Cas no 59939-72-9 (1-(4-bromobenzoyl)piperazine)

1-(4-Bromobenzoyl)piperazine is a brominated aromatic compound featuring a piperazine moiety, commonly utilized as an intermediate in pharmaceutical and organic synthesis. Its key advantages include high purity and stability, making it suitable for precise chemical reactions. The presence of the 4-bromobenzoyl group enhances its reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, facilitating the synthesis of complex molecules. The piperazine ring contributes to its versatility in medicinal chemistry, particularly in the development of bioactive compounds. This compound is typically handled under controlled conditions to ensure optimal performance in research and industrial applications.
1-(4-bromobenzoyl)piperazine structure
1-(4-bromobenzoyl)piperazine structure
Product Name:1-(4-bromobenzoyl)piperazine
CAS No:59939-72-9
MF:C11H13BrN2O
MW:269.137721776962
MDL:MFCD09037861
CID:950942
PubChem ID:11277209
Update Time:2025-06-10

1-(4-bromobenzoyl)piperazine Chemical and Physical Properties

Names and Identifiers

    • (4-bromophenyl)(piperazin-1-yl) methanone
    • (4-bromophenyl)-piperazin-1-ylmethanone
    • 1-p-Brombenzoyl-piperazin
    • 1-(4-bromobenzoyl)piperazine
    • A832545
    • A1-04196
    • DTXSID20460985
    • EN300-64096
    • 59939-72-9
    • GS3267
    • Z228586806
    • (4-Bromophenyl)(piperazin-1-yl)methanone
    • CHEMBL4557051
    • (4-bromophenyl)-piperazin-1-yl-methanone
    • SCHEMBL13600346
    • AKOS000132952
    • MFCD09037861
    • (4-Bromo-phenyl)-piperazin-1-yl-methanone
    • (4-bromophenyl)-(1-piperazinyl)methanone
    • MDL: MFCD09037861
    • Inchi: 1S/C11H13BrN2O/c12-10-3-1-9(2-4-10)11(15)14-7-5-13-6-8-14/h1-4,13H,5-8H2
    • InChI Key: WLJZWLGUPJDGIL-UHFFFAOYSA-N
    • SMILES: BrC1C=CC(=CC=1)C(N1CCNCC1)=O

Computed Properties

  • Exact Mass: 268.02100
  • Monoisotopic Mass: 268.02113g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 221
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.4
  • Topological Polar Surface Area: 32.3?2

Experimental Properties

  • PSA: 32.34000
  • LogP: 1.76120

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Additional information on 1-(4-bromobenzoyl)piperazine

Professional Introduction to 1-(4-bromobenzoyl)piperazine (CAS No. 59939-72-9)

1-(4-bromobenzoyl)piperazine, chemically designated as 1-(4-bromobenzoyl)piperazine, is a significant compound in the realm of pharmaceutical chemistry and medicinal research. With a CAS number of 59939-72-9, this molecule has garnered attention due to its versatile applications in the synthesis of bioactive molecules and potential therapeutic agents. The presence of a bromobenzoyl group and a piperazine ring endows it with unique chemical properties that make it a valuable intermediate in the development of novel drugs.

The structure of 1-(4-bromobenzoyl)piperazine consists of a piperazine core substituted with a 4-bromobenzoyl moiety. This arrangement contributes to its reactivity and makes it a useful building block for further chemical modifications. The bromine atom in the benzoyl group enhances its electrophilicity, facilitating various coupling reactions that are pivotal in drug synthesis. Consequently, this compound has been widely employed in the preparation of more complex molecules, including those targeting neurological and inflammatory disorders.

In recent years, there has been growing interest in exploring the pharmacological potential of piperazine derivatives. The piperazine scaffold is known for its ability to interact with biological targets such as G-protein coupled receptors (GPCRs) and enzymes, making it a cornerstone in the design of drugs for conditions like depression, schizophrenia, and epilepsy. The introduction of a bromobenzoyl group into this framework expands its utility by providing additional sites for functionalization, enabling the creation of highly specific ligands.

One of the most compelling applications of 1-(4-bromobenzoyl)piperazine lies in its role as a precursor in the synthesis of kinase inhibitors. Kinases are enzymes that play a crucial role in cell signaling pathways, and their dysregulation is often associated with cancer and inflammatory diseases. By modifying the piperazine core with various substituents, researchers have been able to develop potent inhibitors that selectively target specific kinases. For instance, studies have shown that derivatives of 1-(4-bromobenzoyl)piperazine can serve as lead compounds for developing small-molecule inhibitors with significant therapeutic potential.

Moreover, the compound has found utility in the development of novel antimicrobial agents. The bromobenzoyl group enhances the compound's ability to interact with bacterial enzymes and cell membranes, leading to mechanisms that disrupt bacterial growth. This has opened up new avenues for combating drug-resistant bacteria, which pose a significant threat to global health. Researchers are currently investigating how modifications to the piperazine ring can improve antimicrobial efficacy while minimizing toxicity.

The synthetic methodologies for preparing 1-(4-bromobenzoyl)piperazine have also seen considerable advancements. Traditional approaches often involve multi-step reactions that can be time-consuming and require harsh conditions. However, recent innovations have led to more efficient synthetic routes that are both cost-effective and environmentally friendly. For example, catalytic methods using transition metals have been employed to facilitate key transformations, reducing the need for excessive reagents and solvents.

The role of computational chemistry in optimizing the synthesis and application of 1-(4-bromobenzoyl)piperazine cannot be overstated. Advanced computational techniques allow researchers to predict the behavior of molecules before they are synthesized, saving valuable time and resources. Molecular modeling studies have helped identify optimal reaction conditions and predict the biological activity of derivatives, accelerating the drug discovery process.

In conclusion, 1-(4-bromobenzoyl)piperazine (CAS No. 59939-72-9) is a multifaceted compound with broad applications in pharmaceutical research and drug development. Its unique structural features make it an invaluable intermediate for synthesizing bioactive molecules targeting various diseases. As research continues to uncover new therapeutic possibilities, this compound is poised to play an even greater role in shaping the future of medicine.

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