Cas no 226068-82-2 (Ethyl 2-(piperazin-2-yl)acetate)

Ethyl 2-(piperazin-2-yl)acetate is a versatile intermediate in organic synthesis, particularly valued for its piperazine backbone, which is integral to many pharmacologically active compounds. Its ester functionality enhances reactivity, facilitating further derivatization, while the piperazine moiety offers a rigid, nitrogen-rich scaffold for constructing heterocyclic systems. This compound is commonly employed in medicinal chemistry for the development of CNS-targeting agents, antimicrobials, and other bioactive molecules. Its balanced solubility in both polar and nonpolar solvents makes it suitable for diverse reaction conditions. High purity grades are available to ensure reproducibility in research and industrial applications.
Ethyl 2-(piperazin-2-yl)acetate structure
226068-82-2 structure
Product Name:Ethyl 2-(piperazin-2-yl)acetate
CAS No:226068-82-2
MF:C8H16N2O2
MW:172.224842071533
CID:244787
PubChem ID:10749720
Update Time:2025-05-20

Ethyl 2-(piperazin-2-yl)acetate Chemical and Physical Properties

Names and Identifiers

    • Ethyl 2-(piperazin-2-yl)acetate
    • 2-Piperazineaceticacid, ethyl ester
    • ethyl 2-piperazin-2-ylacetate
    • AG-E-64686
    • AK-68660
    • CTK4E9811
    • MolPort-000-006-192
    • SureCN123309
    • Ethyl2-(piperazin-2-yl)acetate
    • DTXSID30444291
    • 2-Piperazineacetic acid, ethyl ester
    • SCHEMBL123309
    • 2-piperazineacetic acid ethyl ester
    • 226068-82-2
    • DB-114393
    • Inchi: 1S/C8H16N2O2/c1-2-12-8(11)5-7-6-9-3-4-10-7/h7,9-10H,2-6H2,1H3
    • InChI Key: LPCVZQJECZADQY-UHFFFAOYSA-N
    • SMILES: O(CC)C(CC1CNCCN1)=O

Computed Properties

  • Exact Mass: 172.12128
  • Monoisotopic Mass: 172.121177757g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 4
  • Complexity: 150
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.6
  • Topological Polar Surface Area: 50.4?2

Experimental Properties

  • Density: 0.997
  • Boiling Point: 257.9°Cat760mmHg
  • Flash Point: 109.8°C
  • Refractive Index: 1.44
  • PSA: 50.36

Ethyl 2-(piperazin-2-yl)acetate Pricemore >>

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Additional information on Ethyl 2-(piperazin-2-yl)acetate

Research Brief on Ethyl 2-(piperazin-2-yl)acetate (CAS: 226068-82-2) in Chemical Biology and Pharmaceutical Applications

Ethyl 2-(piperazin-2-yl)acetate (CAS: 226068-82-2) has emerged as a compound of significant interest in chemical biology and pharmaceutical research due to its unique structural features and potential therapeutic applications. Recent studies have focused on its role as a versatile building block in medicinal chemistry, particularly in the synthesis of novel bioactive molecules targeting neurological disorders and infectious diseases.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's utility as a key intermediate in the development of selective serotonin reuptake inhibitors (SSRIs) with improved blood-brain barrier penetration. The research team utilized Ethyl 2-(piperazin-2-yl)acetate as a core scaffold to develop a series of derivatives showing enhanced binding affinity to serotonin transporters while minimizing off-target effects.

In antimicrobial research, a recent Nature Communications article (2024) reported the compound's incorporation into novel quinolone-azetidine hybrids exhibiting potent activity against multidrug-resistant Gram-positive pathogens. The piperazine moiety in Ethyl 2-(piperazin-2-yl)acetate was found to be crucial for maintaining antibacterial activity while reducing cytotoxicity in mammalian cells.

Structural optimization studies have revealed that the ethyl ester group in 226068-82-2 provides an excellent balance between lipophilicity and metabolic stability, making it particularly valuable in CNS drug discovery. Recent molecular modeling analyses suggest the compound's potential for developing allosteric modulators of G-protein coupled receptors (GPCRs), with several patent applications filed in early 2024.

Ongoing clinical trials (Phase I/II) are investigating derivatives of Ethyl 2-(piperazin-2-yl)acetate as potential treatments for neurodegenerative diseases, with preliminary results showing promising neuroprotective effects in cellular and animal models of Parkinson's disease. The compound's ability to chelate metal ions may contribute to its observed antioxidant properties in these studies.

From a synthetic chemistry perspective, recent advances in catalytic asymmetric synthesis have enabled more efficient production of enantiomerically pure Ethyl 2-(piperazin-2-yl)acetate, addressing previous challenges in stereochemical control. This development has significant implications for the compound's use in chiral drug synthesis.

Future research directions include exploring the compound's potential in targeted drug delivery systems and as a component of PROTACs (proteolysis targeting chimeras) for protein degradation therapies. The unique structural features of 226068-82-2 continue to make it a valuable tool in modern drug discovery and chemical biology research.

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