4-N-[4-[4-[[4-[4-[[4-(4-anilinophenyl)iminocyclohexa-2,5-dien-1-ylidene]amino]phenyl]iminocyclohexa-2,5-dien-1-ylidene]amino]anilino]phenyl]benzene-1,4-diamine
[CAS# 5612-44-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 4-N-[4-[4-[[4-[4-[[4-(4-anilinophenyl)iminocyclohexa-2,5-dien-1-ylidene]amino]phenyl]iminocyclohexa-2,5-dien-1-ylidene]amino]anilino]phenyl]benzene-1,4-diamine
• Synonyms: Polyaniline
• Molecular Formula: C₄₈H₃₈N₈
• Molecular Weight: 726.87
• CAS Registry Number: 5612-44-2
• SMILES: C1=CC=C(C=C1)NC2=CC=C(C=C2)N=C3C=CC(=NC4=CC=C(C=C4)N=C5C=CC(=NC6=CC=C(C=C6)NC7=CC=C(C=C7)NC8=CC=C(C=C8)N)C=C5)C=C3

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 869.2±65.0 ºC 760 mmHg (Calc.)^*
• Flash point: 479.5±34.3 ºC (Calc.)^*
• Index of refraction: 1.673 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

4-N-[4-[4-[[4-[4-[[4-(4-anilinophenyl)iminocyclohexa-2,5-dien-1-ylidene]amino]phenyl]iminocyclohexa-2,5-dien-1-ylidene]amino]anilino]phenyl]benzene-1,4-diamine is a highly conjugated organic compound belonging to the class of azo- and Schiff-base derivatives. Its molecular formula is C48H40N8. Structurally, it consists of multiple aromatic rings interconnected via imino (-C=NH-) linkages and substituted aniline groups, forming an extended system of alternating single and double bonds. This conjugation confers chromophoric properties, giving the compound a characteristic color and making it useful in dye chemistry.

The discovery and development of this type of molecule are tied to the field of organic dyes and colorimetric indicators. Extended conjugated systems with alternating imine and azo linkages are known for their strong absorption in the visible spectrum, enabling applications in textile dyeing, optical materials, and chemical sensors. The introduction of multiple aniline groups and imino linkages enhances electron delocalization, which can influence the color intensity and stability of the compound under light and heat.

Synthesis of this compound is generally carried out through stepwise condensation reactions between aromatic amines and cyclohexadienone derivatives to form Schiff bases. Each imino linkage is formed via a condensation reaction between a primary amine and a carbonyl group under mild acidic or neutral conditions. Careful control of stoichiometry, reaction temperature, and solvent polarity is required to avoid incomplete condensation or side reactions, and purification is typically performed using recrystallization or column chromatography to isolate the fully conjugated product.

Chemically, the compound exhibits properties characteristic of highly conjugated polyimines. The imino groups (-C=NH-) are electrophilic and can participate in further condensation or coordination reactions with metals. The extensive π-conjugation across the aromatic system results in strong absorption of visible light, making the compound chromophoric. It is also capable of forming hydrogen bonds through the aniline and imine functionalities, which can influence solubility, aggregation, and intermolecular interactions in solution or in solid-state assemblies.

In practical applications, compounds of this type are primarily used as dyes, pigments, or colorimetric reagents. Their vivid coloration and ability to undergo reversible chemical transformations make them suitable for applications in textile and polymer industries, as pH indicators, or in sensor devices where changes in color report on chemical or environmental changes. The extended conjugation can also be explored in organic electronics, such as in organic semiconductors or light-absorbing materials.

From a physical standpoint, the compound is generally a solid at room temperature with low solubility in water but good solubility in polar organic solvents such as ethanol, dimethylformamide, or chloroform. It is sensitive to strong acids, bases, or oxidizing agents that can hydrolyze imino linkages or disrupt conjugation. Handling precautions include using gloves, eye protection, and adequate ventilation to avoid irritation or inhalation of dust.

Overall, 4-N-[4-[4-[[4-[4-[[4-(4-anilinophenyl)iminocyclohexa-2,5-dien-1-ylidene]amino]phenyl]iminocyclohexa-2,5-dien-1-ylidene]amino]anilino]phenyl]benzene-1,4-diamine is a highly conjugated Schiff-base derivative with notable chromophoric properties. Its extensive π-conjugation, multiple aromatic rings, and imino linkages make it a valuable compound for dye chemistry, colorimetric analysis, and materials science. The molecule exemplifies the use of extended conjugated systems in applications requiring strong light absorption, color stability, and tunable electronic properties.

References

2021. A kind of preparation method of ionic liquid modified polyaniline/titanium dioxide composite material. CN Patent.
URL: CN-108479857-B

2020. Polyaniline/titanium dioxide composite material and application thereof in environmental remediation. CN Patent.
URL: CN-108554459-B