Chemists have explored cyclic amines for over a century, searching for compounds offering stability, reactivity, and versatility. 4,4'-Trimethylenedipiperidine emerged as a prominent member of this family when researchers in the mid-20th century began synthesizing dipiperidine derivatives to broaden the palette of building blocks for industrial and pharmaceutical chemistry. Early developments focused on basic amine reactivity, but curiosity about dimeric structures and bridging methylene chains led innovators to develop the trimethylene-linked variant. Much of the historical work stemmed from demands in polymer chemistry, rubber vulcanization, and specialty catalyst sectors. The need for amines with improved control over molecular spacing pushed the focus toward this specialized compound, and it grew in favor as a reliable intermediate for a range of applications.
4,4'-Trimethylenedipiperidine stands out as a diamine, combining two piperidine rings joined by a trimethylene bridge. This unique architecture supports a dual-reactive amine platform, suited for both cross-linking and chain extension routes in a variety of chemical syntheses. Industry often relies on its flexibility and robust core structure to unlock new possibilities in process engineering. From the perspective of a formulator, dealing with compounds of this type offers multiple points of reactivity and a non-aromatic backbone uncommon in many traditional amines, allowing for formulations that bridge flexibility with strength.
This compound typically appears as a crystalline solid at room temperature, with a melting point ranging in the moderate zone, aiding in convenient handling. Its piperidine rings bring decent solubility in polar and some organic solvents, suiting it to various processing environments. With two secondary amine groups, the compound can tolerate a range of reactivity conditions without breaking down, making its shelf-stability notable. Its trimethylene bridge provides a bit of flexibility, lowering ring strain compared to analogs with shorter chains. In regards to odor, dipiperidines have a characteristic amine smell, which brings back memories of undergraduate labs and the fine line between scientific curiosity and rapid ventilation.
Producers typically supply 4,4'-Trimethylenedipiperidine with specifications for purity—often above 97%—emphasizing low residual solvents and limited presence of ring-opened or oligomerized byproducts. Labels indicate its chemical structure, molecular weight (210.35 g/mol), and key identifiers such as CAS Registry Number, ensuring easy reference for researchers and compliance officers. Loosely packed, white crystals are the industry standard; bulk shipments come with specific UN numbers for safe transport, as authorities have recognized its amine nature and set guidelines for shipping and handling. SDS documents cover inhalation, contact, and emergency protocols, a reflection of how practice has led to frameworks that protect both people and property.
Synthesizing 4,4'-Trimethylenedipiperidine often starts with piperidine as the base, building up via alkylation reactions using 1,3-dihalopropane or similar agents under basic conditions to bridge two piperidine units. Catalysts and controlled temperatures help steer the reaction toward the dimer, combatting the tendency of cyclic amines to favor side reactions. Finished reactions undergo fractional distillation or crystallization, repeatedly washing away unreacted starting material and lower-molecular-weight byproducts. Such methods speak to the ingenuity of synthetic chemists, capable of guiding molecules through complex landscapes with resourcefulness and patience that have always inspired me, especially when a synthesis finally yields a crystalline product after a week of troubleshooting.
The two amine groups on the piperidine rings open the door to a series of downstream modifications. Acylation, alkylation, and sulfonation reactions apply readily, while its nitrogen centers present sites for quaternization, producing salts for specific solubility or reactivity demands. In polymer science, 4,4'-Trimethylenedipiperidine reacts with diisocyanates to form polyureas and polyurethanes, often endowing polymers with a unique combination of rigidity and flexibility. Reactivity in Mannich-type reactions or as a ligand in organometallic catalysis has been recorded in literature, and I’ve found such diverse chemistry underlines why researchers constantly return to this scaffold when other amines fall short in stability or selectivity.
The literature uses several synonyms for 4,4'-Trimethylenedipiperidine, including N,N'-Trimethylenebis(piperidine), 1,3-Propanediylbis(piperidine), and sometimes just dipiperidine for brevity. Commercial sources might list it under custom catalog numbers or alphabetic variations, but the backbone remains recognizable to those with experience among heterocyclic amines. Multiple naming conventions reflect the diversity of its supply and the lack of standardization in specialty chemicals, a small challenge I have often encountered when sourcing from different regions or catalogs.
Amine compounds invite rigorous safety checks. 4,4'-Trimethylenedipiperidine needs gloves, goggles, and proper fume hoods, due to the risk of irritation and potential sensitization after repeated exposure. Its moderate volatility demands tight storage and handling protocols, with ventilation ranking high among priorities. Waste disposal warrants neutralization and regulated capture to prevent environmental dumping, a challenge for anyone managing a busy laboratory or pilot plant. Training protocols for operational staff draw on decades of hard lessons, ensuring that even experienced chemists respect the hazards associated with cyclic amines and their derivatives.
The uses of 4,4'-Trimethylenedipiperidine span chemical manufacturing, pharmaceuticals, catalysis, and advanced polymer materials. In polymers, its role as a curing agent helps make resins tougher and more resilient—vital in coatings, adhesives, and engineering plastics. Medicinal chemistry uses it to build complex molecules where controlled amine placement is key. In coordination chemistry, the two piperidine rings serve as bidentate ligands that stabilize metal centers, enhancing catalysis or tuning activity in fine chemical syntheses. Personally, using this compound has always brought a sense of versatility; it’s the sort of thing you reach for when you need something just a bit more robust and adaptable than simple ethylenediamine.
Work on 4,4'-Trimethylenedipiperidine continues in academic and industrial labs worldwide. Researchers examine new derivatives, tailored for changing demands in green chemistry and sustainable polymer production. Ongoing efforts focus on improving yields, lowering energy inputs, and limiting hazardous side-products during synthesis. As the public becomes more conscious of environmental effects, labs focus on alternative feedstocks, enabling cleaner, more responsible production. Cutting-edge work studies functionalization of the piperidine rings to create chiral or highly selective intermediates, targeting the fine-tuning of drug candidates or catalysts. My time in research showed me the compound's flexibility, often providing that structural backbone for totally new function—one of those “yes, we can try that” moments in multidisciplinary brainstorming.
Understanding the toxicity of 4,4'-Trimethylenedipiperidine has shaped safe handling and exposure guidelines. Acute toxicity studies highlight irritation to the skin, eyes, and respiratory tract. Chronic exposure links to sensitization and, in animal models, some organ-level changes, though data remains limited compared to other industrial chemicals. Many labs now monitor exposure limits carefully, minimizing contact and using regular personal protective equipment audits. Environmental toxicity research seeks to clarify how breakdown products move through soil and water systems. The need to balance utility with safety remains a recurring topic in every chemical safety seminar, echoing the lessons of industrial mishaps and the still-unfolding story of chemical stewardship.
As chemical manufacturing evolves, 4,4'-Trimethylenedipiperidine faces both challenges and opportunities. Researchers eye it for new roles in high-performance polymers, membrane technology, and advanced battery electrolytes. Green chemistry initiatives drive efforts to derive the backbone from renewable sources, rather than traditional petrochemicals. In pharmaceutical synthesis, interest grows in exploring its chiral modifications, aiming for more precise drug development candidates. Advocacy for lower-toxicity, highly efficient intermediates keeps the focus on refining both preparation methods and industrial scale-up. I see ambitions among young chemists to loosen old paradigms, taking compounds like 4,4'-Trimethylenedipiperidine out of the shadows of specialty catalogs and putting them at the center of next-generation technologies—if science and industry keep prioritizing safety, transparency, and sustainability at every turn.
4,4'-Trimethylenedipiperidine doesn’t often show up in the headlines, but in the chemical world, it’s a workhorse. I first came across this compound working on a project with a startup focused on advanced plastics. At the time, the push was for new-generation polymers, something tougher and more flexible than the old standards. This is where 4,4'-Trimethylenedipiperidine plays a key role. In making certain high-performance materials, it steps in as a curing agent or a chain extender, connecting polymer chains and giving the finished product better strength and durability.
You can picture this compound as a kind of helper molecule, bringing other chemical components together. It isn’t splashy, but it makes products that last longer and handle heat or chemicals better. Polyamides, for example, rely on it to deliver flexibility in things like automotive parts and coatings that hold up under rough conditions. Anyone who’s had a bumper resist years of weather or a paint job that shrugs off chemicals has likely benefited from innovations tied to tools like 4,4'-Trimethylenedipiperidine.
Some stories about this chemical point to its use in pharmaceuticals, not as a main ingredient, but as a building block. Medicinal chemists like having flexible, nitrogen-containing rings during drug discovery. These rings work as scaffolds for new molecules. The piperidine group found in this compound can appear in antihistamines or antipsychotic medications, forming part of what gives these drugs their effects. There’s a lot of creativity in the pharmaceutical labs, so having a compound like this gives researchers more ways to experiment and tweak promising molecules.
Over the years, I’ve talked to teams trying to design new antibiotics. Piperidine derivatives come up in these conversations because they can sidestep resistance seen with older drugs. Some chemists see 4,4'-Trimethylenedipiperidine as a shortcut to fresh drug designs. The hard truth is it takes years to move a drug from lab to patient, but every new tool helps.
Just because something makes products tougher doesn’t mean the process ends there. Handling chemicals like 4,4'-Trimethylenedipiperidine calls for responsibility. My own experience with chemical manufacturing taught me the importance of strong safety protocols, clear labeling, and proper waste handling. Skin contact or inhalation isn’t a game—operators need gloves, goggles, and proper ventilation. Waste shouldn’t end up in the wrong place, so modern plants put serious systems in place to catch leaks and keep emissions down.
As industries look ahead, one way forward is making sure that useful chemicals like 4,4'-Trimethylenedipiperidine get handled with health and the environment in mind. Companies can invest in training and equipment for safer workplaces. Engineers designing materials or drugs can look for ways to conserve resources or reduce waste. Recycling or finding ways to reuse byproducts from the process can also make a dent. It’s not always about replacing chemicals, but about using them smarter, and that’s where collaboration between chemists, engineers, and environmental scientists pays off.
4,4’-Trimethylenedipiperidine draws chemists and manufacturers for a reason—it's not your every-day amine. Its structure sports two piperidine rings connected by a propylene chain at the 4-position on each ring. That connection matters. It offers both rigidity from the rings and flexibility from the link, which shapes how it behaves in the lab and in applications.
In the physical world, 4,4'-Trimethylenedipiperidine acts as a solid at room temperature. It usually appears as a white crystalline powder and does not carry a strong odor, making it easier to manage in a standard lab setting than some amines. With a melting point range hovering between 90 and 95 degrees Celsius, storage requirements aren’t special, but heat and direct sunlight can change its state unexpectedly. Solubility also comes into play. Water won’t do the trick—this compound dissolves more readily in organic solvents like ethanol and acetone, which fits its non-polar framework. That trait can cause problems if you try to clean up spills with water alone or plan to dissolve it in polar solvents.
The two piperidine nitrogens display typical amine reactivity. They accept protons, grab on to acids, and participate in alkylation and acylation reactions. This makes 4,4’-Trimethylenedipiperidine a handy intermediate for big-scale chemical synthesis. Companies that depend on polyamides, epoxy hardeners, or specialty pharmaceuticals often look for intermediates like this to take advantage of its reactivity and backbone structure. The secondary amine groups cut down on side-reactions and make downstream purification easier than some alternatives.
Exposure to strong acids or oxidizers can change its molecular setup or destroy the rings. That outcome brings unwanted byproducts, so it’s worth having controls and monitoring systems in place. Its chemical stability under dry, sealed conditions works in its favor for shelf life, but once you open a container, exposure to air and humidity invites trouble. Moisture can help start degradation or transformation, even if those changes run slowly.
Anyone handling this kind of amine knows that even if a powder seems harmless, skin and eye contact create risk. The literature points to moderate irritation with direct exposure and the possibility of toxic effects if inhaled or ingested in large amounts. I’ve seen too many labs overlook amine hazards—gloves, glasses, and fume hoods are non-negotiable with this compound. Accidental spills should be neutralized and gathered up, not washed down the drain. Long-term storage in airtight, labeled containers will keep things safer for everyone, and that practice deserves reinforcement with every new batch.
The world of polymers, adhesives, and drug discovery all seek stronger, more predictable intermediates. 4,4'-Trimethylenedipiperidine fills a clear gap. Firms looking to reduce production steps or streamline purification often land on compounds with this kind of backbone, where efficiency improves both cost and yield. On the research front, finding greener solvents or processes to cut down on hazardous waste should stay a priority. My experience says small improvements in how a compound is used or handled can shift the whole process from risky to reliable, keeping both workers and the environment out of danger.
4,4'-Trimethylenedipiperidine does not show up on every average person’s radar, but it pops up in a lot of industrial work. Folks working in labs and factories run into this one since it helps make plastics, coatings, and sometimes acts as a curing agent. Information about it demands proper attention, especially for employees who handle it. If you’ve stood on a concrete floor where resins or specialty polymers get produced, you’ve likely seen a big drum labeled with chemical names you’ve never thought about twice. This is one of those chemicals that may seem “background,” yet its risks deserve a closer look.
Data about 4,4'-Trimethylenedipiperidine suggest some irritation to skin and eyes. Tests in animals report short-term harm, especially if a splash hits the eyes or spills land on bare hands. Some evidence points to possible irritation of the respiratory tract, especially in settings where dust or fumes get in the air. The substance doesn’t carry a well-known reputation for causing cancer, and long-term studies in humans come up short. Still, its structural relatives sometimes show more serious effects, and that makes it smart to treat with care.
Workers in factories rely on up-to-date knowledge about the materials they handle. Far too many stories exist where folks didn’t get the full picture, or they learned about the downsides after a few decades of regular contact. I remember touring a plant where most workers wore gloves and goggles, not just for the big drum chemicals but even for solutions mixed at low concentrations. It’s not just about following the rules; protecting skin and lungs isn’t optional. Even substances listed as “mild irritants” can bring lasting problems with enough exposure.
Simple safety steps help a lot more than they seem. Glove use and protective eyewear block most common routes of exposure. Good ventilation takes care of the rest. Field reports show that accidental splashes, not inhalation, cause most of the issues for this chemical. Most manufacturers supply detailed safety data sheets, and those deserve close reading. Reporting symptoms early—itchy skin, watery eyes, or sore throats—can mean the difference between a minor irritation and a bigger problem down the line.
Every industry using chemical intermediates owes its workers clarity and honesty about hazards. Something that starts out as a “mild irritant” can become a chronic issue for someone working day in and day out. A savvy operation runs regular training, makes safety data sheets easily available, and encourages open talk about exposure or spills without blaming the worker.
Ongoing research remains essential. Gathering real human data—beyond short-term studies in mice—will help answer open questions. Government agencies and independent labs should keep pressing for results that matter to workers, not just paper reports designed for compliance. The real value shows up when someone clocks out after decades in the business and walks away healthy.
Chemicals like 4,4'-Trimethylenedipiperidine can’t be dismissed or sensationalized. Respect, accurate information, and practical safety steps reduce risk. Quick action after exposure, honest reporting, and steady research all make a difference on the factory floor and beyond.
Anyone who's spent time working with chemicals knows that comfort in the lab often comes down to respecting what you’re handling. 4,4'-Trimethylenedipiperidine isn’t a household name, but its role in industrial and research settings deserves attention. Experience teaches that handling any organic amine requires thinking practically and accepting the risks involved. Eye, skin, and respiratory irritation often catch newcomers off guard if they drop their guard even for a minute.
Reports and safety data sheets describe this compound as a corrosive, meaning contact with your skin or eyes can end in pain and possibly permanent damage. I've seen coworkers miss a single glove check and learn it the hard way: a trip to the safety shower is nobody’s favorite memory. The fumes tend to creep up, so working in a well-ventilated fume hood doesn’t feel optional. Proper storage and handling take the uncertainty out of the equation—and they start with a real, worn-in respect for the hazards involved.
Many laboratories treat storage as an afterthought, stuffing bottles where space allows. That sort of approach spells trouble fast with reactive materials like this one. I’ve learned to check humidity and temperature in the storage area. Keep this amine cool and dry; dampness or heat only increases the risk of decomposition or slow reactions over time. All it takes is a leaky air vent or an undetected drip to spoil entire stockpiles.
The container matters as much as where it sits. High-density polyethylene or glass with an airtight seal blocks out moisture. I've seen rust from stray water vapor leach under loose caps and ruin otherwise perfect batches. If the label wears off or jars look too similar, the risk grows; clear labeling fuels good habits and avoids mix-ups on busy mornings.
My first year in chemical research taught me more from cleanup drills than anything else. Spills do happen—sometimes the bottle tips, sometimes a splash sneaks under your goggles. Thinking ahead can turn a potential disaster into just an inconvenience. Keeping mineral oil or spill absorbent close by, along with running an eyewash station test weekly, makes all the difference. I make sure everyone in the lab remembers where to find and how to use a neutralizing solution that works well with organic amines.
Vigilance with personal protective equipment creates a buffer between a routine transfer and a dangerous mistake. Nitrile gloves hold up longer than latex, and safety goggles beat prescription glasses every time for splash protection. Wearing a lab coat with closed sleeves takes five seconds; those who’ve rushed through the ritual mostly come to regret it eventually.
Trust in colleagues and your own consistency matters as much as the science itself. Peer-checks before pouring or weighing keep missed steps rare. Proper waste labeling keeps risk in check long after the day’s work finishes. Reliable documentation keeps future handlers safe, whether that’s months later or the following week.
Safety culture doesn’t take shape overnight, but it sticks when everyone steps up and shares stories, both the close calls and the best practices. The right steps for storing and handling 4,4'-Trimethylenedipiperidine seem simple enough once you live them daily. Practical respect for the hazards at hand keeps accidents out of the headlines and research moving forward.
Sourcing fine chemicals like 4,4'-Trimethylenedipiperidine takes more work than pulling up a generic supplier list. The players active in this market carry real weight, not only because of their reach but due to reputation built on quality and trust. Over the past decade, China’s chemical sector has landed a dominant position, especially in specialty raw materials for pharmaceutical, polymer, and specialty coating applications. Names like TCI Chemicals, Alfa Aesar, and Merck/Sigma-Aldrich continue to anchor the global catalog supplier space, each offering this compound in research and industrial scales.
Manufacturers on the production side in China—such as Wuhan Yuancheng Gongchuang Technology and Suzhou Vosun Chemical—factory-produce this compound, sending shipments worldwide. India’s Anhui Wotu Chemical and Hefei TNJ Chemical also meet both local and export demand. European and American labs may rely on stacking supply chains, but most raw manufacturing happens in Asian facilities where labor, logistics, and regulatory hurdles align for low overhead.
Experience dealing with specialty chemicals has taught me that reliable sourcing isn’t just a luxury. Years ago, one missed shipment meant a full project delay at my former lab—those lost weeks cost money and credibility. Ensuring that regulatory paperwork and purity are as promised matters, especially for fine intermediates like 4,4'-Trimethylenedipiperidine, which serve as links in pharmaceutical or materials development. Suppliers like Sigma-Aldrich or Alfa Aesar are popular partly due to their strong documentation and quality assurance standards.
Lower-cost producers can tempt a buyer looking to meet a budget, but surprise contaminants or batch inconsistencies too often offset whatever is saved upfront. Counterfeit or poorly handled chemicals from vague brokers have flooded markets before, putting not only the end product at risk but also intellectual property and safety.
The chemical industry faces tighter global regulatory scrutiny. Legitimate producers catalog product information, safety data sheets, compliance certificates, and lawful uses before shipping. I’ve seen researchers forced to chase non-existent safety data or import documentation when a shipment arrived missing any sort of paperwork—huge waste of resources. Companies like Merck, TCI, and Alfa Aesar invest heavily to stay ahead here.
The best way to secure quality chemicals is to use trusted international suppliers—those with a long track record, strong third-party reviews, and thorough documentation. For those scaling up to commercial quantities, it’s smart to build direct relationships with original producers. Periodic site audits, third-party samples, and transparent quality checks can keep things honest. Regulators recommend running due diligence, verifying licenses, and tracking every link of the supply chain—from the original factory to your loading dock.
The harder clients push for cheap deals from unproven brokers, the bigger the headaches when shipments stall, products fail, and accountability disappears. It pays to learn from collective industry experience: prioritize transparency, documentation, and the kind of service that respects both science and regulation every step of the way.
| Names | |
| Preferred IUPAC name | 4,4'-Trimethylenebis(piperidine) |
| Other names |
4,4′-Trimethylenedipiperidine 1,1′-Trimethylenebis(piperidine) Trimethylenebis(4-piperidine) Bis(4-piperidyl)methane |
| Pronunciation | /ˈfɔːr fɔːr traɪˌmɛθ.ɪˌliːn daɪ pɪˈpɪrɪdiːn/ |
| Identifiers | |
| CAS Number | 2293-99-6 |
| 3D model (JSmol) | `3D model (JSmol)` string for **4,4'-Trimethylenedipiperidine**: ``` CC1CCN(CC1)CCCN2CCC(CC2)C ``` |
| Beilstein Reference | 1863783 |
| ChEBI | CHEBI:515064 |
| ChEMBL | CHEMBL71110 |
| ChemSpider | 11118109 |
| DrugBank | DB08964 |
| ECHA InfoCard | echa.europa.eu/information-on-chemicals/infocards/100.117.138 |
| EC Number | 207-953-8 |
| Gmelin Reference | 108141 |
| KEGG | C19111 |
| MeSH | D014286 |
| PubChem CID | 11864598 |
| RTECS number | TZ9625000 |
| UNII | 0D27395A35 |
| UN number | UN2810 |
| CompTox Dashboard (EPA) | DTXSID0034607 |
| Properties | |
| Chemical formula | C13H26N2 |
| Molar mass | 199.36 g/mol |
| Appearance | White to light yellow solid |
| Odor | amine-like |
| Density | 0.97 g/mL at 25 °C (lit.) |
| Solubility in water | Miscible |
| log P | 0.53 |
| Vapor pressure | 0.17 mmHg (25 °C) |
| Acidity (pKa) | pKa = 10.10 |
| Basicity (pKb) | 3.38 |
| Magnetic susceptibility (χ) | -72.0e-6 cm³/mol |
| Refractive index (nD) | 1.516 |
| Viscosity | 14.8 mPa·s (25°C) |
| Dipole moment | 2.61 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 322.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -77.6 kJ·mol⁻¹ |
| Std enthalpy of combustion (ΔcH⦵298) | -4997.7 kJ/mol |
| Pharmacology | |
| ATC code | Not assigned |
| Hazards | |
| Main hazards | Causes skin and eye irritation. Harmful if swallowed. Causes respiratory tract irritation. |
| GHS labelling | GHS05, GHS07 |
| Pictograms | GHS05 |
| Signal word | Warning |
| Hazard statements | H302, H314 |
| Precautionary statements | P260, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362+P364, P403+P233, P405, P501 |
| NFPA 704 (fire diamond) | 1-3-0 |
| Flash point | Flash point: 138°C |
| Autoignition temperature | AUTOIGNITION: 332 °C |
| Lethal dose or concentration | LD50 oral (rat) 660 mg/kg |
| LD50 (median dose) | LD50 (median dose): 400 mg/kg (oral, rat) |
| NIOSH | Not established |
| PEL (Permissible) | PEL (Permissible Exposure Limit) for 4,4'-Trimethylenedipiperidine: "Not established |
| REL (Recommended) | Not established |
| Related compounds | |
| Related compounds |
N-Methylpiperidine 1,4-Piperazinediethanesulfonic acid Piperidine Dipiperidine Trimethylenediamine |
