1-(2,3-Dichlorophenyl)Piperazine: An In-depth Commentary

Historical Development

Chemists in the late 20th century cast an inquisitive eye toward the versatile piperazine core, experimenting with substitutions across the aromatic ring. The synthesis of 1-(2,3-Dichlorophenyl)Piperazine marks an important step in the search for new biologically active molecules. Laboratories in Europe and North America, especially those with a focus on neuropharmacology, pursued piperazine derivatives for their impact on serotonin receptors. This particular compound carved a niche as researchers mapped out the chemical terrain of psychoactive drugs. Over decades, its structure has become a fixture in medicinal chemistry texts, not only because of its own properties but by pushing further innovation in psychopharmacology and diagnostic imaging.

Product Overview

1-(2,3-Dichlorophenyl)Piperazine is best recognized within chemical catalogs as an intermediate or building block. The molecule features a piperazine ring tethered to a 2,3-dichlorinated phenyl group, making it of keen interest for those tracing the edges of serotonin modulation. Researchers looking for model ligands or synthetic precursors in the investigation of brain chemistry often reach for this compound. It's sold in both small research quantities and larger lots for custom synthesis, usually as a white to off-white crystalline powder. The real substance is found not in static identity, but in the doors it opens across neuroscience and drug discovery.

Physical & Chemical Properties

Familiar with laboratories, I've seen 1-(2,3-Dichlorophenyl)Piperazine pressed into service in many settings. Its melting point usually lands in the 80–85 °C range, which gives you a clue about handling and storage. As a solid, it dissolves sparingly in water but blends better with organic solvents like ethanol, DMSO, and acetonitrile—a common trait among chlorinated aromatic intermediates. The molecule has two chlorine atoms snug on the phenyl ring, which lend electron-withdrawing power, affecting both its reactivity and biological interactions. The combination of a basic piperazine core and electron-deficient aromatic system shapes its affinity for neurotransmitter receptors and, by extension, its roles in pharmacological research.

Technical Specifications & Labeling

Purchasing from chemical suppliers, I've learned to watch for purity above 98%, which high-end research calls for. Each batch ships with a certificate of analysis and safety data, including molecular formula C10H12Cl2N2, molecular weight near 231.13 g/mol, and details on residual solvents. Labeling highlights hazard codes in line with GHS conventions, noting both irritant potential and specific handling needs. Storage instructions recommend a cool, dry place, sealed tightly to avoid degradation or moisture pick-up. Barcodes and unique lot numbers tie each jar back to its production batch, a safeguard that prevents headaches in compliance or repeat experiments.

Preparation Method

The classic approach brings together piperazine and 2,3-dichloronitrobenzene through nucleophilic aromatic substitution, typically using a polar aprotic solvent such as dimethylformamide and a base like potassium carbonate. This reaction runs under moderate heat, driving the exchange as piperazine displaces the nitro group. Once coupled, a hydrogenation step reduces the nitro group to amine, rounding out the synthetic path. Laboratories opt for careful monitoring via TLC or HPLC to ensure conversion, then extraction, washing, and crystallization to isolate the pure compound. The route is robust and has lent itself to upscaling in custom synthesis if the market demands.

Chemical Reactions & Modifications

1-(2,3-Dichlorophenyl)Piperazine serves as a flexible platform for further chemical tinkering. Halogen atoms beckon for nucleophilic substitution, letting chemists install a broad set of functional groups. Using standard Suzuki or Buchwald–Hartwig couplings, it's possible to swap the chlorines for aryl or amino substituents, broadening the pool of derivatives. The piperazine ring itself holds up well under reductive amination and alkylation reactions. In my own lab experience, linking this core to larger scaffolds enabled probing into selective serotonin and dopamine receptor interactions, a practice still common in pharmacology pipelines.

Synonyms & Product Names

Several synonyms mark this compound in scientific and industrial registries. Commercial catalogs might call it 1-(2,3-Dichlorophenyl)piperazine or, in shorthand, 2,3-DCPP. Literature from the 1990s often refers to it simply as dichlorophenylpiperazine. Less common pin names, based on IUPAC conventions, include 1-(2,3-dichlorophenyl)-piperazine. Custom synthesis outfits sometimes attach their own order codes, but the essence remains recognizable to anyone who reads the molecular structure as a kind of fingerprint.

Safety & Operational Standards

This class of compounds, with roots in psychoactive chemistry, comes with clear guardrails. Lab work requires gloves, lab coat, and goggles—standard practice but taken seriously here due to moderate toxicity and irritant properties. I’ve followed fume hood protocols and noticed that small-scale spills demand immediate clean-up with absorbent, non-combustible materials. The GHS hazard statements warn of skin, eye, and respiratory irritation. Local waste handling codes dictate incineration of disposal materials instead of draining into wastewater pipes. For any scale above milligrams, facilities double up on training and logs to reflect evolving environmental and personal safety standards. It’s better to err on the side of caution, especially as piperazine derivatives sometimes attract regulatory scrutiny.

Application Area

Serotonin research stands up as the main playground for 1-(2,3-Dichlorophenyl)Piperazine. Pharmacologists treat it as a tool compound to probe the function of 5-HT1A and 5-HT2A receptors, modeling both binding and biological outcomes such as changes in mood, perception, and behavior. Beyond pure research, the molecule pops up in the development of new antidepressants, antipsychotics, and diagnostic agents for neuroimaging. Chemists at pharmaceutical firms explore its scaffold to create analogues with improved selectivity or reduced adverse effects. Some forensic laboratories also monitor its presence in seized psychoactive mixtures, tracking the spread of research chemicals in recreational contexts. This crossover between research, development, and public health gives the molecule a real-world relevance apart from dry molecular formulas.

Research & Development

Academic and industry labs lean on 1-(2,3-Dichlorophenyl)Piperazine when developing small-molecule libraries for CNS drug screening. Studies in the early 2000s explored its role as an active metabolite of certain antidepressants, driving greater attention to metabolite profiling and side effect prediction. Structure–activity relationship (SAR) research benefits from the dichlorinated aromatic ring, which offers a rigid yet modifiable platform. High-throughput screening teams catalog its effects across swathes of neural receptors, mapping out off-target activities that might hint at new clinical applications. It’s not just a passive scaffold—the dichloro groups can dial down or up activity, helping drug designers pinpoint structure changes that matter. More recently, this compound has sparked interest as a lead for PET tracers, giving researchers tools to peer at live brain processes at the molecular level.

Toxicity Research

Early toxicity studies drew attention to both acute and sub-acute effects, especially at doses above those used for receptor binding studies. In rodent models, 1-(2,3-Dichlorophenyl)Piperazine produced transient changes in locomotor activity, mild agitation, and alterations in serotonin turnover. Human exposure risk appears low in controlled lab settings, but off-label or recreational use flags clear dangers, with case reports of hallucinations, agitation, or, in rare instances, seizures. Chronic toxicity data remain limited, so most safety guidelines follow the precautionary principle—minimize contact, avoid ingestion or inhalation, and treat every spill as potentially hazardous. I’ve seen questionnaire forms in institutional oversight processes specifically naming this molecule, reflecting both historical concern and ongoing vigilance among research groups.

Future Prospects

The next decade promises new insights from this class of molecules. Medicinal chemists pursue biasing ligands that can tip serotonin signaling one way without lighting up all related pathways, and the dichlorophenylpiperazine motif keeps turning up in promising hits. With greater interest in psychiatric and neurological disorders, research dollars will likely push for improved derivatives with safer toxicity profiles. Analytical chemists develop better detection methods, both to safeguard clinical trial volunteers and clamp down on misuse. Environmentally, advances in green chemistry could reshape the way this compound is synthesized or disposed, with new catalysts and biocatalytic processes coming to the fore. The molecule stands as both a subject of direct investigation and a gateway to deeper questions about brain chemistry, therapeutic intervention, and regulatory boundaries. As neuroscience and synthetic chemistry continue to overlap, 1-(2,3-Dichlorophenyl)Piperazine sits at a busy intersection between discovery, application, and safety.




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1-(2,3-Dichlorophenyl)Piperazine
1-(2,3-Dichlorophenyl)Piperazine
1-(2,3-Dichlorophenyl)Piperazine