2252-63-3 | 1-(4-Fluorophenyl)piperazine

CAS:2252-63-3 | 1-(4-Fluorophenyl)piperazine,Description

1-(4-Fluorophenyl)piperazine is a chemical compound that has been the subject of various research studies due to its potential applications in medicinal chemistry and imaging. It is a structural motif present in several compounds with diverse biological activities, including antimicrobial properties and the ability to act as ligands for receptor studies in positron emission tomography (PET) imaging.

Synthesis Analysis

The synthesis of 1-(4-Fluorophenyl)piperazine derivatives involves various chemical reactions, often aiming to introduce functional groups that may enhance the biological activity of the compound. For instance, N-alkyl and N-sulfonyl derivatives of 1-[bis(4-fluorophenyl)-methyl]piperazine have been synthesized and characterized by IR and 1H NMR, showing potent antimicrobial activities against a range of bacteria. Another study describes the synthesis of a related compound intended for imaging dopamine D4 receptors, which was achieved through electrophilic fluorination of a trimethylstannyl precursor. Additionally, rapid synthesis methods have been developed for the preparation of 1-(4-[18F]fluorophenyl)piperazine, demonstrating its utility in the synthesis of selective ligands for PET studies.

Molecular Structure Analysis

The molecular structure of 1-(4-Fluorophenyl)piperazine derivatives has been extensively studied using techniques such as X-ray crystallography. These studies have revealed details about the crystal and molecular structure, including the conformation of the piperazine ring and the orientation of the fluorophenyl group. For example, the crystal structure of a related compound showed that the piperazine ring adopts a chair conformation and the benzimidazole ring is nearly planar. In another study, the crystal structure of a tert-butyl piperazine-1-carboxylate derivative was determined, highlighting weak intermolecular interactions that contribute to the three-dimensional architecture of the compound.

Chemical Reactions Analysis

1-(4-Fluorophenyl)piperazine and its derivatives undergo various chemical reactions that are crucial for their synthesis and functionalization. These reactions include condensation, displacement, and electrophilic fluorination, among others. The reactivity of these compounds allows for the introduction of diverse substituents, which can significantly alter their biological activity and physical properties.

Physical and Chemical Properties Analysis

The physical and chemical properties of 1-(4-Fluorophenyl)piperazine derivatives are influenced by their molecular structure and the substituents present. These properties include solubility, melting point, and stability, which are important for their potential applications. For instance, thermal and crystallographic studies have been conducted to determine the stability and lattice interactions of these compounds, providing insights into their behavior under various conditions. The presence of fluorine atoms often affects the electronic properties of the molecule, which can be crucial for their activity as ligands or therapeutic agents.

Scientific Research Applications

Synthesis and Chemical Applications

• Synthesis of Flunarizine and its Isomers : Research by Shakhmaev et al. (2016) highlights the industrial synthesis of Flunarizine, a drug used for treating migraines and epilepsy. It involves the condensation of N-cynnamylpiperazine with bis(4-fluorophenyl)chloromethane, where 1-(4-Fluorophenyl)piperazine is a key intermediate.
• Development of Antagonist for 5-HT1A Receptors : Plenevaux et al. (2000) discuss research on [18F]4-(2′-methoxyphenyl)-1-[2′-[N-(2′′-pyridinyl)-p-fluorobenzamido]ethyl]-piperazine, an antagonist for studying serotonergic neurotransmission with PET. This compound incorporates 1-(4-Fluorophenyl)piperazine in its structure.
• Synthesis of Novel Piperazine Derivatives : The work of Balaraju et al. (2019) focuses on the synthesis of novel 1-(2-fluorophenyl)-3-(4-((pyridine-2-yl) methyl) piperazin-1-yl)-1H-indazole, significant in medicinal chemistry. It demonstrates the versatility of 1-(4-Fluorophenyl)piperazine in creating new medicinal compounds.

Medicinal Applications

• Antitumor Activity : Ding et al. (2016) describe the synthesis of 1,2,4-triazole Schiff bases containing 1-[bi-(4-fluorophenyl)methyl]piperazine, showing significant antitumor activity, particularly against CDC25B.
• Antimicrobial Studies : Chandra et al. (2006) synthesized novel 1-[bis(4-fluorophenyl)-methyl]piperazine derivatives, which demonstrated potent antimicrobial activities against a variety of bacterial strains.

Computational and Analytical Studies

• Conformational Analysis and Alzheimer’s Disease Treatment : Celik (2022) conducted a comprehensive study on 1-(4-Fluorophenyl)Piperazine, including molecular docking studies to predict its potential as a drug for improving Alzheimer's disease treatment.
• Crystal Structure Analysis : Sanjeevarayappa et al. (2015) focused on the crystal structure and X-ray diffraction studies of tert-butyl 4-(5-(3-fluorophenyl)-1,2,4-oxadiazol-3-yl) piperazine-1-carboxylate, illustrating the structural applications of 1-(4-Fluorophenyl)piperazine derivatives.

Environmental and Green Chemistry

• Green Synthesis and Evaluation of Schiff Bases : The research by Ding et al. (2016) also highlights the green synthesis of 1,2,4-triazole Schiff bases, showcasing environmentally friendly approaches in the chemical synthesis involving 1-(4-Fluorophenyl)piperazine.

Safety And Hazards

This chemical is considered hazardous by the 2012 OSHA Hazard Communication Standard (29 CFR 1910.1200). It has been classified for acute oral toxicity, acute dermal toxicity, skin corrosion/irritation, serious eye damage/eye irritation, and specific target organ toxicity (single exposure) with the target organ being the respiratory system.

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