N-(2-Hydroxyethyl)piperazine
[CAS# 103-76-4]

Identification

• Classification: API >> Antiparasitic drug >> Anthelmintic
• Name: N-(2-Hydroxyethyl)piperazine
• Synonyms: 1-Piperazineethanol
• Molecular Formula: C₆H₁₄N₂O
• Molecular Weight: 130.19
• CAS Registry Number: 103-76-4
• EC Number: 203-142-3
• SMILES: C1CN(CCN1)CCO

Properties

• Density: 1.061 g/mL (Expl.)
• Melting point: -38.5 °C (Expl.)
• Boiling point: 246 °C (Expl.)
• Refractive index: 1.506 (Expl.)
• Flash point: 135 °C (Expl.)
• Water solubility: MISCIBLE

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H315-H318-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	1	H310
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	1	H300
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

N-(2-Hydroxyethyl)piperazine, also known as HEPP, is an organic compound widely used in various applications due to its versatile properties. It belongs to the class of piperazine derivatives, which are characterized by a six-membered heterocyclic structure containing two nitrogen atoms. The addition of a hydroxyethyl group to the piperazine ring imparts both hydrophilic and lipophilic characteristics to the molecule, making it useful in a broad range of chemical and industrial processes.

The discovery of N-(2-Hydroxyethyl)piperazine dates back to the early 20th century, as researchers began to explore the chemical properties and potential applications of piperazine derivatives. Piperazine itself had already found applications in medicinal chemistry, and the introduction of functional groups like the hydroxyethyl group enhanced its properties, leading to further investigation into its utility in various fields.

In terms of its applications, N-(2-Hydroxyethyl)piperazine is primarily used as a building block in the synthesis of other chemicals. It serves as an intermediate in the preparation of surfactants, chelating agents, and corrosion inhibitors. Its ability to form stable complexes with metal ions makes it particularly useful in the formulation of agents for water treatment and industrial cleaning. These complexes can effectively prevent the deposition of minerals and help control scale formation in water systems, making HEPP valuable in the maintenance of industrial equipment, such as boilers and cooling systems.

Additionally, N-(2-Hydroxyethyl)piperazine has found significant use in the pharmaceutical and biotechnology industries. It can be used to prepare derivatives with enhanced biological activity. The compound's amine functionality allows it to participate in reactions that yield biologically active molecules, such as antimicrobial agents and anticancer compounds. By modifying the hydroxyethyl group or introducing other substituents onto the piperazine ring, researchers can tailor the compound's properties to suit specific therapeutic needs.

Another notable application of N-(2-Hydroxyethyl)piperazine is in the synthesis of polymeric materials. It can be used to prepare polyamine-based polymers that have desirable properties such as flexibility, adhesion, and resistance to various environmental factors. These polymers are utilized in coatings, adhesives, and sealants, where chemical resistance and durability are critical.

N-(2-Hydroxyethyl)piperazine also plays a role in the development of ion exchange resins. Its ability to interact with various ions makes it useful in creating resins for water purification, which are widely applied in both domestic and industrial water treatment systems.

In summary, N-(2-Hydroxyethyl)piperazine is a valuable chemical with diverse applications across industries such as pharmaceuticals, water treatment, polymer production, and more. Its unique combination of functional groups enhances its chemical reactivity, making it a versatile component in the synthesis of a variety of useful compounds and materials.

References

2023. Novel aloe emodin-hydroxyethyl piperazine hybrid dihydrochloride induces oral cancer CAL-27 cells apoptosis through ROS production, DNA damage and mitochondrial pathways. Medicinal Chemistry Research, 32(12).
DOI: 10.1007/s00044-023-03157-0

2024. Piperazine-derived ionizable lipids for enhanced mRNA delivery and cancer immunotherapy. Nano Research, 17(11).
DOI: 10.1007/s12274-024-6575-8