1,4-Bis(4-aminophenoxy)butane
[CAS# 6245-50-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Alkane
• Name: 1,4-Bis(4-aminophenoxy)butane
• Synonyms: 4-[4-(4-Aminophenoxy)butoxy]aniline; beta,beta'-Bi-p-phenetidine
• Molecular Formula: C₁₆H₂₀N₂O₂
• Molecular Weight: 272.34
• CAS Registry Number: 6245-50-7
• EC Number: 667-211-3
• SMILES: C1=CC(=CC=C1N)OCCCCOC2=CC=C(C=C2)N

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 502.0±35.0 ºC 760 mmHg (Calc.)^*
• Flash point: 284.4±19.6 ºC (Calc.)^*
• Index of refraction: 1.608 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS09 Warning
• Hazard Statements: H400
• Precautionary Statements: P273-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400

Discovory and Applicatios

1,4-Bis(4-aminophenoxy)butane is an aromatic diamine with the molecular formula C₁₆H₂₀N₂O₂. Structurally, it consists of a butane backbone substituted at the 1 and 4 positions with 4-aminophenoxy groups, where each phenyl ring bears an amino group at the para position and is connected to the aliphatic spacer via an ether linkage. This combination of nucleophilic amino groups, aromatic rings, and a flexible butyl linker provides both reactivity and solubility characteristics suitable for polymer synthesis. The compound typically appears as a pale yellow to off-white solid, soluble in polar organic solvents such as dimethylformamide, acetone, and ethanol, but sparingly soluble in water.

1,4-Bis(4-aminophenoxy)butane is primarily used as a monomer in the synthesis of high-performance polymers. Its amino groups react readily with dianhydrides, diacid chlorides, or epoxides to form polyimides, polyamides, or epoxy-based networks. The aromatic rings provide rigidity and thermal stability, while the butyl ether spacer imparts flexibility, enhancing processability and mechanical properties. This combination makes it suitable for applications in coatings, adhesives, electronic materials, and other high-performance polymer systems.

The amino groups also allow further functionalization through acylation, sulfonation, or Schiff base formation, enabling the preparation of advanced materials with tailored chemical, mechanical, and surface properties. Its structural features facilitate the design of polymers with a controlled balance between rigidity, flexibility, and thermal resistance.

Synthetically, 1,4-bis(4-aminophenoxy)butane is typically prepared by nucleophilic aromatic substitution of 4-nitrophenol with 1,4-dihalobutane, followed by reduction of the nitro groups to amino groups. Purification is generally achieved through recrystallization or chromatographic techniques to obtain material suitable for polymerization or further chemical modifications.

Overall, 1,4-bis(4-aminophenoxy)butane is a versatile aromatic diamine monomer that combines reactive amino groups, a rigid aromatic core, and a flexible ether-linked butyl spacer. Its properties make it a valuable intermediate for high-performance polymers, functionalized materials, and applications requiring a balance of thermal stability, chemical reactivity, and mechanical flexibility.

References

2024. Flame Retardation of Polyamide 6 by Electro-Sprayed Phosphorus�Copper Complex Supported by Layered Silicate. Journal of Materials Engineering and Performance.
DOI: 10.1007/s11665-024-10344-6

2010. Novel poly(ether-amide)s derived from 1,4-(4-carboxy phenoxy)butane and ethereal diamines: Synthesis and properties. Macromolecular Research, 18(12).
DOI: 10.1007/s13233-010-1213-6