4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline
[CAS 13080-86-9]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Anilines
• Name: 4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline
• Synonyms: 2,2-Bis[4-(4-aminophenoxy)phenyl]propane
• Molecular Formula: C₂₇H₂₆N₂O₂
• Molecular Weight: 410.51
• CAS Registry Number: 13080-86-9
• EC Number: 235-985-8
• SMILES: CC(C)(C1=CC=C(C=C1)OC2=CC=C(C=C2)N)C3=CC=C(C=C3)OC4=CC=C(C=C4)N

Properties

• Density: 1.2$+/-$0.1 g/cm³ Calc.^*
• Melting point: 127 - 130 $degree$C (Expl.)
• Boiling point: 587.1$+/-$50.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 322.8$+/-$23.8 $degree$C (Calc.)^*
• Index of refraction: 1.641 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H317-H319-H335-H413
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410

Discovery and Applications

4,4'-(4,4'-Isopropylidenediphenyl-1,1'-diyldioxy)dianiline is an aromatic diamine compound in which two para-aminophenyl groups are connected through ether linkages to a central 4,4'-isopropylidenediphenyl unit. This compound is a multifunctional monomer widely used in the synthesis of high-performance polymers, particularly polyimides and epoxy resins. Its symmetrical structure, rigid aromatic core, and reactive amino groups make it a valuable building block for materials requiring thermal stability, mechanical strength, and chemical resistance.

The molecular structure features a central bisphenol-like moiety, where the two phenyl rings are connected via an isopropylidene bridge, forming a 4,4'-isopropylidenediphenyl unit. This core is linked to two para-aminophenoxy groups, providing a total of two primary amine functionalities. The combination of ether linkages and the bulky isopropylidene unit introduces flexibility in processing while maintaining rigidity in the polymer backbone. The amino groups are highly reactive toward electrophiles, enabling polymerization and crosslinking reactions.

Synthesis of this compound typically involves the nucleophilic substitution of bisphenol A derivatives with protected aminophenol units, followed by deprotection to yield the free amino groups. Such strategies ensure the proper placement of functional groups and preservation of the symmetrical structure, producing a high-purity monomer suitable for polymer applications.

In polymer chemistry, 4,4'-(4,4'-isopropylidenediphenyl-1,1'-diyldioxy)dianiline serves as a diamine monomer for polyimide production. Reaction with aromatic dianhydrides produces polyimides with excellent thermal stability, mechanical properties, and chemical resistance. The isopropylidene group contributes to reduced chain packing and increased free volume, improving solubility and processability compared to fully aromatic diamines. These characteristics are important in electronic, aerospace, and coating applications.

The compound’s amino groups also allow its use in epoxy resins, where they react with epoxide groups to form highly crosslinked thermosetting networks. The combination of rigid aromatic segments and reactive sites produces resins with high glass transition temperatures, low moisture absorption, and strong adhesion properties. Such materials are widely applied in adhesives, coatings, and advanced composites.

Beyond polymer synthesis, this diamine serves as an intermediate in organic synthesis for functional derivatives. Its reactive amino groups can undergo acylation, alkylation, or condensation reactions, enabling the preparation of specialized molecules and functional materials. The bulky isopropylidene core influences steric properties and reaction selectivity, which is advantageous in designing complex molecules.

Overall, 4,4'-(4,4'-isopropylidenediphenyl-1,1'-diyldioxy)dianiline is a multifunctional aromatic diamine that combines reactive amino groups, a rigid central core, and ether linkages. These features make it an essential monomer for high-performance polymers and functional materials requiring thermal stability, mechanical strength, and controlled physical properties.

References

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DOI: 10.1007/s11998-024-01072-6

2025. Exploring the applicative potential of polyimides containing DOPO-functionalized triazine through straightforward blending technique. Journal of Materials Science.
DOI: 10.1007/s10853-025-10751-7

2024. Preparation of Super Slippery Surface of Polyimide Composite Microspheres. Polymer Science, Series B.
DOI: 10.1134/s1560090424601146