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2,5-Dimethylaniline: Chemistry, Challenges, and Possibilities in Perspective

Historical Development

Back in the age of coal gas lighting, chemists started to dig into the lengthy list of compounds one more ring away from basic aniline. The methylated versions of aniline popped up soon after that—the 1800s saw organic chemists putting methyl groups onto benzene rings just to see how it would change things up. 2,5-Dimethylaniline grew out of this curiosity, a mere tweak, yet it brought with it fresh properties that broadened the scope for dyes, pharmaceuticals, and flavors. Its roots trace back to those early German dye firms that bet big on coal tar and its wild catalogue of amine-rich compounds. As the chemical industry moved through the 20th century, labs everywhere kept drawing on this molecule for everything from synthetic colors to starting materials in more complex chemical constructions. Today, large-scale manufacturing runs with much tighter controls, but the underlying interest in what a dimethylaniline can do hasn’t faded at all.

Product Overview

To a working chemist, 2,5-dimethylaniline means more than a chemical formula—it's an aromatic amine that finds itself on the workbench for all sorts of reactions. Most would recognize its sharp, sweet smell and the yellowish tint that often signals a bottle has been open a little too long. It finds its way into the nitty-gritty of creating specialty dyes, agrochemicals, and pharmaceutical proofs-of-concept. For folks in research, its physical profile—liquid at room temperature, floats just under water, lighter than one might guess by its molecular heft—makes it manageable yet potent enough to warrant respect. Whether you’re just running a classic coupling reaction or pushing towards more ambitious heterocycle synthesis, this compound’s flexibility makes it a useful piece in the toolkit.

Physical & Chemical Properties

This molecule brings a fairly straightforward set of properties. Its melting and boiling points park in that happy middle ground for organic solvents—high enough for stability yet not so stubborn as to foul up a distillation. That twin methyl arrangement, snug at the 2 and 5 positions on the ring, tunes its reactivity—those methyls shield it a bit from harsh attacks but keep enough of that aniline punch for classic organic transformations. Typically, handling means you’ll notice its oily consistency and its robust, lingering odor. Key to working with it is understanding how those methyl groups nudge reactivity—electrophilic substitutions get a boost, alkylations happen predictably, and one can usually count on those amine lone pairs to keep their wits about them in a range of pH values.

Technical Specifications & Labeling

Chemists expect reliable specifications, not only for reproducibility but also for safety and regulatory tracking. A clean sample shows up as a clear to light yellow liquid, and for those who dig into the numbers, the molecular formula is C8H11N. Physical constants like melting near 6°C and boiling somewhere above 200°C underpin both storage and use in the lab. Proper labeling goes well beyond the basics—a bottle must spell out toxicity, warning about skin and respiratory irritation, and remind handlers of the amine’s stubborn tendency to stick to skin and various pipettes. Each bottle ought to display clear hazard pictograms and risk phrases that truly spell out what one risks by underestimating it.

Preparation Method

On the synthetic side, routes to 2,5-dimethylaniline usually start with robust organic frameworks. Direct methylation of aniline rarely delivers the selectivity synthetic chemists demand, so most practical approaches build from the benzene ring up. Industrially, nitration of xylene followed by reduction steps in careful sequence can get you to the target—those methyl groups are steered into place before introducing the amine, which helps with both yield and purity. In a small lab, one can sometimes do it with modern palladium catalysis, trimming steps and waste, but the tried-and-tested route through xylene and careful stepwise amination sets the standard. No matter the approach, the aftermath requires serious cleanup—residual acids, metallic dust, and stubborn side products all crop up and have to be handled responsibly.

Chemical Reactions & Modifications

Aromatic amines like 2,5-dimethylaniline offer a playground for substitution chemistry. The aniline core allows for diazotization, which cascades easily into azo dye formation. This property underpins its biggest historical leap into the colorant sector; for decades, its derivatives gave new shades to textiles and inks. In a pharmaceutical setting, those methyls tweak reactivity just enough to suggest new intermediates for active molecules. Oxidation comes easy if you’re not careful—leaving a sample open to air can darken its color as it picks up oxygen. If you’re after a knack for N-alkylation or acylation, this compound obliges, opening pathways for more complex building blocks. In the hands of a diligent chemist, it also serves as a decent starting point for ring closures or heterocycle formation, though purity always demands attention.

Synonyms & Product Names

For anyone bouncing between lab catalogs or scientific papers, 2,5-dimethylaniline pops up under a handful of names. It's sometimes called 2,5-xylidine—a name rooted in the old convention of calling methylbenzenes “xylenes.” Other times, one runs into listings that label it as 2,5-dimethylbenzenamine, ensuring clarity for formal chemical classification. Keep an eye open for product names in dye or chemical supplier lists, where trade names can obscure the identity—cross-referencing the CAS number can cut through any confusion for those who want to be certain of what’s inside the bottle.

Safety & Operational Standards

Spend enough time in a laboratory and you’ll hear stories about underestimated aromatic amines. Dimethylanilines demand gloves, goggles, and respect for fume hoods. The vapor and liquid can irritate both skin and lungs; overexposure edges into acute toxicity. Eye exposure can sting fiercely, and repeated skin contact leads to redness or worse. Environmental systems in big plants capture and treat emissions—rarely is a loose bottle left open for long. Waste needs proper neutralization and incineration since amine byproducts can push through water systems and cause damage to aquatic organisms downstream. Folks working with this compound keep emergency protocols posted and seldom take chances with poorly vented spaces.

Application Area

In practice, industries tap 2,5-dimethylaniline for its utility in dye chemistry—especially for colors needing subtlety and persistence on fabric. Specialty pigments and inks pull from its structure, as the two methyl groups help nudge the hue away from standard aniline shades, pushing boundaries on colorfastness. Agrochemical researchers use it for herbicide and pesticide scaffolding, tweaking molecular recognition via the methyl groups’ electron-donating nudge. Medicinal chemists look to build future drug candidates, slipping the molecule into more complex pharmacophores that treat disease at the molecular level. Even with modern alternatives, the breadth of scenarios calling for this specific dimethylaniline keeps it on the order sheets for companies ranging from textile producers to biotech startups.

Research & Development

The research horizon rarely stands still, especially in fields built on small tweaks to molecular structure. Chemists keep probing novel modifications to the aromatic ring, exploiting the utility of dimethylanilines as anchors for new bond formations. Emerging studies tease out how minor changes on the ring can change biological properties—offering a route to more selective therapies or more persistent crop treatments. Analytical R&D leans on better detection methods, harnessing mass spectrometry and chromatography to spot trace levels in waste streams or products. Meanwhile, greener synthesis approaches try to cut down on energy and solvent use, aiming for cleaner routes and fewer byproducts, a response to the tightening regulations over chemical residues in both water and soil.

Toxicity Research

Fresh data keeps reshaping views on dimethylaniline toxicity. Animal studies document its risk profile, showing neural and liver sensitivity after exposure over time. Modern toxicology takes into account not just acute effects, but low-level, chronic impacts—including carcinogenicity and environmental persistence. New reports track breakdown pathways through soil and water, highlighting how this compound sometimes lingers instead of breaking down cleanly. Regulatory researchers push for tougher workplace limits and broader environmental monitoring to minimize long-term risks. This pressure prompts chemical makers and labs to revise protocols and invest more in waste treatment.

Future Prospects

Looking ahead, the dual pressures of innovation and sustainability shape the destiny of compounds like 2,5-dimethylaniline. On one hand, new synthetic avenues—like catalysis powered by renewable energy or biotech-based approaches—could ease the environmental cost of making these molecules. Rising demand in advanced materials, therapeutic development, and specialty dyes ensures continued interest, but debates over safety and environmental release remain sharp. Companies that can integrate safer handling methods, recover byproducts, and report clearly on risk will have the best shot at staying above regulatory hurdles. For researchers, every new use case comes bundled with a fresh responsibility—design greener, safer pathways so that chemistry can move ahead without tripping over its own environmental footprint.




What is 2,5-Dimethylaniline used for?

Diving Into 2,5-Dimethylaniline’s Real-World Uses

2,5-Dimethylaniline pops up often in industrial chemistry. Companies use it to make dyes, inks, and pigments. If you’ve ever come across brightly colored plastics or vibrant printer ink, there’s a fair chance one of the raw materials behind those colors involved chemicals like this one. The chemical structure of 2,5-Dimethylaniline adds stability and depth to color formulations, making it useful for products that need to last and maintain their color in harsh conditions.

Foundation for Agricultural Chemicals

Chemists tap into 2,5-Dimethylaniline when developing certain pesticides and herbicides. As food demand keeps climbing, farms rely more on safe and effective ways to protect crops. This compound helps form the backbone of modern agrochemicals that fight off pests without as much risk to the plants themselves. Researchers have shown that methylated anilines often serve as the building blocks for more advanced, less persistent pesticides—ones that don’t pile up in the soil or water like some older options.

The Pharmaceutical Link

People rarely consider how intermediates like 2,5-Dimethylaniline influence the medicines they take, but the pharmaceutical sector calls upon this chemical to help build active pharmaceutical ingredients (APIs). Take pain relievers and antifungal agents, for instance—producers transform the compound through several reactions, turning it into something completely different that goes into tablets and ointments. A single small molecule, if produced and handled with care, can help improve or even save lives once it becomes part of a new drug. On the flip side, concerns about impurities and toxicity show the ongoing need for precision in chemical manufacturing.

Synthetic Chemistry’s Workhorse

For those with hands-on lab experience, 2,5-Dimethylaniline often comes up during the synthesis of organic compounds. Graduate students and industrial chemists appreciate that it enables functionalization—the process of nudging molecules into the shapes and behaviors needed for specialty materials, new therapies, and even advanced polymers. The versatility brings options for creative solutions in everything from electronics to environmental clean-up materials. The real challenge comes down to controlling the hazards associated with aromatic amines. Labs need effective ventilation and rigorous handling protocols, as some forms can irritate the skin and respiratory system, or linger in the environment when not disposed of properly.

Safety, Environmental Impact, and Solutions

Manufacturing centers that use aromatic amines face scrutiny, both from regulatory bodies and local communities. 2,5-Dimethylaniline requires careful storage, handling, and disposal. Spills, leaks, and airborne emissions draw concern because aromatic amines have links to health and environmental risks. Companies that invest in closed systems, proper training, and waste treatment cut down on these risks. The Responsible Care initiative within the chemical industry highlights companies that set the bar on safe handling and transparency, encouraging others to follow suit.

For many of us, understanding how these chemicals show up in everyday life means trusting manufacturers, researchers, and public agencies to keep a close watch over production and use. Continued investments in green chemistry help reduce risks, since newer processes rely on less hazardous materials and make it easier to recycle or safely destroy waste.

There’s no end in sight for the usefulness of compounds like 2,5-Dimethylaniline, but smart management ensures that their benefits don’t come at a cost to people or the planet.

What are the safety precautions when handling 2,5-Dimethylaniline?

Knowledge Is The First Barrier Against Accidents

2,5-Dimethylaniline isn’t a term you hear at a family barbecue, but in labs and factories, it’s right there on the labels. This organic compound plays a role in dye production and chemical synthesis. With its usefulness comes a level of risk. I’ve spent enough hours in research labs to see what happens if safety shortcuts get taken with aromatic amines like this one. Eyes water, lungs sting, someone scrambles for the safety shower—every mistake drives home the lesson: knowing the hazards is step one.

Personal Protective Gear: Not Just For Looks

Colleagues often joke that goggles and gloves make people look like mad scientists, but these jokes fade quick when the chemical spills. 2,5-Dimethylaniline can irritate skin, eyes, and respiratory passages; there’s also evidence that prolonged or repeated exposure may harm organs. Always pull on nitrile or neoprene gloves. Cotton won’t cut it. A lab coat? Absolutely—preferably one that resists splashes. Eye protection needs to wrap snug, because vapors drift and tiny droplets land in the worst possible places. In stuffy rooms or with bigger volumes, go with a face shield or even a full respirator if ventilation doesn’t keep the air clear.

Ventilation Shouldn’t Be An Afterthought

Good air flow isn’t just about comfort. 2,5-Dimethylaniline gives off vapors, and breathing those in can be trouble. Fume hoods exist for a reason—and they always stay on, even for a quick weigh-in or pour. I’ve seen poorly ventilated rooms turn an otherwise simple task into a hazardous situation. Local exhaust keeps those vapors away from lungs and eyes. For anyone handling this chemical outside a controlled lab, extra attention goes to window fans and air exchanges. Never let the smell linger—if you can smell it, it’s in your system.

Storage Isn’t An Afterthought

Leaving open bottles around invites disaster. Always seal containers tightly, label them clearly, and store them away from food or drink. I’ve run into problems when someone stored an aromatic amine in a fridge meant for lunches. That’s a recipe for contamination and accidental poisoning—never forget that chemicals find ways to travel and mix, especially liquids. 2,5-Dimethylaniline belongs in a well-ventilated, cool, dry spot, away from strong acids or oxidizers.

Preparedness Saves The Day

Spills happen fast. Labs without spill kits and absorbent pads invite chaos. Water and soap might sound like enough, but these only work if nearby and used immediately. Make sure every workspace has access to eyewash stations, safety showers, and clear emergency procedures. I carve out ten minutes at the start of a project to walk through nearest exits and emergency gear—it isn’t lost time, it’s insurance against panic.

Smart Choices Protect The Team

Working with 2,5-Dimethylaniline isn’t about fearing chemicals. It’s about respect. Every mistake costs real health, and that sticks with a person well after the beakers get washed and put away. Sharing what works, learning from close calls, and keeping up with safety data sheets help everyone keep all their fingers and their peace of mind. That sense of shared responsibility means no shortcuts, no guesswork, and more time focusing on what matters: the work, and the people doing it.

What is the chemical structure of 2,5-Dimethylaniline?

Structure and Function in Everyday Chemistry

Learning about the chemical backbone of 2,5-Dimethylaniline reveals a lot about how science touches real life. This aromatic compound brings together an aniline core — that’s a benzene ring linked to an amine group (NH2) — with two methyl groups attached at the 2 and 5 positions on the ring. Chemically, its formula stands as C8H11N. Drawing this on paper, you’d see the benzene hexagon, the amine group leaning off carbon number one, and two methyl branches, each sticking out of carbons two and five. Looking closer, those methyl attachments tweak how electrons move around the ring, which changes what this molecule can do compared to plain aniline.

Real-World Chemistry, Not Just Lab Theory

In practice, 2,5-Dimethylaniline gets a lot of use outside the textbook. Its structure allows it to join in reactions that help make dyes, pharmaceuticals, and pesticides. Dye makers like using it because the methyl groups affect which wavelengths of light get absorbed, which means a wider palette. Pharmaceutical chemists pick it up to build more complex molecules. They value that amine group for forming bonds, and the methyls for shaping how new medicines interact inside the body. That is not just academic. The choices made in the lab often impact things like colorfastness in textiles or the stability of medicine on a shelf at the pharmacy.

Health, Environment, and Safety

With compounds like 2,5-Dimethylaniline, the details of the structure don’t just stay on the chemist’s bench. How it reacts, the products it forms, and how it breaks down matter for workers in factories and the people living nearby. These anilines can irritate eyes, skin, or lungs, and some related compounds even carry cancer risks if exposure goes unchecked. I’ve seen how handling chemicals safely—using good ventilation, gloves, and knowing emergency wash procedures—makes all the difference. Factories must set limits. Regulators, like the US Environmental Protection Agency, keep lists and set standards, relying on research of exactly how molecules like these behave.

Smart Steps and Safer Substitutes

That doesn’t mean society gives up on useful chemicals, but it does mean we get smarter about risk. Designing safer synthesis routes matters. For 2,5-Dimethylaniline, adopting greener solvents or using fewer toxic reagents during manufacture can trim down hazards. Some companies look for alternative compounds that give similar results, so dye or drug results do not mean health headaches later. Monitoring in wastewater or emissions helps curb contamination. I’ve talked to small business owners who want to innovate, but they watch for regulations around compounds like these, keeping their eyes open for both safety and new opportunities.

Underlying Lessons from the Lab

Understanding 2,5-Dimethylaniline starts with looking at where the atoms sit, but it ends up reflecting bigger stories about chemistry’s place in life. Every small tweak to a molecule’s shape can ripple out—to products, jobs, safety, even the regulations that guide industry. Recognizing the real-world impact of these structural details means chemistry isn’t locked away in a textbook; it is part of every product on the pharmacy shelf or bolt of cloth on the rack.

How should 2,5-Dimethylaniline be stored?

Understanding What You’re Handling

I’ve seen chemical storage go wrong because of underestimating the small stuff. 2,5-Dimethylaniline doesn’t always stand out to newcomers into a lab or workshop, but anyone who’s spent enough time working with aromatic amines knows these liquids need respect. This chemical usually shows up as a yellowish oil with a sharp odor, and even a whiff makes it clear you shouldn’t treat it casually. Science shows its vapor irritates your nose and throat and can cause skin rashes if your gloves have holes or aren’t chemical-resistant. There’s more; breathing this stuff too long can hit your nervous system. I remember a co-worker with a mild headache—nobody thought much of it until the Material Safety Data Sheet spelled out how easily exposure creeps up.

Right Containers, Right Seals

In practice, storage starts with the vessel. Glass bottles with tight screw caps or sealed metal drums usually do the best job. Plastic sometimes works, but some forms degrade or become brittle over time. I once saw a plastic lid crack in a warm storeroom during summer. A single spill meant days of cleaning, and a faint odor lingered for weeks. Glass or specialized metal containers hold up far better unless you expect extreme physical knocks. Any container should close tightly to keep vapors in and water out. Moisture triggers slow reactions that foul the chemical and sometimes lead to pressure build-up—something as simple as a bad gasket can cause headaches later.

Away from Heat, Sparks, and Sunlight

This chemical reacts with strong oxidizers and acids, sometimes in violent fashion. I’ve read stories, and once saw the aftermath, of a mislabeled cabinet where incompatible bottles sat together. Label errors lead to costly and risky mistakes. Store 2,5-Dimethylaniline far from those hazard zones. Regular room temperature does fine, and you want a dry spot with solid ventilation. Direct sunlight can slowly break down the chemical and make storage containers brittle. So, a clear rule—never put this on a windowsill or near heaters, even for a day.

Personal Safety and Labeling

In my experience, clear labeling and frequent checks limit almost every major risk. Write the full chemical name, date of purchase, and hazard warnings in legible print. Color-coded stickers help stop any mix-up in busy storage rooms. Smaller labs sometimes skip regular checks, which invites trouble. If crystals or odd discoloration show up in the bottle, treat it as a red flag. Most of the accidents I’ve heard about started with someone ignoring a small change in appearance or missing label details. It’s worth pulling out bottles every few months to check for leaks, corrosion, or anything odd odorous. Dispose of old or unused chemicals according to hazardous waste regulations—environmental fines or health risks easily outweigh replacement costs.

Training and Emergency Prep

No storage guide works unless everyone involved understands the stakes. New workers and students need frequent reminders on glove selection, eye protection, and spill cleanup. In my time managing a facility, tales of “quick fixes” usually turned into major cleanups. We hung spill response sheets at eye level in the storage room and ran drills twice a year. Nearby eyewash stations, chemical showers, and handy spill kits can keep an accident from escalating. Local emergency numbers belong on every wall when dealing with chemicals like this.

Better Storage, Fewer Regrets

Every accident I’ve seen came down to missed details—loose caps, fading labels, or bottles left next to strong acids. Experience in a busy lab drilled into me that safe storage isn’t about fancy cabinets or high-end gear. It’s about never taking shortcuts, giving chemicals like 2,5-Dimethylaniline their own space, and updating labels the moment you spot damage. The right habits mean you go home at the end of the day with nothing to worry about—and no lingering chemical odor on your hands.

What are the potential health hazards of 2,5-Dimethylaniline exposure?

Why 2,5-Dimethylaniline Matters to Health

2,5-Dimethylaniline shows up in the chemical industry as a building block for dyes, pharmaceuticals, and pesticides. With its regular appearance in manufacturing, many workers and nearby residents bump into it without realizing. Even though it mostly shows up in tightly controlled settings, leaks and accidents turn a lab problem into a real-world danger. Having spent time in communities with chemical plants down the street, I’ve seen the health worries chase people long after a bad smell finally clears up.

Direct Damage: Toxins with Teeth

Skin contact causes itching, rashes, and sometimes even deeper burns. If this stuff makes its way into lungs, it irritates the airways and stings the throat, nose, and eyes. Shortness of breath and headaches become regular complaints. Beyond the surface, the real risk runs deeper—2,5-Dimethylaniline attacks the blood. It changes the hemoglobin, messing with your body’s ability to move oxygen around. This sets the stage for methemoglobinemia: people turn blue, get dizzy, and struggle to catch their breath even if they’ve just walked up a short flight of stairs. I’ve listened to folks in chemical towns describe these odd symptoms, only to figure out months later that a leak from a tank was to blame.

Long-term and Wide-ranging Effects

Long shifts around this chemical can weigh heavy on the body. People exposed for months or years say memory slips and trouble focusing start to creep into daily life. Science backs them up—animal studies show an increase in liver and kidney problems, and red blood cell breakdown. Certain animal test results point towards higher cancer risks, though the evidence for this in humans is still unfolding. What’s clear: repeated, low-dose exposure chips away at health in a way that’s hard to pin down until it’s too late.

Communities at Risk and Worker Safety

Laws in places like the United States and Europe set exposure limits, but enforcement often comes down to budgets and local resolve. In job sites where safety gear sits unused or training cuts corners, danger spikes. I’ve watched supervisors brush off complaints to hit production quotas. The real-life cost lands on workers and families living near plant fences. Kids miss school from nosebleeds; older residents go to clinics with chest pain no one can quite explain. Companies may say community monitoring is strong, but talking to neighbors reveals worries about smells and mystery dust on porch furniture.

Better Protection Means Fewer Nightmares

Stronger rules make a difference, but they only matter if people at every level care and take action. On-the-ground safety drills, regular air testing, and honest reporting help keep exposure in check. I’ve seen local groups push for regular soil tests and independent audits, which gets results when people band together. Safer alternatives exist for some uses—pushing industries toward less toxic chemicals reduces everyone’s risk. Real change starts with transparency: open records, community meetings, and workers who can speak out without fear of losing their jobs. Only then do lesson learned in one factory help others before trouble starts.

2,5-Dimethylaniline
2,5-Dimethylaniline
2,5-Dimethylaniline
Names
Preferred IUPAC name 2,5-dimethylbenzenamine
Other names 2,5-Xylidine
2,5-Dimethylbenzenamine
2,5-Dimethylphenylamine
Pronunciation /tuː,faɪv-daɪˈmɛθɪlˌæniˈliːn/
Identifiers
CAS Number 95-78-3
Beilstein Reference 1209225
ChEBI CHEBI:28690
ChEMBL CHEMBL15324
ChemSpider 12141
DrugBank DB14150
ECHA InfoCard 100.043.071
EC Number 205-500-4
Gmelin Reference 8579
KEGG C01577
MeSH D016053
PubChem CID 7309
RTECS number BY5425000
UNII IZL57XD6OI
UN number UN2239
Properties
Chemical formula C8H11N
Molar mass 121.18 g/mol
Appearance Colorless to yellow liquid
Odor amine-like
Density 0.920 g/mL at 25 °C
Solubility in water slightly soluble
log P 1.8
Vapor pressure 0.16 mmHg (25 °C)
Acidity (pKa) 4.52
Basicity (pKb) 10.77
Magnetic susceptibility (χ) -70.2·10⁻⁶ cm³/mol
Refractive index (nD) 1.560
Viscosity 3.22 cP (25°C)
Dipole moment 1.37 D
Thermochemistry
Std molar entropy (S⦵298) 174.0 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) 72.6 kJ/mol
Std enthalpy of combustion (ΔcH⦵298) -3536 kJ/mol
Pharmacology
ATC code D06BA05
Hazards
Main hazards Harmful if swallowed, in contact with skin or if inhaled. Causes skin irritation. Causes serious eye irritation. Suspected of causing cancer. May cause damage to organs through prolonged or repeated exposure.
GHS labelling GHS02, GHS07, GHS08
Pictograms GHS07
Signal word Warning
Hazard statements H302, H311, H331, H315, H319, H372, H412
Precautionary statements P261, P280, P302+P352, P304+P340, P312, P405, P501
NFPA 704 (fire diamond) 2,2,0
Flash point Flash point: 109°C
Autoignition temperature 540°C
Explosive limits 1.1–6.6%
Lethal dose or concentration LD50 oral rat 1750 mg/kg
LD50 (median dose) LD50 (median dose): 1750 mg/kg (oral, rat)
NIOSH SN 52500
PEL (Permissible) Not established
REL (Recommended) 25 mg/m³
IDLH (Immediate danger) 100 ppm
Related compounds
Related compounds 2,5-Xylidine
2,3-Dimethylaniline
2,4-Dimethylaniline
2,6-Dimethylaniline
3,4-Dimethylaniline
ortho-Xylidine