Chemists have spent decades searching for piperidine derivatives that open new doors in medicinal chemistry and chemical biology, and 4-(4-Iodo-1H-Pyrazol-1-Yl)Piperidine has become one of those key molecular tools. Research papers from the early 2000s show pyrazole rings making their way into drug scaffolds, often to increase binding potential or tune pharmacological properties. The addition of an iodine atom to the pyrazole ring – an approach that gained traction with advances in halogenation methods – lent this molecule a unique role in radiochemistry and diagnostics. Organic and medicinal chemistry circles took notice, particularly as targeted modification of heterocycles like this one became more mainstream.
4-(4-Iodo-1H-Pyrazol-1-Yl)Piperidine appears as a bench-stable solid, light to medium yellow in hue, but its most significant feature is the iodine moiety at the pyrazole position. This feature makes the compound valuable for further derivatization or radiolabeling. Research teams often look for molecules like this as intermediates, especially when planning synthetic schemes around kinase inhibitors, ion channel modulators, or molecular probes for imaging. The molecule stands out not just for its reactivity but also its compatibility with commonly used solvents and its integration into broader synthetic routes.
Examining the structure, we find a six-membered saturated piperidine ring linked through its 4-position to a 1H-pyrazole that holds iodine at the 4-position. Its molecular formula clocks in at C8H12IN3, and the compound’s mass, topped by the hefty iodine atom, places it at roughly 289 g/mol. Most suppliers indicate it has a melting point in the region of 112–116°C. The compound dissolves well in DMSO and DMF, less so in less polar solvents, and its logP value sits on the higher side for a heteroaromatic. Under standard lab conditions, the compound resists rapid degradation, but exposure to strong bases or oxidants can cause it to decompose or lose iodide.
Reputable sources provide 4-(4-Iodo-1H-Pyrazol-1-Yl)Piperidine as a highly pure solid, with HPLC yields above 98%. Standard labeling covers the batch number, CAS registry number, chemical structure, recommended storage conditions, and the date of synthesis or repackaging. Keeping the compound dry and protected from light at 2–8°C or ambient temperatures ensures extended shelf life. Many users appreciate clear labeling indicating potential hazard classes and GHS pictogram requirements, considering the presence of the iodine atom, which can present specific health and environmental risks.
Synthetic routes usually start from commercially available 4-iodopyrazole or a suitably protected variant. Researchers combine this building block with piperidine through N-arylation, capitalizing on palladium-catalyzed cross-coupling such as Buchwald-Hartwig amination, using a suitable base and ligand. To maximize yield, reaction conditions are tuned for temperature and solvent polarity, often favoring a mild base like potassium carbonate and a polar aprotic solvent such as DMF. Workups typically require aqueous quenching and extraction, with careful chromatographic purification to separate side products and unreacted material. Lab teams with access to automated flash systems can streamline this process.
This compound offers multiple paths forward for further chemistry. The reactive iodine atom opens the door to Suzuki-Miyaura couplings for the introduction of aryl groups, Sonogashira reactions to add alkynes, or simply radioiodination for tracer studies. The pyrazole ring can also participate in electrophilic aromatic substitution, though its activity is tempered by the electron-withdrawing iodine. On the piperidine side, the nitrogen can be alkylated or amidated, enabling the attachment of fluorescent tags, biotin, or other probes for target engagement studies. Modern labs with access to parallel synthesis platforms often use this molecule as a scaffold to build compound libraries for high-throughput screening.
Literature and suppliers might refer to this molecule as 4-(4-Iodo-1H-pyrazol-1-yl)piperidine, 1-(4-Piperidinyl)-4-iodopyrazole, or by catalog numbers from supply houses. Its systematic IUPAC name keeps popping up in journals, but for everyday lab work, chemists often shorthand it to “Iodo-pyrazole piperidine” or “I-PYP.” Regardless of the label, the structure speaks louder than the name, as any chemist familiar with these rings can spot the key reactive handles on sight.
4-(4-Iodo-1H-Pyrazol-1-Yl)Piperidine calls for careful handling, using fully enclosed personal protective equipment—lab coats, nitrile gloves, and safety goggles—thanks to its potential to cause skin and respiratory irritation. Accidental inhalation of dust, although unlikely due to its crystalline nature, should be avoided by using a fume hood. Cleaning up any spills quickly and thoroughly, using inert absorbent materials, helps keep workspaces safe. Disposal requires precise tracking, especially with iodinated waste materials, to comply with institutional protocols and local environmental rules. Researchers working with radioiodinated analogs need to follow additional isolation and monitoring measures, and emergency eye-wash stations and safety showers help address exposure.
Medicinal chemistry regularly taps into the reactivity of this molecule to build kinase inhibitors, particularly those targeting signaling proteins implicated in cancer and autoimmune disorders. Imaging applications benefit from iodine-125 or iodine-131 radiolabeling, allowing precise mapping of molecular targets in living systems, a critical piece for the diagnosis and staging of certain tumors. Chemical biologists use it as a probe handle to pull down protein complexes or for tethering to solid supports during affinity purification. In the hands of synthetic chemists, it acts as a springboard for making more complex structures with bioactive potential.
Ongoing research circles around optimizing the synthesis of this molecule to avoid harsh conditions and minimize hazardous waste. One group reported a nickel-catalyzed cross-coupling method that reduces the need for noble metals, trimming both cost and environmental impact. Scientists are trying to expand the palette of possible substitutions on both the pyrazole and piperidine rings, hoping to discover new therapeutic properties. In academic settings, this molecule keeps showing up in grant proposals and high-impact publications, especially in studies aiming to understand the relationship between molecular structure and biological activity. In drug discovery, combinatorial chemistry approaches feature this molecule as a scaffold for rapid hit-and-lead identification.
As with many halogenated heterocycles, questions about long-term safety and environmental persistence keep coming up. Toxicology panels in rodents suggest the compound shows low acute oral toxicity, but there are open questions about chronic exposure. Some in vitro assays display moderate cytotoxicity at higher concentrations, an effect most pronounced in hepatocyte lines. Research keeps exploring metabolic pathways and degradation products because iodine release can impact thyroid function. Proper labeling with hazard pictograms and safety data keeps users informed, but the push for safer analogs continues. Regulatory guidelines stress the need for detailed reporting of all incidents and side effects during laboratory use.
Looking ahead, 4-(4-Iodo-1H-Pyrazol-1-Yl)Piperidine seems set for wider adoption across both industry and academia. Expansion in the radio-pharmaceutical market will likely hinge on methods for rapid, high-yield labeling. As more teams embrace AI-driven drug discovery, the compound’s structural features fit well with in silico screening pipelines, helping to identify new therapeutic targets. Environmental chemists keep a close eye on iodine-based compounds, so future iterations may feature “greener” synthetic processes and tunable degradation profiles. Spotlighting the molecule in open-access databases should help connect chemists, biologists, and material scientists, making this compound a mainstay in modern chemical research.
