2-Aminodiphenylamine
[CAS# 534-85-0]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: 2-Aminodiphenylamine
• Synonyms: N-Phenyl-o-phenylenediamine
• Molecular Formula: C₁₂H₁₂N₂
• Molecular Weight: 184.24
• CAS Registry Number: 534-85-0
• EC Number: 208-606-9
• SMILES: C1=CC=C(C=C1)NC2=CC=CC=C2N

Properties

• Melting point: 77-82 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H332
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319
Germ cell mutagenicity	Muta.	2	H341

Discovory and Applicatios

2-Aminodiphenylamine is a notable chemical compound with applications in various fields of organic synthesis and materials science. As an organic compound with the formula C₁₂H₁₁N, 2-Aminodiphenylamine features an amino group attached to a diphenylamine structure. Its discovery and subsequent applications highlight its role as a versatile building block in both chemical synthesis and material development.

The synthesis of 2-Aminodiphenylamine typically involves the introduction of an amino group to the diphenylamine framework. This process can be achieved through several synthetic routes, including the reduction of nitro derivatives or the direct amination of diphenylamine. The choice of method depends on the desired purity and yield, as well as the specific application for which the compound is intended.

Structurally, 2-Aminodiphenylamine consists of a central diphenylamine moiety with an amino group positioned on one of the phenyl rings. This configuration imparts unique electronic and steric properties to the molecule, making it a useful intermediate in the synthesis of various functional materials and chemical products.

One of the primary applications of 2-Aminodiphenylamine is in the synthesis of dyes and pigments. The compound can serve as a precursor for the development of azo dyes and other colored compounds used in textile and polymer industries. The amino group in 2-Aminodiphenylamine can be involved in various reactions to form dye structures that exhibit vibrant colors and good stability, which are essential for industrial applications.

In addition to its role in dye synthesis, 2-Aminodiphenylamine is utilized in the development of organic semiconductors. The compound's electronic properties allow it to function as a building block in the creation of organic light-emitting diodes (OLEDs) and organic photovoltaic cells (OPVs). Its ability to influence charge transport and energy levels in these materials makes it a valuable component in advancing organic electronic technologies.

2-Aminodiphenylamine is also employed in the synthesis of pharmaceuticals and agrochemicals. The compound's amino group enables it to participate in various chemical reactions, leading to the formation of biologically active molecules. For example, it can be used in the synthesis of anti-inflammatory and antitumor agents, contributing to the development of new therapeutic compounds.

In materials science, 2-Aminodiphenylamine is used in the production of polymers and resins. The compound's reactivity allows it to be incorporated into polymer chains, influencing the properties of the resulting materials. This application is significant for the development of advanced materials with tailored properties for specific industrial applications.

Proper handling and storage of 2-Aminodiphenylamine are essential to maintain its stability and efficacy. The compound should be stored in a cool, dry place, away from light and moisture, to prevent degradation. Safety precautions should be observed during its handling to avoid exposure to the compound in its pure form.

Future research on 2-Aminodiphenylamine may focus on exploring its potential in new applications and improving its synthesis. Advances in understanding its chemical reactivity and interactions with other substances could lead to the development of innovative materials and products with enhanced performance characteristics.

References

2023. Design, synthesis, and antifungal activity of nicotinamide derivatives containing diphenylamine moieties. Journal of Chemical Sciences, 135(3).
DOI: 10.1007/s12039-022-02081-x

2011. Synthesis and biological activity of novel 4- and 6-(1-alkyl/aryl-1H-benzimidazol-2-yl)benzene-1,3-diols. Monatshefte für Chemie - Chemical Monthly, 142(12).
DOI: 10.1007/s00706-011-0665-5