N-[3-(Phenylamino)-2-propenylidene]benzenamine hydrochloride
[CAS# 50328-50-2]

Identification

• Name: N-[3-(Phenylamino)-2-propenylidene]benzenamine hydrochloride
• Synonyms: N-[(E)-3-phenyliminoprop-1-enyl]aniline;hydrochloride
• Molecular Formula: C₁₅H₁₅ClN₂
• Molecular Weight: 258.75
• CAS Registry Number: 50328-50-2
• EC Number: 256-545-1
• SMILES: C1=CC=C(C=C1)N/C=C/C=NC2=CC=CC=C2.Cl

Properties

• Melting point: 111-113 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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

N-[3-(Phenylamino)-2-propenylidene]benzenamine hydrochloride is an organic compound that has attracted attention due to its unique structure and potential applications in various fields, particularly in organic synthesis and materials science. This compound features a Schiff base, which is formed by the condensation of an amine with an aldehyde or ketone. The presence of a hydrochloride salt enhances its stability and solubility, making it more suitable for various applications.

The discovery of N-[3-(Phenylamino)-2-propenylidene]benzenamine hydrochloride is tied to the broader exploration of Schiff bases, a class of compounds first identified in the 19th century by Hugo Schiff. These compounds are known for their ability to form stable complexes with metals and for their utility in the synthesis of a wide range of organic molecules. The particular structure of N-[3-(Phenylamino)-2-propenylidene]benzenamine hydrochloride, with its conjugated double bonds and aromatic rings, gives it distinctive chemical properties that have been leveraged in various scientific and industrial applications.

One of the primary applications of N-[3-(Phenylamino)-2-propenylidene]benzenamine hydrochloride is in organic synthesis, where it serves as an important intermediate. Its Schiff base structure allows it to participate in a variety of chemical reactions, including cycloaddition and condensation reactions, which are key steps in the synthesis of more complex organic molecules. This makes it valuable in the development of pharmaceuticals, agrochemicals, and dyes. The presence of both phenylamine groups in the molecule provides opportunities for further functionalization, enabling chemists to modify the compound for specific purposes.

In pharmaceutical research, Schiff bases like N-[3-(Phenylamino)-2-propenylidene]benzenamine hydrochloride are investigated for their potential biological activities. Schiff bases are known to exhibit a range of pharmacological properties, including antimicrobial, antifungal, and anticancer activities. This has led to studies on this compound as a potential lead molecule for the development of new drugs. The ability of Schiff bases to coordinate with metal ions further enhances their utility in medicinal chemistry, as these metal complexes can exhibit enhanced biological activity compared to the free ligand.

Additionally, N-[3-(Phenylamino)-2-propenylidene]benzenamine hydrochloride is used in materials science, particularly in the development of organic electronic materials. Its conjugated structure, which allows for electron delocalization across the molecule, makes it a candidate for use in organic semiconductors and conductive polymers. These materials are essential components in the fabrication of organic light-emitting diodes (OLEDs), organic photovoltaic cells, and other electronic devices. The ability to fine-tune the electronic properties of the compound through chemical modifications further extends its applicability in these advanced technologies.

Moreover, this compound has potential applications in analytical chemistry as a reagent for detecting and quantifying metal ions. The Schiff base structure can selectively bind to certain metal ions, leading to color changes or other detectable signals, which can be used in the development of sensors or analytical methods for environmental monitoring and industrial processes.

In summary, N-[3-(Phenylamino)-2-propenylidene]benzenamine hydrochloride is a versatile compound with significant applications in organic synthesis, pharmaceutical research, materials science, and analytical chemistry. Its discovery and development as a Schiff base derivative have opened up new possibilities for the design of complex molecules and advanced materials, making it an important tool in both scientific research and industrial applications.