1,3-Bis(4-aminophenoxy)propane
[CAS# 52980-20-8]

Identification

• Name: 1,3-Bis(4-aminophenoxy)propane
• Synonyms: 4,4'-[1,3-Propanediylbis(oxy)]bis[benzenamine]; 1,3-Bis(4-aminophenoxy)propane; 4-[3-(4-Aminophenoxy)propoxy]aniline
• Molecular Formula: C₁₅H₁₈N₂O₂
• Molecular Weight: 258.32
• CAS Registry Number: 52980-20-8
• EC Number: 622-193-6
• SMILES: C1=CC(=CC=C1N)OCCCOC2=CC=C(C=C2)N

Properties

• Solubility: Very slightly soluble (0.16 g/L) (25 °C), Calc.^*
• Density: 1.177±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 109-112 °C^**

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

^** Faghihi, Khalil

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H319
• Safety Statements: P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

1,3-Bis(4-aminophenoxy)propane is an aromatic diamine with the molecular formula C₁₅H₁₈N₂O₂. Structurally, it consists of a propane backbone substituted at the 1 and 3 positions with 4-aminophenoxy groups, in which a phenyl ring bearing an amino group at the para position is linked via an ether bond to the central propyl chain. This combination of aromatic amino groups and a flexible aliphatic linker provides both reactivity and solubility characteristics that are valuable in 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.

1,3-Bis(4-aminophenoxy)propane is primarily used as a monomer in polymer chemistry. Its amino groups readily react with dianhydrides, diacid chlorides, or epoxides to form polyimides, polyamides, or epoxy-based networks. The aromatic diamine structure contributes rigidity and thermal stability to the resulting polymers, while the propyl ether linkage imparts flexibility and processability. This balance of rigidity and flexibility makes the compound especially valuable for high-performance materials in coatings, adhesives, and electronic applications.

In addition to polymerization, the amino groups allow the compound to act as a precursor for functionalized derivatives through reactions such as acylation, sulfonation, or Schiff base formation. Such modifications expand its utility in materials science and chemical synthesis.

Synthetically, 1,3-Bis(4-aminophenoxy)propane can be prepared by nucleophilic aromatic substitution of 4-nitrophenol with 1,3-dihalopropane, followed by reduction of the nitro groups to amines. Purification typically involves recrystallization or column chromatography to achieve the desired purity for polymerization or functionalization reactions.

Overall, 1,3-Bis(4-aminophenoxy)propane is a versatile aromatic diamine monomer that combines reactive amino groups, an ether-linked propyl spacer, and aromatic rigidity. Its structural features make it a valuable building block for high-performance polymers, functionalized materials, and other applications requiring a combination of thermal stability, chemical reactivity, and mechanical flexibility.

References

2019. Synthesis and optical properties of semi-fluorinated poly(ether imide)s derived from non-fluorinated 1,4-bis(3,4-dicarboxyphenoxy)benzene dianhydride (HQDPA) and trifluoromethyl-substituted diamines. Journal of Materials Research, 34(3).
DOI: 10.1557/jmr.2018.440

2014. New poly(ether-imide)/MWCNT nanocomposite. Journal of Thermal Analysis and Calorimetry, 116(3).
DOI: 10.1007/s10973-014-3682-x