Benzoquinone N-chloroimine appeared on the research scene during the mid-20th century, when chemists started pushing the limits of what quinones could do in synthesis. People kept trying new ways to attach functional groups to aromatic cores, hoping for handle points that could change reactions, especially for applications in dye and pesticide chemistry. N-chloroimines came from this period as researchers in both academic and industrial labs ran into limitations with old oxidants and needed compounds that worked under milder, controlled conditions. Over decades, the focus shifted from basic methods to targeted applications, as teams realized N-chloroimines showed more than just reactivity—they had surprising selectivity in organic transformations. Years of crowded blackboards and glassware filled with orange-brown slurries turned into patents and process diagrams, each one slowly making benzoquinone N-chloroimine easier to obtain in a usable state.
Benzoquinone N-chloroimine stands out as a pale yellow to orange solid, recognized both for its reactivity in organic chemistry labs and its unpredictable behavior under certain conditions. It rarely shows up on shelves at general chemical suppliers, but specialist catalogs keep stock for those who request it. Researchers trust its presence for oxidative cyclizations or halogenations, knowing that one molecule can trigger a cascade of changes in structure when paired with electron-rich phenols or anilines. The material’s quirky shelf life, especially once exposed to moisture, reinforces why proper storage and handling matter much more than the safety data sheets let on.
Benzoquinone N-chloroimine usually forms powder or crystalline chunks, faintly aromatic but with a whiff of chlorine. It tends to break down in light and in the presence of reducing agents, making amber bottles and refrigerators standard practice. Its molecule gives a balance between oxidizing power and nitrogen reactivity, blending the electron-hungry ring of a quinone with the sharply electrophilic N–Cl group. Melting points can dip well below those of parent quinones—pure material melts around 80–90°C, sometimes decomposing instead of liquefying if the sample has impurities. Unlike many other chlorinated organic compounds, its solubility reaches comfortably into most polar organic solvents, but it resists water, avoiding hydrolysis for a time before snapping apart into hydroquinone derivatives and free chloramine.
Chemists who order benzoquinone N-chloroimine get batches graded for purity (customarily above 97%) with a detailed certificate of analysis. The fine print always calls out potential isomeric impurities stemming from alternative substitution, urging customers to confirm identity by thin-layer chromatography and NMR. Material Safety Data Sheets flag the compound as an irritant and an oxidant, listing relevant UN numbers for shipping but also special codes for temperature-sensitive material, reflecting the risk profile for transport and storage. Labels note specific lot numbers for traceability, mandatory in both pharmaceutical research and regulated manufacturing, since even a half percent of unknown side-products can scramble outcomes in precision chemistry.
For those who make it themselves, the route to benzoquinone N-chloroimine follows a straightforward logic: start with para-benzoquinone, blend with aqueous ammonia, and introduce chlorine gas or a sodium hypochlorite solution under cool, dark conditions. Stirring this mixture leads to an immediate color change—subtle burgundy shifting to ochre, then the formation of a pale precipitate. Extraction with organic solvents, followed by careful drying, isolates the crude product. Most chemists purify the product with fractional crystallization or column chromatography, since incomplete chlorination leaves behind ammonium salts and over-chlorination can produce dangerous by-products. Hardened synthetic chemists keep sidearms and gas traps at the ready during these steps. Mishandling the reaction introduces real risk, as both chlorine gas and the product itself can irritate skin, eyes, and lungs.
Benzoquinone N-chloroimine performs as both an electrophilic and a nucleophilic partner in a range of transformations. This Janus-faced behavior underlines why it keeps drawing attention in organic schemes. It introduces nitrogen into aromatic systems, facilitates dehydrogenation, and triggers ring contractions, often under milder conditions than classical chlorinating agents. It reacts with nucleophilic reagents—amines and thiols jump on the N-chloro group—populating molecules with new bonds in one flask. As a building block, it takes center stage in preparing complex heterocycles and functionalized aromatics, and chemists keep finding extensions for this behavior, such as tandem oxidation-coupling reactions.
This molecule parades under several nicknames in the world’s chemical literature. You’ll find ‘p-benzoquinone N-chloroimine,’ ‘4-chloroimino-1,4-benzoquinone,’ and in some cases, just ‘N-chloroiminoquinone.’ Regional catalogs and old German patents trot out names that combine those roots, but the thread remains: a quinone stitched to a nitrogen-chlorine fragment. Whenever possible, research teams still include the CAS number in correspondence to clear up naming confusion between derivatives.
Handling benzoquinone N-chloroimine takes a measured approach. Lab professionals wear gloves and goggles, not out of habit but from experience—solid or dust form causes irritation and best practices stop short of letting anything fly off the spatula. Fume hoods stay at full draw while weighing or reacting the compound, as offgassing can accompany warming or contact with acids. Protocols advise quick clean-up in case of spills, since slow exposure can degrade resin benchtops or corrode metal fixtures. Dispose of remains according to local laws, but most labs neutralize residues with reducing agents before transfer, avoiding any surprises in communal waste streams.
Few chemicals spark as much experimental curiosity as benzoquinone N-chloroimine—research into its uses stretches across dye manufacturing, agrochemical development, and the synthesis of biologically active aromatics. Teams looking for novel oxidation patterns in drug discovery explore its unique ability to introduce nitrogen into aromatic backbones, saving steps compared to lengthy, multi-stage syntheses. It has popped up in methods for making advanced intermediates in pigment and pharmaceutical synthesis, especially where the usual oxidants or chlorinating agents produced low yields or unwanted by-products. Its role as a coupling agent for special classes of heterocycles continues shifting new generations of reactions from dream to routine.
Current research looks to tame the reactivity of benzoquinone N-chloroimine and push it into new transformations. By combining it with transition metal catalysts, groups have found new ways to add value to simple aromatic precursors. Journals feature improved protocols that swap out corrosive gases for safer, scalable chlorinating agents, bringing more students and industrial chemists into the process. Those with an eye on process chemistry keep testing greener solvents and flow systems, reducing waste and hazard. As my own research circle discovered, dozens of side reactions lurk in the margins, but every successful run brings new mechanistic clues, like why certain substituents make a reaction fly, and others stall completely.
Benzoquinone N-chloroimine is no harmless reagent. Studies report moderate to high acute toxicity, with rapid breakdown into potentially harmful fragments under acidic, basic, or hot conditions. Chronic exposure data remain limited, but every sign points to careful limitation and substitution where practical. Toxicology screens show oxidative damage in cell models, while environmental breakdown research explores the fate of both the parent compound and its nitrogenous by-products in soil and water. Lethal dose studies on small mammal models show risk at relatively low parts per million, amplifying calls for improved ventilation and waste treatment in facilities using these materials at scale.
Benzoquinone N-chloroimine’s future looks tied to advances in selective organic synthesis and process safety. Chemists push to unlock reaction pathways that preserve its benefits but cut down on side reactions and hazardous by-products. Synthetic methods that use electricity, light, or gentle oxidants might soon replace chlorine-based steps. There’s excitement around linking this compound to polymer and material science, exploring its application in creating custom surfaces or smart coatings that respond to redox signals. Meanwhile, computational chemists run simulations trying to predict new mechanisms before the next surprise shows up at the bench. The next big step depends on deeper mechanistic work and tighter links between bench chemistry and industrial demand, as both sides hunt for better yields, cleaner processes, and improvements in worker safety. Those in the trenches know the challenges, but also see how every technical advance opens a fresh set of promising questions for the future.
Benzoquinone N-Chloroimine rarely pops up in everyday language, but this compound packs a surprising punch in the research world and industry. With its distinct structure, it becomes a stepping stone in the journey from basic chemistry to applications reaching medicine and materials science. Once you dig into its chemical profile, you see why so many researchers keep coming back to it.
I remember spending late nights in the lab trying to synthesize molecules using a range of intermediates, and Benzoquinone N-Chloroimine held a special spot. Its lability means it reacts well with nucleophiles and a range of amines, which opens doors for more creative synthesis. Chemists use it to assemble complex aromatic frameworks. Some of the brightest minds make use of its reactivity to design pharmaceuticals with unique biological activity. A study from 2022 found that derivatives of this compound showed promising inhibition against certain bacterial pathogens, giving hope for more targeted antibiotic development.
In drug discovery, chemists don’t just look for any starting material. Benzoquinone N-Chloroimine often fills that niche for constructing heterocyclic scaffolds—those familiar ring structures in many drugs. You find this sort of chemistry in action during lead optimization, when researchers adjust the molecular structure of a potential drug to sharpen its effect or shrink its toxicity. Some anti-inflammatory agents and kinase inhibitors begin their life with a reaction involving Benzoquinone N-Chloroimine. Open any peer-reviewed journal focused on synthetic medicinal chemistry, and you’ll see references to these compounds acting as both reagents and intermediates.
Organic pigments have decades of history, and innovative researchers keep hunting for new coloring agents that outlast sun and moisture. Benzoquinone N-Chloroimine gives color chemists a stable base that resists fading. Using it, pigment manufacturers tailor-make bright colorants for printing inks and plastics. It’s not rare to find patents that mention its use in the synthesis of new azo dyes, which deliver rich reds and yellows without breaking down in sunlight. People rarely think about the chemistry in their magazines or art supplies, but synthetic chemists and engineers working with these colorants rely on such building blocks to improve performance while keeping toxic byproducts in check.
Benzoquinone N-Chloroimine doesn’t just stick to old-fashioned organic chemistry. My colleagues often talk about its potential in materials research, especially where new resins and advanced polymers are needed. As polymer science races ahead, the need for monomers with unique reactivity and compatibility grows. Researchers test this compound for improved cross-linking in specialty resins, especially where durability, flexibility, or chemical resistance matter. This can mean stronger adhesives or coatings that keep machinery running longer in harsh conditions. In many ways, the quest for more reliable materials leads right back to inventive uses for molecules like Benzoquinone N-Chloroimine.
With such lively chemical behavior, there’s no room to slack on safety. Proper training, ventilation, and personal protection gear are the norm. As companies shift focus toward greener chemistry, safer alternatives get tested and approaches continue to evolve. Regulatory reviews help keep accidental exposure in check, but each chemist I know respects just how much innovation rests on putting safety first. Balancing progress and responsibility means not just chasing new discoveries—but building them on solid ground, one careful experiment at a time.
Benzoquinone N-chloroimine brings together the backbone of a quinone and the unique characteristics of an N-chloroimine group. Its chemical formula, C6H4ClN O2, reflects a six-carbon aromatic system with two oxygen atoms, a nitrogen attached to a chlorine atom, and four hydrogen atoms lining the core ring. Visualizing this, you see a benzene ring with carbon positions 1 and 4 bonded to oxygen atoms through double bonds, making it a para-benzoquinone. At position 2 or 3, a nitrogen bonded to a chlorine—an N-chloroimine group—swaps out a typical hydrogen, adding a reactive site that matters in both organic synthesis and the development of advanced materials.
Structurally, it stands out due to its functional groups. Para-benzoquinone itself reacts with nucleophiles and serves as a key building block in lab chemistry and industry. Swapping a hydrogen for an N-chloroimine changes the reactivity. The N-chloroimine group, consisting of a nitrogen double-bonded to the benzoquinone ring and single-bonded to a chlorine atom, sits on the aromatic backbone. This group can engage in reactions not possible for plain benzoquinone, including exchange reactions that swap the chlorine for new groups or generate radicals under certain conditions.
Let’s put this in context for those working in a lab or industry. If you imagine drawing it out, you start with the ring common to many aromatic compounds. Double bonded oxygens face each other at the ends of the six-sided ring. Then, off one of the carbons, the nitrogen connects directly, which holds a chlorine atom, hanging off the ring. This feature draws a chemist’s eye, since it can trigger transformations driving the synthesis of dyes, pharmaceuticals, and agrochemicals.
Personal experience in organic synthesis drives home the importance of small changes to molecules. Adding an N-chloroimine group doesn't just alter a formula on paper; it reshapes the tool kit for chemical reactions. This group can serve as a platform for creating new bonds, breaking old ones, or building complex heterocycles that end up in everything from cancer drugs to new polymers. Research points to similar derivatives acting as key intermediates in metal-catalyzed reactions, oxidative transitions, and building nitrogen-containing aromatics that crop up in crucial pharmaceuticals.
Analytical chemists look for structural clues: NMR and IR spectroscopy show clear shifts thanks to the electronegativity of chlorine and unique nitrogen bonding. These help confirm the structure in a real, usable sample—not just a theoretical sketch. Studies in the last decade highlight the use of benzoquinone derivatives for constructing pharmacophores and agricultural actives that impact millions worldwide.
Handling N-chloro compounds requires care. The added chlorine can bring sensitivity to light, heat, and moisture, with risks in air and during storage. Synthesis using standard chlorination sometimes yields mixtures, not always the clean single product needed in research. Improved methods, perhaps leveraging milder reagents or greener solvents, stand on many chemists’ wish lists. Teams worldwide share data on reaction pathways, pushing for reproducible yields and safer procedures.
From my work, the demand for characterization doesn’t end once you make the compound. Team members often invest as much effort confirming purity and identity as they do synthesizing the molecule itself. Accurate, verified structures let new discoveries move from bench to bench, lab to field, with confidence and safety.
Benzoquinone N-chloroimine, through its carefully engineered structure and blend of reactivity, will keep finding its way into advanced applications. Its chemistry highlights how one tweak opens doors in science and industry, making the understanding of both structure and formula central to progress.
Benzoquinone N-chloroimine doesn’t show up on the front page of most lab manuals, yet anyone who’s spent time with organic chemicals knows some names deserve a bit more respect than others. Here’s a compound that reacts not only with metals or acids, but can also go south if someone forgets the basic storage rules. Mishandling could spell trouble for both researchers and the facility. OSHA and the ACS list many lab injuries that could have been avoided with a bit of foresight—often it comes down to following thoughtful storage routines.
My first experience working with reactive imines involved half a dozen glass vials, a noisy fridge, and a colleague who always left notes about chemical shelf-life. Moisture always spells risk with these substances. Benzoquinone N-chloroimine doesn’t differ: it reacts easily, so any hint of ambient humidity could lead to break-down or even release gases nobody wants to breathe. A desiccator—nothing fancy—does a solid job. Standard freezers get too cold and shelves collect dust and humidity, so a dedicated fridge around four degrees Celsius hits a sweet spot for daily use. I once watched a careless storage job ruin a whole batch of imine within a week; chemists remember that bitter smell long after it’s gone.
Too much light can degrade some chemicals without anyone noticing, leaving compounds less reactive or giving off byproducts. For Benzoquinone N-chloroimine, using amber bottles or wrapping containers in aluminum foil gives a cheap but effective barrier against the lab lights. The stability doesn’t last if someone stores it near vibrating equipment, or if staff slam the fridge door too often. Movement loosens caps, and something as minor as a cracked seal might encourage slow leaks. Keeping bottles upright in a locked, labeled box will prevent most accidents before they start.
If someone sets up storage without proper labels, confusion creeps in. Anyone who’s cleaned out a crowded lab fridge recognizes the mess—sticky tape labels, faded handwriting, mystery vials. Benzoquinone N-chloroimine demands a hazard sticker, name, and re-dated inventory every time the bottle gets topped up or portioned out. Safety also comes through segregation: storing this chemical away from acids, bases, or reducing agents keeps the risk of accidental reaction low. I’ve seen too many close calls from storing reactive imines next to bleach or peroxides. These mistakes sometimes seem trivial until the day they aren’t.
Access makes a difference. Only trained researchers should have keys to storage areas. Training means more than reading a safety data sheet—it means knowing what to do if a bottle leaks or a spill lands on the bench. Every chemical fridge should have spill kits nearby, stocked with absorbent pads and the proper neutralizers. It’s worth checking if the local fire marshal and hazardous waste team know what sits in storage; minutes count during a crisis. I always remind new hires to tour the emergency showers, eyewash stations, and learn the route for chemical disposal before their first solo shift.
Trust forms when a team builds routines around double-checking storage, updating logs, and calling out the small problems before they grow. Minor checks—like replacing worn-out seals, confirming the fridge temp, or updating logs—do more for safety than the fanciest equipment. Labs that prioritize these details keep both their work and their people safe. Science deserves no less.
Benzoquinone N-chloroimine pops up in laboratories, drawing interest from researchers in organic chemistry. This compound doesn’t get discussed in the news much, but its dangers deserve real attention, especially for anyone using it in research or industrial settings.
Contact with benzoquinone N-chloroimine brings trouble. Skin may develop redness or blisters. The eyes react fast, often leading to severe irritation or, in some cases, eye damage if splashed. Small accidents turn big quickly when safety gear isn't part of the routine. Adding to the worry, inhaling dust or fumes from this compound can trigger coughing, shortness of breath, and chest tightness, much like exposure to chlorine gas. It doesn’t stop at symptoms—over time, lungs can sustain lasting injury with repeated exposure.
The true issue lies deeper. Benzoquinones don’t just irritate; some interact directly with proteins and DNA inside cells. Animal studies have raised red flags about the ability of compounds in this family to disrupt normal cell functions. Some quinones create free radicals, which damage tissue and stir up inflammation. These injuries don’t heal overnight if exposure continues.
Research published in Chemical Research in Toxicology highlights that related para-benzoquinones can act as mutagens, increasing risk for genetic mutations. While direct, long-term human studies with N-chloroimine are rare, the warning from structurally similar compounds rings loud—don’t take chances.
Health problems show up in industrial workers exposed to benzoquinone and related chemicals. Reports in occupational medicine journals document headaches, dizziness, respiratory distress, and skin disorders in people working with these chemicals without adequate protection. Small spills degrade air quality swiftly, spreading risk to anyone nearby. Most companies stick N-chloroimine in the "handle with gloves and goggles only" category, for good reason.
Disposal creates another hazard. Benzoquinone N-chloroimine lingers in soil and water, resisting easy breakdown. Wildlife, especially fish and smaller aquatic animals, show toxic reactions at relatively low doses. One study in Environmental Toxicology showed significant harm to algae and invertebrate populations exposed to related compounds at just parts-per-million. These environments struggle to recover once contaminated, spreading the risk from lab to larger ecosystems.
Trained chemists step up protection by investing in proper ventilation, fume hoods, and personal protective equipment. The value of regular safety training can't be swept aside; researchers remember stories from mentors about accidental splashes or forgotten masks. Following strict protocols saves lives, lowers exposure, and reduces contamination outside workspaces.
There’s another angle: research groups push for safer replacements. Green chemistry teams dig for compounds providing similar reactivity, but with less risk for the lungs and skin. Regulators, including the EPA and EU REACH, often tighten restrictions or demand clearer labeling. Modern chemical catalogs list clear red and yellow warnings for Benzoquinone N-chloroimine, a move that improves awareness and reduces accidents. It pays to check safety data before use rather than after trouble hits.
Safe handling and up-to-date knowledge hold the key to protecting people and the environment from benzoquinone N-chloroimine. Balancing curiosity with respect for risk ensures innovation doesn't come at too high a price. Each well-labeled bottle in the chemical cabinet and each story shared about close calls shapes a safer science culture.
Some chemicals aren’t lined up on the shelves of every supply house. Benzoquinone N-chloroimine falls straight into this group. Only the big academic or industrial labs ever seem to need it, and those who don’t work in synthetic organic chemistry rarely hear its name. There’s a reason for that. This compound is pretty specialized and doesn’t get ordered with the same ease as, say, sodium chloride.
Let’s get practical. Large international suppliers like Sigma-Aldrich, Alfa Aesar, and TCI handle most research-grade products. You might run into Benzoquinone N-chloroimine listed among their catalogs, but the story doesn’t stop there. Some reagents are “listed for inquiry only.” I’ve reached out and heard them respond, “Not in stock” more than I care to remember. Cutting-edge research drives the production and sale of chemicals like this; suppliers keep an eye on demand, and compounds with limited application show up less frequently. Procurement usually requires direct negotiation, sometimes long lead times, or even minimum quantity contracts that could scare off small research groups.
Synthesizing N-chloroimines isn’t a weekend project. It calls for skilled handling, well-controlled reaction conditions, and a proper understanding of the compound’s safety risks. Benzoquinone N-chloroimine doesn’t fall into the category of “drop-ship tomorrow.” Safety, shelf stability, and regulatory controls play into who can actually sell or ship this chemical. As a result, major countries restrict its import or internal handling, especially if it finds a use as a precursor to other sensitive or regulated chemicals.
Price also ties into availability. Costs rise not just from production but from handling, safety data paperwork, and shipping. I’ve seen offers for some rare reagents from niche firms in China, India, or Europe, each with their own trust hurdles. In these cases, buying isn’t as simple as a click and a payment. It means checking for certification, verifying lab testing, and even digging into supplier backgrounds to make sure you’re not walking into a scam or regulatory headache.
Academic labs often deal with these supply headaches by collaborating across institutions. Networks of researchers sometimes have small stashes or access through international partners. I’ve been in group meetings where someone announced, “Our friends at X University just shipped us a sample.” These relationships can matter more than any supplier’s web listing. If official routes look slow or impossible, some teams even look into small-scale in-house synthesis—though that choice brings its own risk, and it only suits those with facilities, experience, and solid safety procedures.
While chemistry advances, so does the complexity of sourcing. Improved transparency among suppliers and industry-standard authentication tools can weed out subpar and risky offers. Legal frameworks at the national and international level continue to tighten; these rules intend to keep labs, environments, and workers safe but also extend the wait for niche products. Direct partnerships between universities and trusted chemical vendors create more consistent pipelines, helping to avoid unvetted “gray market” options.
Keeping a research project on schedule means adapting to these hurdles. Teams need to stay knowledgeable about sourcing best practices: always request proper documentation, confirm the legitimacy of suppliers, and maintain compliance with local and international regulations. As chemistry pushes into ever-more sophisticated territory, supply chains have to keep pace without losing their commitment to safety and reliability.
| Names | |
| Preferred IUPAC name | (E)-1-chloro-1-imino-2,5-cyclohexadiene-1,4-dione |
| Pronunciation | /ˌbɛn.zəʊ.kwɪˈnəʊn ɛn ˈklɔːr.oʊɪˌmiːn/ |
| Identifiers | |
| CAS Number | 23995-37-3 |
| Beilstein Reference | 1101191 |
| ChEBI | CHEBI:138532 |
| ChEMBL | CHEMBL2106076 |
| ChemSpider | 31938319 |
| DrugBank | DB07917 |
| ECHA InfoCard | 06b87e5d-93ec-4be7-8006-dc6f01f5d7fd |
| EC Number | EC 257-869-2 |
| Gmelin Reference | 116132 |
| KEGG | C18619 |
| MeSH | D017975 |
| PubChem CID | 166675 |
| RTECS number | OM4552000 |
| UNII | HX5M9B6N9P |
| UN number | 3352 |
| CompTox Dashboard (EPA) | DTXSID0021698 |
| Properties | |
| Chemical formula | C6H4ClN1O2 |
| Molar mass | 191.59 g/mol |
| Appearance | Yellow solid |
| Odor | pungent |
| Density | 1.35 g/cm3 |
| Solubility in water | Slightly soluble |
| log P | 1.26 |
| Vapor pressure | 2.7 mmHg (25°C) |
| Acidity (pKa) | 6.76 |
| Basicity (pKb) | 2.74 |
| Magnetic susceptibility (χ) | -75.4 × 10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.654 |
| Dipole moment | 2.50 Debye |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 163.8 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -8.2 kJ/mol |
| Pharmacology | |
| ATC code | D03AX10 |
| Hazards | |
| GHS labelling | GHS02, GHS06, GHS08 |
| Pictograms | ClN=C1C=CC(=O)C=C1=O |
| Signal word | Danger |
| Hazard statements | H302, H315, H319, H335 |
| Precautionary statements | P280, P261, P271, P305+P351+P338, P337+P313, P301+P312, P330, P501 |
| NFPA 704 (fire diamond) | 2-3-2-ox |
| Flash point | Flash point: 79°C |
| Lethal dose or concentration | LD50 oral rat 200mg/kg |
| NIOSH | Not listed. |
| PEL (Permissible) | Not established |
| REL (Recommended) | 10-30°C |
| IDLH (Immediate danger) | IDLH: 50 ppm |
