoing research aims to better understand the compound's toxicological profile and to develop safer alternatives where possible.

In conclusion, bis[4-(2-phenyl-2-propyl)phenyl]amine is an important chemical compound with significant applications in organic electronics and polymer stabilization. Its discovery and subsequent utilization highlight the importance of nitrogen-containing compounds in advancing materials science. As research continues, bis[4-(2-phenyl-2-propyl)phenyl]amine may play a crucial role in the development of innovative materials and technologies.

References

1995. Photoinduced bimolecular cyclization of diarylamines and polyhalogenomethanes into acridines. Russian Chemical Bulletin, 44(2).
DOI: 10.1007/bf00702130

2016. Preparation and properties of the novel photoluminescent and thermosensitive hydrogels. Journal of Polymer Research, 23(5).
DOI: 10.1007/s10965-016-0986-5

2024. Acid Treatment on Bentonite Catalysts for Alkylation of Diphenylamine. Catalysis Letters, 154(9).
DOI: 10.1007/s10562-024-04697-9