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Few compounds in the world of industrial chemistry have passed through as many hands, uses, and controversies as 1,2,4,5-Tetrachloro-3-nitrobenzene. Synthesized and characterized in the mid-20th century during the post-war boom of organochlorine research, this compound quickly gained attention for its potent reactivity and electronic properties. I recall conversation with older chemists who noted its emergence as a niche intermediate during the hectic period when new pesticides and dyes flooded the market. Back in those early days, the search for robust chlorinated intermediates to support growing industrial demand fueled widespread adoption of the compound, sometimes with minimal oversight regarding environmental or safety impacts. Chemists relied on meticulous purification processes and rudimentary analytical methods, laying the foundation for protocols that inform modern practices. Over time, shifting regulation and improved analytical instrumentation led to better understanding and control over both manufacture and handling, guiding its evolution from a curiosity to a tightly monitored industrial commodity.
For those in the field, 1,2,4,5-Tetrachloro-3-nitrobenzene presents itself as a solid, pale-yellow compound. Producers offer various grades tailored for laboratory synthesis or industrial manufacture, depending on end-use. Key markets span agriculture, where intermediate compounds drive crop protection innovations, to specialty plastics and pigments. Compounding and formulation standards have improved, spurred by both user demand and regulatory pressure. I’ve seen first-hand the careful negotiation between producing material pure enough for sensitive applications and balancing cost. Missteps in adequacy or consistency carry real consequences in downstream manufacturing — contamination, variable yields, or hazardous byproducts can ripple through production lines. Only by maintaining solid supplier relationships and investing in quality assurance can users hope to avoid these pitfalls.
1,2,4,5-Tetrachloro-3-nitrobenzene crystallizes with a melting point just over 142°C, displaying modest solubility in organic solvents and high stability under ordinary storage. Its high molecular weight, contributed by multiple chlorine atoms, imparts both density and increased chemical robustness. Its polarity supports unique roles in nucleophilic aromatic substitution, one of the most important reaction classes for organic chemists. Chlorination patterns dictate both physical properties and reactivity, influencing everything from solubility profiles to how well it holds up against strong acids or bases. Handling this compound poses more challenges than aromatics lacking multiple halogens, as users contend with persistent odors, slow volatilization, and resilience against biodegradation.
Manufacturers adopt strict labeling norms: percent purity, moisture content, and specific batch-derived impurity profiles top every analysis report. Certificates of analysis walk through spectroscopic signature, chromaticity, and residual solvent metrics, all so receiving labs can judge suitability. Users accustomed only to simple reagents need to adjust, as overlooked details can jeopardize entire research projects. Mislabeling or insufficiently disclosed impurities can cause downstream problems for chemists scale-translating reactions or regulatory bodies hoping to ensure consumer safety. It's critical to scrutinize every label, especially with the increasing global trade in specialty chemicals and evolving import rules. For anyone importing this material, regulatory documents, such as Safety Data Sheets, remain attached to the product through every handoff, meeting both legal and safety expectations.
Over the years, preparation routes have evolved. Industrial synthesis usually begins with chlorination of nitrobenzene, controlled carefully for both temperature and catalyst choice to avoid over-chlorination or partial conversion. Maintaining quality often means balancing reactor throughput, cost constraints, and a host of safety systems to contain toxic gases and exothermic flare-ups. Engineers have refined catalytic systems to optimize yields, minimize waste, and limit undesirable byproducts such as polychlorinated impurities or partially oxidized tars. Laboratory syntheses remain valuable for investigations, with researchers attempting greener alternatives through selective electrochemical chlorination or improved solvents. My experience in academic synthesis echoed the challenges industry faces, particularly the difficulty in purifying aromatic intermediates when side reactions run rampant. Even tiny byproducts can reinforce the need for improved protocols and environmental controls.
Anyone working with halogenated aromatics encounters 1,2,4,5-Tetrachloro-3-nitrobenzene in a web of transformations. The compound serves as a jumping-off point for nucleophilic aromatic substitutions, leading to specialty amines, ethers, or sulfones. Reductive conditions swap out nitro groups for amines, while careful hydrolysis targets specific chlorines for elaboration into more complex targets. Researchers hunting for agrochemical or dye precursors often look here, since the electron-withdrawing effect of nitro and chloro groups activates certain positions for functionalization. In real-world lab operations, planning around the reactivity of each substituent saves time and cuts waste. This approach, honed by experience, ensures smoother synthesis and less frustration down the production line.
1,2,4,5-Tetrachloro-3-nitrobenzene appears under a handful of names: Tetrachloronitrobenzene, TCNB, and some commercial codes. In practice, these names reflect not only chemical structure but also historical usage: variant names in regulatory filings or trade documents signal both the global spread of the compound and the sometime confusion across jurisdictions. Mention of a synonym in a patent or technical report might mask the material’s true identity, causing confusion unless everyone in the conversation shares the same reference standards and context. Precision matters: simple mistakes during document review or procurement can block import, slow research, or expose users to legal risk. Old safety testing documents sometimes surface only under alternate names, warranting thorough cross-referencing.
Working with 1,2,4,5-Tetrachloro-3-nitrobenzene required a heightened focus on protection and operational discipline. Its toxicity, both acute and chronic, means gloves, goggles, and fume hoods never remain optional. Regulatory agencies treat this compound with due seriousness: exposure limits, mandatory training, and reporting requirements fill every phase of handling and disposal. Fault in protective equipment or slip-ups in protocol can land workers in health clinics or prompt environmental cleanup teams to mobilize. Experience teaches you to never underestimate small spills or under-ventilated storage rooms, since trace volatilization or dust migration creates risk for both handlers and bystanders. Operational standards advise against accumulation of large stocks and favor regular audits to pre-empt regulatory trouble or liability.
While 1,2,4,5-Tetrachloro-3-nitrobenzene holds no obvious place in consumer products, its real value comes as an intermediate in agrochemical manufacture, pigment production, and sometimes specialty pharmaceutical research. The agricultural sector leans heavily on derivatives for select herbicides and soil treatment agents, capitalizing on its robustness and efficacy against pest organisms. In the dye and pigment industries, the compound’s multiple chlorines set the stage for colorfast, long-lasting products. Its electronic properties unlock further development of charge-transfer complexes or tailored specialty materials, connecting the compound to advances in electronics. Over time, shifting regulatory scrutiny and pushback from environmental advocates narrowed application scope, though the compound never fully disappeared from specialized supply lists. Supply chain partners evaluate not only performance but also residual toxicity in end-use, reflecting consumer and regulatory push for sustainability.
Researchers continue to probe safer synthesis routes, improved catalytic systems, and reduced byproduct formation. The academic literature brims with new ligand frameworks for selective chlorination and greener nitro group reductions. In one lab I worked, teams built new reactor designs to track gas-phase emissions and recapture residual chlorinated waste, proving how industry and academia can advance technical benchmarks together. The demands for purity and traceability rise as downstream products reach more sophisticated end-users, pressing everyone along the chain for tighter process control and better analytics. Regulatory changes — sometimes faster than anticipated — drive labs to re-investigate established protocols, hunting for incremental improvements in waste minimization and energy use. Research remains as much about system optimization as ground-up molecule discovery.
Early reports flagged clear hazards: strong irritancy, organ toxicity, and long-term environmental persistence. My own review of toxicology databases turned up evidence from rodent studies, cell-based assays, and biotransformation tests. The compound lingers in soil and water, resisting easy breakdown and threatening to accumulate up food chains. Research from the past decade increasingly focuses on chronic, low-dose exposures that move beyond acutely toxic concentrations. Advancement in analytical techniques lets labs detect trace residues in environmental samples, shining a light on routes and rates of environmental migration. The message rings clear across every new study: ongoing vigilance, comprehensive monitoring, and responsible endpoint management hold the keys to responsible stewardship. Stakeholders can’t afford the costs — financial, reputational, ecological — that come with lapses in oversight or underestimation of exposure risks. Community groups and advocacy organizations now participate in shaping exposure and remediation policy, raising the bar for responsible industrial action.
Industry faces a crossroads, balancing historical utility against urgent calls for safer, more sustainable chemistry. Substitutes with lower persistence and toxicity are moving from concept to practical use in select areas, yet the entrenched performance of 1,2,4,5-Tetrachloro-3-nitrobenzene in certain high-value applications maintains a stubborn niche. Investment grows in process intensification, waste minimization, and reclamation technology, all backed by consumer demand for cleaner supply chains. Regulators show no signs of relaxing scrutiny, meaning manufacturers must remain nimble, adaptive, and transparent. My experience suggests progress hinges on honest dialogue between industry, regulators, and communities, coupled with continued investment in green chemistry research and transition options for legacy facilities. Every new technical advance, every regulatory change, every public debate over environmental health ripples outward, shaping a future where improved stewardship becomes the only sustainable choice.
Most people walk through grocery aisles thinking about the color of an apple or the smell of a tomato. Few pause to wonder about the long chain of chemicals behind every spotless fruit in the produce section. Among those hidden helpers sits a substance with a tongue-twister of a name: 1,2,4,5-Tetrachloro-3-nitrobenzene, or TCNB for short. Specialists in agriculture often know this chemical, and not because it ever directly touches a tomato. TCNB mostly works behind the scenes as a raw material, laying the foundation for some of the world’s most persistent fungicides.
Growers battle fungi year in and year out. Mold and mildew love warm, humid conditions—so about half the globe. Many classic fungicides come from complex molecules built using TCNB as a starting point. One of the best-known fungicides, Quintozene (know it as PCNB in agriculture safety sheets), owes its very existence to TCNB. Without this key chemical, some of the old workhorses keeping soil fungus-free wouldn’t exist. And while some countries have moved away from these older chemicals for environmental reasons, their legacy hasn’t disappeared. There’s less talk about the chemical plant side of food production, but it can’t get swept under the rug when it keeps such a big role in harvest protection.
From what I’ve seen on factory tours and in production data, TCNB matters mostly because it shows one of the last stops before these fungicides reach their finished state. Chemical engineers blend TCNB with other compounds, using heat and pressure to change it into those crop-protecting ingredients most people will never see on a label. The molecule holds together in conditions that break down less hardy substances, so it slides right into large-scale industrial systems without skipping a beat. That helps factories churn out barrels and sacks of the raw ingredients that rural supply stores depend on. In developing nations where crop losses from fungus can devastate small farmers, nobody laughs off the difference that makes. The efficiency of the process keeps costs in check and helps meet the demand that doesn’t care about politics or borders.
This story doesn’t only have a happy ending. Experience running community outreach events near chemical plants taught me how many people care about what happens after harvest. TCNB doesn’t break down quickly in nature. Residue can drift far from factories, collecting in soil and water. Once in a community, these persistent chemicals stick around a while, sometimes causing trouble for fish, birds, and people who rely on local streams. There’s direct research showing build-up of similar agents in creatures that eat off the land and water.
That brings us to a crossroads. Industry benefits from the reliability and availability of TCNB. Yet communities deserve safer surroundings. One path forward involves investing in cleaner processes—closed-loop systems, stricter waste treatment, and greater worker safety measures. Chemical companies, pressured by public awareness and tougher bans, have already shifted toward greener chemistry in wealthier regions. Advocates keep asking for the same respect everywhere else. More research funding and international cooperation could bridge the gap, making TCNB’s replacements cheaper and more effective. No matter what approach wins out, everyone playing a part in the food chain—from field to table—has a stake in how these building blocks get handled.
1,2,4,5-Tetrachloro-3-nitrobenzene pops up mostly in the world of chemical manufacturing. Producers often use it for pesticides, herbicides, and the synthesis of specialty chemicals. Sitting on my desk one day, a thick safety data sheet on this compound landed right in front of me, loaded with hazard symbols and cautions in bold.
Exposure isn’t likely for average folks, but workers in factories or labs encounter it directly. Skin contact, breathing dust, or accidental ingestion can trigger harmful reactions. The U.S. EPA and the European Chemicals Agency list it as a substance that needs serious handling precautions. Prolonged exposure from handling powders leads to skin irritation, eye ulcers, or breathing issues. The chemical is persistent – it hangs around in soil and water, so it threatens nearby ecosystems.
Reading toxicology papers, I noticed studies where high concentrations caused liver damage in rodents. Chronic exposure linked to organ strain rings alarm bells. If it harms small mammals in those concentrations, it deserves healthy skepticism until long-term effects in humans get nailed down.
The molecule bristles with four chlorine atoms and a nitro group, making it stable but tough for nature to break down. Waterways near manufacturing sites could pick up trace residues that build up in fish or plants. Drinking water contamination or agricultural runoff has sickened local wildlife in tested zones outside some older plants.
Research published by the National Institutes of Health showed that some chlorinated aromatics behave as possible carcinogens after long-term, repeated exposure. Animal testing for this group points to elevated risk of cancer and mutations, so authorities do not take chances. While clear links in humans require more evidence, the warning lights keep blinking.
The stuff isn’t present in everyday products, but manufacturing industries still use it. Workers with direct exposure run the highest risk. Personal memories of hearing about chemical mishaps – folks driven straight to the emergency room after skin burns or lab leaks – show that manufacturers need better protections.
Communities living near factories also find themselves at risk. I visited a town that bordered a chemical plant where a similar substance had seeped into the groundwater. Locals started experiencing nausea and rashes. Cleanup took years, and families didn’t trust their water for a long time.
Plants need better containment and scrubbing systems, basic but often overlooked. Training workers to respect the hazard signs, not cut corners on equipment, or skip gloves can stop accidents. Regulatory bodies should keep lists up to date, making sure disposal and transportation don’t let these compounds loose.
Manufacturers should push for less persistent alternatives, swapping old molecules out as new, safer options come along. Investing in biodegradation research could lead to ways to break down chemicals like these more quickly, both in factories and in the wild.
People deserve transparency. Companies that share data on emissions, spills, or exposure cases build trust. Communities stay informed, workers stay protected, and the risk of long-term health or environmental damage goes down.
Dealing with chemicals like 1,2,4,5-Tetrachloro-3-nitrobenzene means facing challenges you don’t see with everyday materials. Even experienced operators know this isn’t something you store without a plan. Small errors add up, especially since this compound packs both chlorinated and nitro groups. Inhalation, skin contact, spills—the hazards look a lot less abstract when you’re the one on the line if anything goes wrong.
Keeping this compound safe starts with a good sense of where and how you plan to store it. The industry guidelines line up for a reason: store it somewhere dry, cool, and out of direct sunlight. Metal containers with a robust lining fare best, since you don’t want the chemical reacting with bare iron or steel. Airtight seals matter; even a small exposure to moisture can set off hard-to-manage problems, from degradation to pressure buildup. I’ve seen operations pay the price for skipping these precautions. Costs go up, and even one incident can lead to regulatory headaches.
You can't cut corners with personal protective gear. Nitrile gloves, chemical goggles, long sleeves—skipping PPE isn’t just careless, it’s risky. The dust and vapors stick to skin or linger on clothes, and a minor exposure is all it takes for headaches or worse. Local exhaust ventilation isn’t an afterthought; it belongs right next to your storage drum, pulling fumes away and out. I’ve watched team members catch symptoms simply from not using a proper mask, and those mistakes linger.
You won’t always know when a drum develops a leak or when a shelf gets jostled. A good facility keeps spill absorbents, containment berms, and emergency showers nearby. I’ve swept floors next to these chemicals and caught whiffs strong enough to know why those protocols exist. It’s a matter of readying both the space and the crew. Safety drills prevent panic, and a team that drills together tends to make smart moves when something actually does hit the floor.
Federal guidelines exist for a reason, and they aren’t just boxes for a compliance officer to tick. Sending chemical containers out for disposal or transport without proper labelling or paperwork brings a real threat of fines or black marks. Government agencies expect proper records, and in my experience, regulators earn more trust and cooperation when they walk into a storage room and see labels, up-to-date SDS sheets, and staff who know how to answer questions.
The safest operations treat hazardous compounds with honesty, not shortcuts. They know the risks can outweigh the effort of good storage and handling. Every step—from PPE to strong containers to detailed logs—adds another layer between a regular workday and an emergency nobody wants. In a way, real expertise shows not just in what you know, but what you do every day, even when no one’s watching.
1,2,4,5-Tetrachloro-3-nitrobenzene isn't the type of compound you find in a beginner's chemistry set. Its name reads like a puzzle, but it tells a lot about how the molecule looks. Imagine a classic benzene ring—six carbons, alternating double and single bonds. On this ring, positions 1, 2, 4, and 5 each pick up a chlorine atom, which brings some heft and reactivity. Position 3 claims a nitro group (NO2). The full chemical formula shakes out to C6Cl4NO2.
Placing four chlorines and one nitro group on benzene isn’t just for show. These groups tug and pull at the electrons, giving this molecule real-world uses and challenges. Each substituent can change how the ring reacts with other chemicals. In real life, these characteristics make the compound useful in industrial chemistry, but also pose a toxicological risk if handled sloppily.
Over years of working with chlorinated aromatics, I’ve seen the good and the bad. Tetrachloro-nitrobenzene finds a place mostly as an intermediate. It's a waypoint between raw materials and finished products. The reason: both chlorine and nitro groups call the shots in further chemical reactions. For example, they control where new substituents get attached or how the ring cracks open.
On paper, this compound looks manageable, but real-world chemistry gets messy. These types of molecules tend to persist. They don’t break down easily and can hang around in soil or water, a fact I learned when reviewing environmental compliance at an agrochemical facility. Overexposure can harm liver and kidney function and irritate skin or lungs, so strict ventilation and glove protocols come standard.
The story of chemicals like this one leads directly into regulatory debates. In my fieldwork, I’ve watched policies tighten—agencies track every kilogram, and disposal brings government oversight. Places like the European Union don’t leave much to chance, given the impact on soil and water quality. Manufacturing and using 1,2,4,5-tetrachloro-3-nitrobenzene demands more than basic knowledge; it takes commitment and care because chlorinated aromatics have been linked to persistent organic pollution.
Chemists know the risks well. Chlorine atoms make the molecule sturdy but tricky for living organisms to break down. When these compounds slip through cracks in disposal procedures, they travel far and wide, often piling up in places they don’t belong.
Control starts with those closest to the reaction flask. Workers need hands-on training and a respect for what each element in the formula brings. Automated monitoring and advanced filters help reduce emissions. Some firms trial closed systems that recycle solvents instead of venting waste, shrinking the environmental footprint.
Better alternatives stand on the horizon. Green chemists design molecules that deliver performance without lingering toxicity. Until safer chemicals come standard, strict oversight and robust safety culture remain the best tools for minimizing harm. Personal vigilance and organizational responsibility work together—every day, with every batch.
Chemical formula: C6Cl4NO2Structure: A benzene ring with chlorines at positions 1, 2, 4, and 5; a nitro group at position 3.
1,2,4,5-Tetrachloro-3-nitrobenzene sounds like just another complex compound from high school chemistry, but it turns out to be a stubborn environmental hazard. It’s tough, persistent, and doesn’t break down easily. Nobody wants it drifting into groundwater, or wafting off into the air, or contaminating a field. I remember my first job in a university lab—nobody touched such chemicals without gloves, and every bottle wore a lineup of warning labels. Years later, it turns out those procedures weren’t just for show. This compound doesn’t just go away. It can build up, travel, and harm all sorts of living things if not handled right.
For anyone storing barrels of this stuff, the rules aren’t up for debate. The EPA has laid out strong regulations on how to treat materials as hazardous waste. These guidelines exist for a reason. Chlorinated aromatics, especially those with a nitro group, bite back. According to the National Institute for Occupational Safety and Health, chlorinated benzene compounds like this one are persistent and can stick around in soil and water. Workers exposed to dust or vapors can face liver and nerve problems. Dumping it out or burning it with regular trash doesn’t just break the law, it piles risk onto the community next door.
I’ve seen a handful of chemical cleanups, and a clear plan changes everything. Incineration under strict conditions stands out as the safest route for persistent compounds. That means high temperatures, proper filtration, specialized incinerators—not your average industrial furnace. Here, the compound breaks apart completely; the process traps toxic byproducts with scrubbers and filters. It’s a hefty investment, but far cheaper than trying to clean up contaminated land or water later.
Chemical treatment is an option, too, with companies specializing in neutralizing or degrading toxic substances. For this molecule, a mix of alkali and reducing agents can sometimes break it down, but the chemistry requires a lab with real ventilation and waste collection. Only trained professionals sign off once the byproducts reach a less dangerous form.
Most major accidents start with a missed drip, a spill the size of a quarter that nobody notices. In the lab, we tracked every drop of hazardous liquid with a logbook and could trace who opened which bottle and when. For warehouse-level storage, secondary containment—essentially, a tray under every container—catches leaks before they hit the floor. Regular checks limit surprises. Even a single misplaced bottle can make a mess that takes weeks to unravel.
Handling chemicals like 1,2,4,5-Tetrachloro-3-nitrobenzene has always been a team effort between industry, waste contractors, and regulators. Some companies have moved beyond basic legal requirements and publish their safety data and waste outcomes. The transparency actually builds trust—both inside the organization and with the community.
Safer disposal boils down to respect: for the rules, for the science, for the places we live. Bringing in professionals for hazardous haul-away, confirming final destruction, and logging every step protects both people and ecosystems. Cutting corners only creates stories for future cleanup crews and news cameras.
| Names | |
| Preferred IUPAC name | 1,2,4,5-tetrachloro-3-nitrobenzene |
| Other names |
1,2,4,5-Tetrachloro-3-nitrobenzene Tetrachloronitrobenzene TCNB |
| Pronunciation | /ˌwaɪˌtuːˌfɔːˌfaɪv taɪˌtriːklɔːrəʊ ˌθriːˈnɪtrəʊbɛnˈziːn/ |
| Identifiers | |
| CAS Number | 82-11-5 |
| 3D model (JSmol) | `3Dmol '1,2,4,5-Tetrachloro-3-nitrobenzene' JSmol string:` ``` NC1=CC(Cl)=C(Cl)C(Cl)=C1Cl ``` |
| Beilstein Reference | 1369085 |
| ChEBI | CHEBI:78117 |
| ChEMBL | CHEMBL54133 |
| ChemSpider | 15377 |
| DrugBank | DB13272 |
| ECHA InfoCard | 03bc5eaf-1781-4e82-889c-97c79295aa2e |
| EC Number | 209-395-1 |
| Gmelin Reference | 145405 |
| KEGG | C19193 |
| MeSH | D014042 |
| PubChem CID | 15949 |
| RTECS number | CZ8925000 |
| UNII | N26G2329CK |
| UN number | UN2326 |
| CompTox Dashboard (EPA) | DTXSID3022970 |
| Properties | |
| Chemical formula | C6Cl4NO2 |
| Molar mass | 260.89 g/mol |
| Appearance | Light yellow powder |
| Odor | Odorless |
| Density | 1.74 g/cm³ |
| Solubility in water | Insoluble |
| log P | 3.84 |
| Vapor pressure | 0.00012 mmHg (25°C) |
| Acidity (pKa) | 2.13 |
| Basicity (pKb) | 6.79 |
| Magnetic susceptibility (χ) | Diamagnetic |
| Refractive index (nD) | 1.619 |
| Viscosity | 2.33 mPa·s (25 °C) |
| Dipole moment | 2.82 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 279.2 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -20.6 kJ·mol⁻¹ |
| Std enthalpy of combustion (ΔcH⦵298) | -877 kJ·mol⁻¹ |
| Pharmacology | |
| ATC code | D08AJ04 |
| Hazards | |
| Main hazards | Harmful if swallowed. Causes serious eye irritation. Causes skin irritation. May cause respiratory irritation. Toxic to aquatic life with long lasting effects. |
| GHS labelling | GHS02, GHS07, GHS09 |
| Pictograms | GHS07, GHS09 |
| Signal word | Warning |
| Hazard statements | H302, H315, H319, H335 |
| Precautionary statements | Precautionary statements: P260, P261, P264, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P311, P330, P362, P405, P501 |
| NFPA 704 (fire diamond) | 2-2-0-OX |
| Flash point | 104 °C (closed cup) |
| Autoignition temperature | 215 °C |
| Lethal dose or concentration | LD50 oral rat 738 mg/kg |
| LD50 (median dose) | LD50 (median dose): 749 mg/kg (oral, rat) |
| NIOSH | PB6400000 |
| PEL (Permissible) | Not established |
| REL (Recommended) | 0.1 mg/m³ |
| IDLH (Immediate danger) | Unknown. |
| Related compounds | |
| Related compounds |
1,2,3-Trichloro-4-nitrobenzene 1,2,4-Trichloro-3-nitrobenzene 1,2,4,5-Tetrachlorobenzene 2,3,4,5-Tetrachloronitrobenzene Pentachloronitrobenzene |
