Wusu, Tacheng Prefecture, Xinjiang, China admin@sinochem-nanjing.com 3389378665@qq.com
Follow us:



Dinitrosobenzene: Layered Lessons from Chemistry's Past and Future

Historical Development

Dinitrosobenzene isn’t a household name, but its story tells us a lot about how chemistry pushes boundaries. Chemists first explored nitroso compounds in the nineteenth century, driven by the hunger for dyes, explosives, and new molecules. Early efforts with nitrosobenzenes were clumsy, colored by crude reagents and limited knowledge. The understanding of aromatic substitution helped mainstream research, and Dinitrosobenzene moved into the spotlight when scientists recognized its roles as a versatile intermediate. People sometimes forget that the chemicals we debate today have roots tangled in the ambitions of old European laboratories—full of glassware, noxious fumes, and stubborn hope that every new derivative could spark industrial change.

Product Overview

Folks who work in organic synthesis often bump into dinitrosobenzene, whether they like it or not. This molecule, usually recognized for carrying two stubborn nitroso groups locked onto a benzene ring, captures attention because it’s both reactive and a little unpredictable. In lab drawers, it appears as a greenish solid, hinting at its strange electron dance. It can spook chemists with the speed of its polymerization and the sharpness of its color, serving as both a challenge and a linchpin for making new compounds. Students who wrestle with it in the lab learn quickly that it won’t allow mistakes—not if you value your glassware and your nerves.

Physical & Chemical Properties

Unpacking dinitrosobenzene’s personality starts with its structure. Sporting two NO groups, usually in the para or ortho positions, it straddles a world between stability and volatility. It doesn’t hesitate to form dimers and higher polymers—sometimes in the blink of an eye. Its greenish hue gives more clues about an electronic structure that dances with unpaired electrons. Melting points and solubility shift depending on the isomer and purity, but the compound rarely survives long in water or bright sunlight. It picks its solvents carefully, favoring organic ones like ether or chloroform, reminding us that the simplest-looking molecules can be choosy partners.

Technical Specifications & Labeling

In workplaces where precision wins the day, labels on dinitrosobenzene bottles spell out the basics: structural formula, concentration metrics, and a suite of safety warnings, since even a whiff of it can give headaches. Industrial chemists check details like molecular weight, assay percentage, and impurity profiles before opening a shipment. While regulations drift by country, responsible organizations don’t cut corners, since missing a label or misreading a purity declaration could derail an entire project. Extra care flows into packaging, since the substance can drop purity over time or under the wrong storage conditions, putting pressure on vendors to stick to their quality claims.

Preparation Method

Dinitrosobenzene doesn’t roll out of nature; it demands coaxing through careful chemical choreography. Most synthetic routes involve nitration of a benzene derivative, followed by reduction to a diamino compound, and then controlled oxidation to tack on those prized nitroso groups. The challenge lies in orchestrating the steps so the nitroso pairs land in the right spots, avoiding runaway reactions or messy byproducts. In university labs, researchers fuss over yields, while larger chemical plants weigh every variable—reaction temperatures, exacting reagent amounts, and safety hood airflow—to hold accidents at bay and crank out product at commercial scale. Some processes swap in greener oxidants out of respect for modern environmental worries, but the heart of the reaction remains stubbornly traditional.

Chemical Reactions & Modifications

Open a textbook about aromatic chemistry, and dinitrosobenzene quickly pops up in chapters about substitution and redox chemistry. It’s a gateway to azo compounds, useful as dyes and pigments, since its nitroso groups play well with amines. The dual NO groups aren’t just cosmetic—they beg to react further, sometimes stubbornly, sometimes swiftly, engaging in cyclization, coupling, and even reduction, begging chemists to nudge them in directions that suit their experiments. Industries enjoy its reactivity but curse its fickleness, since too much heat or the wrong catalyst can spin dinitrosobenzene into a tangled web of tars and oligomers. People in the lab quickly learn that planning is everything—guess wrong on a reaction condition, and you spend the afternoon cleaning brown goop off glassware.

Synonyms & Product Names

Those trying to track dinitrosobenzene through journals or patents need patience. Chemists toss around names like 1,4-dinitrosobenzene, para-dinitrosobenzene, or even p-dinitrosobenzene, depending on the source. Some older texts fold it under "p-nitrosobenzene" family, though purists wince at the ambiguity. Sometimes product catalogs list it under obscure registry numbers, leaving researchers flipping through old Merck Index volumes just to line up the right results. For the uninitiated, the various names can make literature searches a slog, but the determined chemist picks up the pattern quickly during late nights in the lab.

Safety & Operational Standards

Work with dinitrosobenzene tests a lab team’s discipline. The molecule can irritate skin and lungs in tiny quantities, forcing a culture of gloves, goggles, and double-checking air flow in hoods. The green powder stains, and the fumes sting. Handling protocols leave nothing to chance: sealed bottles, careful waste collection, and regular equipment checks. Some organizations demand periodic refresher training, especially in schools where turnover breeds inexperience. Agencies overseeing chemicals—like OSHA, REACH, and local standards bodies—shuffle paperwork to keep tabs on workplace exposure and storage, and nobody who’s spent time around the stuff questions the need. Stories abound of those who let their guard down and paid for it in discomfort or days lost to headaches and cleanup. Safety gear in labs isn’t just for show—it's born of hard lessons.

Application Area

The real world relevance of dinitrosobenzene stretches across research and industry. Its main claim to fame sits in intermediacy—chemists use it because it unlocks pathways to a swath of dyes, polymers, and specialty organics. Dye-makers value its reactivity, spinning it into colorants that stain everything from fabrics to plastics. Some scientists poke at it for polymer research, using its tendency to dimerize as a springboard for new material designs. A few niche medical and analytical tests play with its unique color shifts. Every use forces chemists to weigh convenience, cost, and risk, with some firms hunting for safer, easier-to-handle alternatives. Even with new synthetic tools on the horizon, few drop dinitrosobenzene outright, since it occupies a stubborn spot in certain specialty syntheses.

Research & Development

Academic labs keep finding fresh reasons to study dinitrosobenzene, either as a curiosity of electronic structure or a stepping stone to something bigger. Recently, interest spiked as researchers explored its role as a building block in organic electronics and optoelectronic devices. Its nitroso groups induce odd charge-transfer properties, luring teams chasing molecular switches and responsive materials. In graduate seminars, students wrestle with the quirks of its reactivity, sometimes spending months troubleshooting reaction pathways. Funding agencies and industry partners sometimes push for less hazardous analogues, but the molecule’s adaptability keeps it on the research radar. Every few years, another paper surfaces, exploring a new twist—proof that chemistry’s appetite for new reactions rarely fades.

Toxicity Research

The question of safety hangs over dinitrosobenzene like a cloud. Toxicologists have logged animal and cell studies showing negative effects on blood and nervous systems. The body’s enzymes convert nitroso compounds into reactive intermediates, raising worries over mutagenicity and chronic health impacts. In my own time around chemical safety committees, I saw teams dive deep into the nuances—asking whether risks stem from short exposures, chronic handling, or even byproducts in downstream reactions. Regulations demand low exposure, and proper engineering controls keep accidents rare. The safety conversation brings to mind the old lesson: just because something can be made, doesn’t mean it should be used without respect. Working around dinitrosobenzene demands that lesson be taken seriously.

Future Prospects

The horizon for dinitrosobenzene mirrors trends affecting all classic reagents. Industry wants greener chemistry, and that means safer, less wasteful reactions. Innovations in catalysis, cleaner oxidants, and digital reaction planning push researchers to reimagine classic molecules like this one. For now, dinitrosobenzene’s unique reactivity keeps it in the toolbox, especially for tailored syntheses in specialty materials and dyes. If a breakthrough in alternative intermediates pops up, chemists will shift quickly, driven by economics and worker safety. For students and young researchers, dinitrosobenzene stands as a symbol—a molecule shaped by the ambitions of past generations and the evolving ethics and technologies of the present. Learning its story drives home why chemical progress depends as much on wisdom as on raw invention.




What is dinitrosobenzene used for?

Understanding Dinitrosobenzene

Dinitrosobenzene sounds intimidating, but at its core, this chemical carries more value than its tongue-twisting name suggests. With its two nitroso groups hooked to a benzene ring, dinitrosobenzene looks simple on paper, yet reacts with a wide range of things in the real world. Most people don’t run across it in daily life, but those who work in chemistry labs or manufacturing plants may know it by smell and sight. Its bright green color is hard to miss.

Why Labs Value Dinitrosobenzene

Dinitrosobenzene shows up in research labs because of how it reacts during chemical experiments. Chemists often use it as a starting material when they want to build more complex molecules. From my time in college labs, I remember students using it to teach reaction mechanisms. Its structure helps students see, right in front of them, how nitroso groups behave. Schools haven’t replaced dinitrosobenzene in their organic chemistry exercises for decades since it works so reliably for teaching.

Industrial Uses Driving Demand

Industry giants rely on dinitrosobenzene in ways that most people never realize. Manufacturers include it in the process to create antioxidants. These antioxidants may go into everything from plastics to rubber, keeping products from breaking down in the sun or heat. Car tires, hoses, and shoe soles stretch further and resist cracking, in part because of chemicals made possible with dinitrosobenzene.

Textile companies also make use of dinitrosobenzene. It acts as an intermediate in the chain of reactions that result in vibrant dyes. Those deep blues and bright reds on clothing or carpets owe their long-lasting color in part to steps where dinitrosobenzene reactants help set color into the fabric. This process keeps jeans looking blue and rugs resisting fade, even after years of wear.

Research Applications Worth Noting

Scientists seek out dinitrosobenzene for more niche roles too. During polymer research, dinitrosobenzene acts as a cross-linker. This means it helps tie smaller pieces of a polymer together, which changes the resulting material’s properties. As someone who’s seen custom polymers made for medical patches or flexible electronics, I know that tweaking just one molecule early in the process affects the final strength and flexibility. Dinitrosobenzene often plays that crucial role behind the scenes.

Safety and Environmental Concerns

Dinitrosobenzene isn’t all upside. Safety matters in the lab and on the factory floor. Touching it without gloves or breathing its dust is not safe. Studies warn that dinitrosobenzene can harm skin and lungs. Proper ventilation, protective gear, and storage lock-ups reduce that risk, but human error still creeps in, especially with fast-paced production work.

On the environmental front, traces of dinitrosobenzene escaping into wastewater or soil catch attention. If left unchecked, nitroso compounds turn up in places they shouldn’t—the river, the food chain. Over the years, public watchdogs and company safety officers have pushed for more rigorous waste handling, from neutralizing chemicals before disposal to regular site inspections. Laws exist for good reason: keeping chemical leaks from harming workers and neighbors alike.

Looking Ahead: Finding Balance

Dinitrosobenzene isn’t going away. Its place in manufacturing and research keeps demand steady. But that brings the ongoing task of balancing its industrial value against health and environmental risks. Better safety training, smarter engineering, and investment in cleanup technology matter. Chemistry doesn’t happen in isolation, and neither should responsibility for its byproducts.

Is dinitrosobenzene hazardous to health?

What We Know About Dinitrosobenzene and Health

Every day we come across chemicals that sound like tongue-twisters out of a chemistry textbook, but every so often, one pops up that’s worth digging into. Dinitrosobenzene sits in that camp. The name doesn’t exactly roll off the tongue, but the impact on the body can be hard-hitting if ignored. If you work in science, chemistry, or manufacturing, you probably know these compounds don’t often get a spotlight outside the lab. Dinitrosobenzene actually refers to two isomers, but both have similar fundamental risks, because that nitroso group doesn’t mess around with human health.

What Dinitrosobenzene Does to the Body

I remember reading Safety Data Sheets and OSHA warnings for aromatic nitro and nitroso compounds. The folks putting out those documents weren’t exaggerating. Breathing in dinitrosobenzene vapors or dust means you risk acute symptoms, and nobody wants headaches, dizziness, or cyanosis hitting in the workplace. The real deal here? Dinitrosobenzene can mess with red blood cells, turning hemoglobin into methemoglobin—cutting off the body’s oxygen supply. Fingers and lips turning blue is not science fiction, that’s real methemoglobinemia knocking at the door.

Packing or handling this chemical without good gloves, goggles, or a respirator invites serious skin and respiratory irritation. I’ve talked to manufacturing staff who said they started feeling light-headed and “off” just spending a morning around open containers. Chronic exposure can cook up liver or kidney issues, and some nitroso compounds turn carcinogenic when not respected.

How Exposure Happens

Factories and research labs aren’t the only places where dinitrosobenzene might show up. Some dyes, and even explosives industries, managed to give this stuff a spot on their inventory. Accidents happen, and improper waste disposal means chemicals don’t always stay where they belong. If you live near an industrial area, groundwater or air could become a problem, especially without environmental controls. OSHA’s chipping away at workplace exposure limits for good reason. The ACGIH marked dinitrosobenzene as an occupational hazard, seeing enough cases of exposure leading to ER visits.

What Do the Experts Say?

Health bodies pull no punches on dinitrosobenzene. The CDC lists symptoms and stresses immediate removal from exposure. Most employer training drills home the point—spill kits, safety showers, protective suits. Even the best intent goes sideways if corners get cut, so safety comes down to training, culture, and regular checks. Nobody wants dinitrosobenzene showing up on their bloodwork or as the reason for a workforce’s sick days.

Taking Action: Keeping People Safe

Prevention always beats scrambling after exposure. In my years talking with safety officers, the same message comes up: personal protective equipment works only when used, ventilation systems keep air clear, and spills need cleaning without delay. Safety data tells the same story: spills and leaks happen quickly, lingering risks mount if not cleaned up.

Good reporting and traceability help figure out exposure patterns and, in the long run, nudge regulators to keep dangerous chemicals in check. For communities, strong local oversight and transparent information sharing make a difference. Nothing replaces a solid workplace safety culture built on real training and direct experience. That approach saves lives and lets everyone clock out without worrying about the air they breathe or the residue on their hands.

How should dinitrosobenzene be stored safely?

Why Storage Matters for Dinitrosobenzene

I’ve had a long relationship with chemical safety, and I’ve seen where things can go wrong when people underestimate the risks. Dinitrosobenzene isn’t something to ignore. It comes with hazards: potentially toxic, volatile, and reactive. Storing this chemical with respect and planning makes all the difference in keeping everyone healthy and the workplace running. If you cut corners, the consequences can hit fast—both for people and property.

Understanding the Realities of Dinitrosobenzene

Chemically, dinitrosobenzene reacts with heat, sparks, and strong acids or bases. If vapor or dust forms, inhaling it could mess with your nervous system. I remember a case at a small lab where a loose lid sparked an evacuation after fumes started to spread. It taught everyone firsthand: vigilance isn’t optional. Handling this chemical deserves careful attention to detail, not just routine.

Steps for Safe Storage

Locking up dinitrosobenzene ideally starts with choosing the right storage spot. Select a cool, dry area—nothing fancy, just a place away from sun or moisture. I’ve worked in labs where simple roof leaks combined with humidity turned manageable chemicals into real problems.

Containers make a huge difference. Use tightly sealed, clearly labeled bottles made of glass or compatible plastics. Avoid metals, since dinitrosobenzene can corrode some of them. It’s not about overcomplicating—just double-checking lids and labels before setting things on a shelf.

Segregation should never be overlooked. Keep dinitrosobenzene far from flammable materials, acids, and bases. One friend of mine once watched an entire shelf go up in smoke because careless storage led to cross-contamination. Fireproof cabinets made for hazardous chemicals offer reassurance. Ventilated areas prevent dangerous buildup. Simple habits like storing related chemicals together and double-bagging make the space safer.

Personal Protection and Handling

I’ve always relied on gloves, goggles, and lab coats. Splashes, spills, or even opening a container without gloves can leave a mark or cause dizziness from the fumes. Trusting in ‘it’ll be fine’ gets folks in trouble. Install eye wash stations and keep spill kits close to hand. Staff should always know where to find them—not just the safety officer.

Working alone with dinitrosobenzene is asking for trouble. I’ve always encouraged colleagues to follow the buddy system. If something does happen, help arrives faster. If someone feels faint or notices a strange color or smell, help them out of the area right away.

Labeling and Long-Term Management

Labels help everyone. Include the name, hazard warnings, and the date it was received. Rotate stock so older chemicals get used first, because expired dinitrosobenzene becomes riskier. Keep all inventory documented—half the accidents I’ve witnessed happened because people didn’t know what was really in a storage cabinet.

If you learn that a container or location can’t handle its load, call in professionals. I’ve watched cleanup crews rescue labs that thought a broken package was a small problem. They use the right gear and get rid of waste with the right protocols.

Building a Culture of Safety

Real safety lives in habits. Training matters. I believe every team, no matter the size, does better when they treat chemical safety as a group effort. Reporting leaks, changing faulty containers, and following storage rules save time, money, and lives, even if it feels routine. Practicing regular safety drills and learning from near misses brings everyone home in one piece.

What is the chemical structure of dinitrosobenzene?

Behind the Name: Dinitrosobenzene

Dinitrosobenzene doesn’t show up in daily conversation, but it speaks volumes about how chemistry shapes industry and materials science. As a compound, it roots itself in a simple concept: taking a benzene ring—the backbone of so many chemicals—and linking two nitroso groups to it. Each nitroso group (–NO) brings oxygen and nitrogen together. When you plant two of them onto a benzene ring, a chemist calls it dinitrosobenzene.

Breaking Down the Structure

Picture a hexagon: six carbon atoms, each with alternating single and double bonds—this is the benzene ring. Now, instead of imagining it as a static flat sheet, visualize two nitroso groups attached to two different carbon atoms on this ring. Most often, these groups sit across from each other, which people call the para position. That arrangement gives para-dinitrosobenzene, by far the most talked about of its forms. There’s also the ortho and meta versions, depending on where the nitroso groups stick, but the para form stands out for its stability and unique reactivity.

Why Chemists Pay Attention to This Compound

Dinitrosobenzene gets noticed not just for its symmetry but for the way it can form polymers. In the solid state, those nitroso groups reach out and connect with each other, making long chain-like structures. This unusual behavior caught my interest back in university during an advanced organic chemistry lab, where we tried to coax the bright green crystals to shift from solid to dissolved. That colour speaks to the pi-conjugation between the nitroso groups and the ring. These properties contribute to a deeper story: scientists use this compound to better understand electronic properties in materials and bond formation in organic molecules.

Importance for Industry and Research

Dinitrosobenzene’s structure underpins its value in research. Take the way it interacts with metals. The nitroso group, with its lone pair of electrons on nitrogen, allows the compound to bind to metal ions—paving the way for catalysis studies, or creating model compounds for enzyme research. In materials science, the coordination links between dinitrosobenzene’s nitroso groups offer insights for designing new polymers with electrical or optical functions.

This molecule also plays a small but influential role in dye chemistry and colorimetry. Its intense color changes serve as a clear indicator for certain reactions. During my time in an industrial lab, my team relied on the nitroso group’s visible response to track the progress of synthesis routes. That hands-on application grounds the compound’s reputation as more than a theoretical curiosity.

Moving Toward Safer and Greener Approaches

Handling chemicals built on the benzene nucleus always raises questions of health and environmental impact. Benzene derivatives, especially those with reactive functional groups, deserve real caution. In modern labs, closed systems, personal protective equipment, and green chemistry protocols protect both the experimenter and the environment. These steps matter—shortcuts and mishandling can lead to lingering hazards.

Researchers also search for alternative starting materials that provide similar reactive sites without the aromatic ring’s downsides. Advances in organic synthesis and a greater appreciation for sustainability keep shifting priorities. Striking a balance between harnessing molecules like dinitrosobenzene for their unique chemistry and keeping safety and environmental stewardship front and center shapes real lab work every day.

Where can I purchase dinitrosobenzene?

The Chemistry Behind the Question

It’s easy to look up an unfamiliar chemical like dinitrosobenzene and scroll through search results, hoping for an online retailer. Reality looks much different than shopping for a printer cartridge or some fasteners. Dinitrosobenzene belongs to a family of high-energy, potentially explosive compounds that most of us have never handled or even seen outside a lab.

Why Dinitrosobenzene Isn’t for Public Sale

People hear about lab chemicals on the news and wonder why they aren’t sold over the counter. Dinitrosobenzene, with its deep blue crystals and history as a research chemical, raises some red flags for suppliers and authorities. Most of us wouldn’t recognize the risk that comes with storing or handling this kind of substance. It reacts under certain conditions and can pose a serious safety threat. The law takes this seriously. Selling dinitrosobenzene calls for special permits. Oversight protects not only the customer but also the general public.

Gatekeeping Chemical Access—A Necessary Barrier

Looking back on my days as a lab assistant, I remember strict inventory logs and double-checked orders for any chemical outside the “safe” range. Even students needed sign-off to touch volatile compounds. The reason is clear: loss of control—whether by accident or curiosity—can end in catastrophe. Suppliers usually need evidence of legitimate business or research purposes just to consider an order. Most of these companies go through multi-step vetting. They want to know about your training, intended use, and your facility’s ability to store reactive materials responsibly. No Home Depot trip gets you past those questions.

Public Health, Security, and Ethical Responsibility

Access to high-risk chemicals brings heavy ethical issues. Letting untrained individuals buy dangerous substances would fuel accidents or worse. Big incidents in the news—industrial fires, chemical spills, and even criminal misuse—have shaped modern regulations. It’s not just about avoiding personal harm; it’s about shared safety. A single misused shipment of a compound like dinitrosobenzene can have consequences for a whole community. For companies in the chemical supply business, following these rules helps them keep their licenses, avoid lawsuits, and contribute to wider public trust.

Finding and Purchasing—What Researchers Need to Know

Researchers in need of dinitrosobenzene face a long process. Chemical suppliers only sell to legal laboratories, universities, and registered businesses. They ask for proof of legitimate use. You need documents—often purchase orders, business credentials, research plans, and local government permissions. Orders might include background checks or site visits from regulatory bodies. Reputable suppliers include Sigma-Aldrich, Alfa Aesar, or TCI America. These companies rarely engage with individuals as customers.

Safe Research, Not DIY

Most aspiring experimenters don’t get that every stage—ordering, shipping, handling, and storage—comes wrapped in legal requirements and basic ethics. If you’re not part of a registered research group or industrial operation, there isn’t an honest path to acquiring dinitrosobenzene. This isn’t about blocking curiosity or innovation. It’s about keeping everyone safe at work, at home, and in our neighborhoods.

Dinitrosobenzene
Dinitrosobenzene
Dinitrosobenzene
Names
Preferred IUPAC name 1,2-Dinitrosobenzene
Other names 1,2-Dinitrosobenzene
1,3-Dinitrosobenzene
1,4-Dinitrosobenzene
Benzene, dinitroso-
DNB
Pronunciation /daɪˌnaɪtrəˌsoʊbɛnˈziːn/
Identifiers
CAS Number [100-25-4]
Beilstein Reference 1209245
ChEBI CHEBI:28839
ChEMBL CHEMBL50480
ChemSpider 20635643
DrugBank DB13155
ECHA InfoCard 100.012.909
EC Number 202-870-9
Gmelin Reference 83257
KEGG C18808
MeSH Dinitrosobenzene
PubChem CID 7218
RTECS number DA6475000
UNII 6S93Y5PXY5
UN number 1325
Properties
Chemical formula C6H4N2O2
Molar mass 122.11 g/mol
Appearance Blue crystalline solid
Odor disagreeable
Density 1.31 g/cm³
Solubility in water insoluble
log P 1.98
Vapor pressure 0.056 mmHg (25 °C)
Acidity (pKa) 3.7
Basicity (pKb) 10.29
Magnetic susceptibility (χ) -51.4·10⁻⁶ cm³/mol
Refractive index (nD) 1.615
Viscosity Viscous liquid
Dipole moment 2.61 D
Thermochemistry
Std molar entropy (S⦵298) 253.6 J·mol⁻¹·K⁻¹
Std enthalpy of combustion (ΔcH⦵298) -187 kJ mol⁻¹
Hazards
Main hazards Toxic if swallowed, in contact with skin or if inhaled; causes skin and eye irritation; may cause respiratory irritation.
GHS labelling GHS02, GHS06
Pictograms GHS06,GHS08
Signal word Danger
Hazard statements H301 + H311 + H331: Toxic if swallowed, in contact with skin or if inhaled.
Precautionary statements P260, P264, P270, P273, P280, P301+P312, P302+P352, P305+P351+P338, P312, P330, P337+P313, P362+P364, P501
NFPA 704 (fire diamond) 1-2-2-W
Flash point 82°C
Autoignition temperature 210 °C (410 °F; 483 K)
Lethal dose or concentration LD50 oral rat 200 mg/kg
LD50 (median dose) LD50 (median dose): 250 mg/kg (oral, rat)
NIOSH DM 2455000
PEL (Permissible) 1 mg/m3
REL (Recommended) 0.1 ppm
IDLH (Immediate danger) 50 mg/m³
Related compounds
Related compounds Nitrosobenzene
Nitrobenzene
Azobenzene