1,4-Bis(3-aminopropyl)piperazine
[CAS# 7209-38-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Piperazine
• Name: 1,4-Bis(3-aminopropyl)piperazine
• Synonyms: N,N'-Bis(3-aminopropyl)piperazine
• Molecular Formula: C₁₀H₂₄N₄
• Molecular Weight: 200.32
• CAS Registry Number: 7209-38-3
• EC Number: 230-589-1
• SMILES: C1CN(CCN1CCCN)CCCN

Properties

• Density: 0.973 g/mL (Expl.)
• Melting point: 15 ºC (Expl.)
• Boiling point: 150-152 ºC (2 mmHg) (Expl.)
• Refractive index: 1.502 (Expl.)
• Flash point: 163 ºC (Expl.)

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H312-H314-H318-H412
• Precautionary Statements: P260-P264-P264+P265-P270-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Skin sensitization	Skin Sens.	1	H317

• Transport Information: UN 2735

Discovory and Applicatios

1,4-Bis(3-aminopropyl)piperazine is a chemical compound that belongs to the family of piperazine derivatives. This compound consists of a piperazine ring with two 3-aminopropyl groups attached to the nitrogen atoms at positions 1 and 4. It has gained attention due to its versatile chemical structure and its applications in various fields, including pharmaceuticals, polymer chemistry, and industrial processes.

The discovery of 1,4-Bis(3-aminopropyl)piperazine can be traced back to the broader research on piperazine derivatives, which have been extensively studied for their biological and chemical properties. Piperazine itself is a six-membered ring compound containing two nitrogen atoms, and it has been known for its biological activity and industrial uses. The introduction of the 3-aminopropyl groups to the piperazine ring in 1,4-Bis(3-aminopropyl)piperazine enhances its chemical reactivity and allows it to interact with various molecules, making it a valuable building block for the synthesis of more complex compounds.

One of the primary applications of 1,4-Bis(3-aminopropyl)piperazine is in the pharmaceutical industry, where it serves as an intermediate in the synthesis of drugs. It is particularly useful in the preparation of certain anti-depressant and anti-anxiety medications, as the compound’s structure shares similarities with other bioactive molecules. The 3-aminopropyl groups provide sites for further chemical modification, which is crucial in the development of new drug candidates. By altering the structure of 1,4-Bis(3-aminopropyl)piperazine, chemists can create a wide range of pharmaceutical compounds with varying therapeutic properties.

In addition to its use in pharmaceuticals, 1,4-Bis(3-aminopropyl)piperazine is also employed in the field of polymer chemistry. It is used as a monomer in the synthesis of various polymers, particularly those with applications in adhesives, coatings, and sealants. The amino groups on the molecule can react with other monomers or functional groups, allowing for the formation of cross-linked polymer networks. These polymers are known for their enhanced mechanical properties, such as strength and flexibility, and are widely used in industries that require durable materials.

Furthermore, 1,4-Bis(3-aminopropyl)piperazine has applications in the field of ion exchange resins. It can be incorporated into the structure of resins used for water purification, as the amino groups allow the material to interact with and remove certain ions from water. This property makes 1,4-Bis(3-aminopropyl)piperazine a valuable component in environmental protection technologies, where the need for efficient and selective ion removal is critical.

Another notable application of 1,4-Bis(3-aminopropyl)piperazine is in the development of surfactants and emulsifiers. These compounds are crucial in a variety of industrial applications, such as cleaning products, cosmetics, and paints. The amphiphilic nature of 1,4-Bis(3-aminopropyl)piperazine, which allows it to interact with both hydrophilic and hydrophobic substances, makes it an effective ingredient in the formulation of these products.

In conclusion, 1,4-Bis(3-aminopropyl)piperazine is a versatile chemical compound with a broad range of applications in industries such as pharmaceuticals, polymer chemistry, water treatment, and manufacturing. Its unique structure, featuring two 3-aminopropyl groups attached to a piperazine ring, allows for a variety of chemical reactions and interactions, making it a valuable building block for the synthesis of diverse compounds. As research into its properties and potential applications continues, it is likely that 1,4-Bis(3-aminopropyl)piperazine will play an increasingly important role in the development of new materials and therapeutic agents.

References

2023. A 2D open-framework cadmium(II) complex templated by 1,4-bis(3-aminopropyl)piperazine: crystal structure, optical properties, theoretical and biological study. Journal of the Iranian Chemical Society, 20(9).
DOI: 10.1007/s13738-023-02798-7

2003. Synthesis and antimalarial evaluation of new 1,4-bis(3-aminopropyl)piperazine derivatives. Bioorganic & Medicinal Chemistry Letters, 13(22).
DOI: 10.1016/j.bmcl.2003.07.008