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N,N-Diethylaniline: Chemical Insights and Real-World Impact

The Journey from Discovery to Industry

N,N-Diethylaniline walks a path that reflects the broader story of chemical progress over the past century and a half. A compound born out of 19th-century experimentation with coal tar derivatives, it first gained traction because researchers saw unusual color reactions that sparked their curiosity. The dye boom in Victorian-era Europe drove chemists to isolate molecules like this for textile production, with N,N-Diethylaniline offering a stepping stone from crude mixtures to cleaner, purer products. Early researchers—often working without today’s safety precautions—set the groundwork for everything from coloring fabric to synthesizing antiseptics, not always knowing the risks they faced. The growth of the synthetic dye industry owes a lot to basic amines like this, as each new molecule carved a path for more complicated, reliable pigments and chemicals to follow.

Basics Beyond the Beaker

Anyone who spends time in a chemical lab knows the importance of analyzing a substance with a mix of caution and appreciation. With N,N-Diethylaniline, the clear, oily liquid stands out for its strong, fishy odor and its ability to dissolve well in typical organic solvents. Its boiling point, clocking in well above water, means the substance hangs around in flasks and reactors long after some more volatile partners have evaporated. Its molecular structure gives it a stubborn, oily feel that influences how it blends with other reagents and holds on to its own stability under moderate temperatures. Recognizing these characteristics isn’t just about following a checklist—years of spilled chemicals, mistakes, and careful notes have taught chemists when a new compound might surprise, especially one that carries an amine group this active.

Technical Realities and Label Clarity

Clear documentation on N,N-Diethylaniline matters on the shop floor and in academic research alike. Manufacturers stick to technical sheets that talk about purity, residual solvents, and water content, because one batch’s tiny impurity might throw a whole run of dye production off-kilter. Labels sometimes list other amines that could sneak in during production, since the process rarely produces a compound in perfect isolation. Regulations aim to set minimum thresholds for impurity levels—government agencies know that accidents and mislabeling often start with overlooked details. What ends up on a drum or bottle tells trained chemists how cautious they need to be, as even trace impurities from the synthesis stage can alter performance or safety outcomes in the next manufacturing step.

Methods Behind Production

Techniques to make N,N-Diethylaniline have barely changed in essence, though automation and better containment have trimmed risks. The classic route involves heating aniline with diethyl sulfate or similar alkylating agents, always keeping a watchful eye for runaway reactions. My own early missteps with reactions like this—overestimating glassware size, underestimating exotherms—taught me quickly how a safe process on paper can turn risky when scaling up. Keeping the process contained, scrubbing fumes, and recycling byproducts helps industrial actors both lower costs and mitigate harm to workers. Seeing these steps play out in real plants shows how much know-how sits beneath what appears to be a simple chemical process—one small error or contaminated batch can cascade through a supply chain.

Chemical Reactions and Pathways

The reactivity of N,N-Diethylaniline gives it a flexible role in organic synthesis beyond its heritage as a dye intermediate. Its nitrogen center welcomes various transformations—oxidation, coupling, and even the occasional electrophilic aromatic substitution, making it a useful workhorse in synthesis. For researchers developing novel molecules, the challenge comes from controlling where the next transformation lands. Messy side products can gum up equipment or mess with reaction yields. From firsthand experience, tweaking ratios, reaction times, and even stirring speeds can shift outcomes just enough to take experimental chemistry from frustrating to successful.

Other Names on the Label

The chemical trade often complicates things with its jumble of synonyms. N,N-Diethylaniline pops up under CAS numbers and names like DEA, C.I. 20100 (when used as a dye base), or even old-fashioned trade monikers from European dye catalogs. Search engines aren’t always reliable here; researchers can miss key safety warnings or cross-reference hazards if they aren’t careful to check every alias a substance carries. This tangle of synonyms makes a strong case for chemical literacy, especially for students and young workers jumping between different supplier documents or technical books.

Staying Safe and Keeping Operations Clean

Amine odors linger in ventilation systems, on gloves, and on a chemist’s memory. Getting too comfortable with chemicals like N,N-Diethylaniline introduces more risks than most would expect. Prolonged exposure irritates skin, eyes, and lungs, and spillage threatens local waterways. I remember days scrubbing down benches and tracking down every spill because careless handling stacked up minor injuries and led to major waste disposal headaches. Every operation—storage, labeling, waste—calls for respect, not just routine. Fume hoods aren’t just a label requirement; they shave off years of avoidable respiratory irritation. Regular refresher trainings on new safety standards help keep everyone sharper, especially with evolving workplace regulations.

Where N,N-Diethylaniline Ends Up

The practical uses of N,N-Diethylaniline reach farther than many realize. Dye and pigment producers lean on this amine because it helps provide subtle color changes and boosts durability in end textiles. Analytical chemists use it as a marker in some instrument calibration protocols, banking on its reactive nature. Some pharmaceutical syntheses adopt the compound as a starting block thanks to its chemical flexibility, though never in final drug formulations themselves. These uses reflect both the creativity and the responsibility required in moving molecules from lab benches into consumer goods or industrial products.

Research Frontiers and Lab Curiosity

Research on N,N-Diethylaniline shifts as the needs of science and industry change. Environmental scientists now probe how residual amines and their byproducts move through soil and water, looking for any sign of accumulation or toxicity in food chains. Synthetic chemists keep poking at novel routes to make the compound cleaner, greener, and in larger volumes with less waste. Work in analytical chemistry aims to devise quicker, cheaper tests for detecting traces in foods, drugs, and wastewater. Old habits—like pouring solvent waste down the drain—face sharper scrutiny, and more people are asking what really happens to a compound once it leaves a facility. Open communication with regulatory bodies and the broader public builds trust and keeps accidents and pollution to a minimum.

Toxicity and What It Means for Human Health

Long gone are the days of handling amines without gloves and splashing waste with abandon. Studies on N,N-Diethylaniline toxicity tie it to possible organ damage with chronic exposure, and animal tests flag warning signs for both workers and local communities. Handling instructions now come with explicit recommendations for gloves, goggles, and proper venting. Environmental monitoring in regions with heavy manufacturing presence catalogs both spills and routine emissions. Workers trained in interpreting toxicity data—for example, knowing the gap between a one-off skin contact and repeated, low-level vapor exposure—navigate their jobs more safely. Discussion about health risks now happens openly in both academic papers and industry protocols, pushing for stronger safeguards every year.

Looking Ahead: Balancing Use with Responsibility

The days of unrestricted chemical growth have passed. Now, scientists and industrial planners both look beyond yields or product tables. Cleaner synthetic methods using renewable feedstocks can bring down waste and cut off pollution at the source. Safer alternatives in dyes and reagents edge out some traditional uses of amines that pose bigger environmental concerns. Regulatory agencies keep pressuring industries to limit emissions and document waste handling step by step. More cross-discipline collaboration brings toxicologists, engineers, and factory operators into the same space, and this kind of teamwork often delivers smarter solutions than lone efforts. Companies and labs that adapt to changing standards and seek transparency with communities gain more than good press—they set themselves up for survival in a world with little patience for chemical shortcuts.




What are the common uses of N,N-Diethylaniline?

What N,N-Diethylaniline Brings to the Table

Anyone who’s spent time looking at the behind-the-scenes world of chemical manufacturing knows there's a surprising cast of unsung heroes. Among the less flashy but deeply useful compounds, N,N-Diethylaniline lands a spot because of its place in research and industry. This clear, oily liquid often smells a bit like an old science lab. It turns up in more places than most folks realize.

Big Role in Textile and Dye Production

Most colorants that end up on shirts, jeans, and specialty fabrics come from a blend of complex chemistry and ingenuity. N,N-Diethylaniline steps in as a starting point for several dyes, like azo dyes and methylene blue. Dye companies rely on this compound because it helps deliver vibrant, lasting color. Without it, your favorite denim shade or printed T-shirt might fade much sooner or never even exist.

Making Pharmaceuticals Work

Pharma labs find in N,N-Diethylaniline a handy reagent to move their drug synthesis along. Not because it ends up in pills themselves, but because it sets up other, more complex reactions. It makes possible the production of antiseptics and local anesthetics. Its chemistry opens the door to some widely used medicines. Keeping those supply chains healthy means knowing your way around compounds just like this one.

Photography’s Quiet Assistant

Traditional film photography may not be front and center these days, but plenty of artists and labs still swear by chemical methods. Old-school photographic developers often feature N,N-Diethylaniline as a key component. It helps transform latent images on film into visible ones. My first darkroom experience came with the sharp scent of these chemicals. The process stuck with me as much as the prints did. Without N,N-Diethylaniline and its ilk, black-and-white film wouldn’t have quite the same magic—or the same sharp contrast.

Pushing Forward in Organic Synthesis

Chemistry researchers don’t let a reliable reagent go unused. N,N-Diethylaniline finds a home in labs worldwide as a starting material for everything from dyes to synthetic flavors. Its chemistry is well-established, making it a dependable choice for complicated reaction pathways. Researchers working on new treatments or advanced materials find themselves leaning on tried-and-true compounds. In my own university days, the name appeared regularly in lab notes, reminding me of the deep history and continuing relevance of certain building blocks.

Safety and Environmental Concerns

Any chemical’s story needs a straight talk about risks. N,N-Diethylaniline can be harmful if mishandled, potentially affecting the nervous system and skin. Improper disposal pollutes water and soils. Workers and researchers depend on gloves, proper ventilation, and training to manage these risks. Companies and regulators keep tight controls over its use. Advances in greener chemistry aim to lessen environmental impact by creating safer substitutes or better containment.

Better Practices and What Comes Next

Experience with N,N-Diethylaniline shows the value of compound-specific training and clear labeling. Working with hazardous materials means not just following rules but understanding why they exist. Industry groups share best practices and push for safer alternatives. Green chemistry continues to hunt for replacements that match N,N-Diethylaniline’s usefulness with less downside. Community watchdog groups keep the pressure on to ensure companies manage waste responsibly and protect local waterways.

N,N-Diethylaniline works behind the curtain in textile, pharma, and artistic fields. Its ongoing story shows the push-pull between industrial progress and safety, between palette and pollution. Keeping that balance takes commitment from everyone who crosses paths with it.

What are the safety precautions when handling N,N-Diethylaniline?

Getting Familiar with the Hazards

N,N-Diethylaniline isn’t a household name, but it’s common enough in labs making dyes, certain drugs, or rubber chemicals. Anyone who’s spent time with aromatic amines has probably read those safety sheets and figured the usual gear would cover it. Still, more folks get caught off guard by simple mistakes—forgetting to close a container, getting a little on the skin, or missing that one whiff of vapor because the fan was off. It can cause skin and eye irritation, triggers headaches or nausea, and long-term exposure messes with blood cells. Once you know the risks, you realize working with this chemical needs more than making sure your hands are clean at the end of the day.

The Basics: Gear That Matters

Not all lab coats or gloves cut it. I’ve seen nitrile gloves hold up better than latex with N,N-Diethylaniline. Splash goggles beat safety glasses since the liquid creeps under if you’re not careful. Thick cotton or flame-resistant lab coats help for spills and small fires. Wearing closed shoes, no open-toed sandals, keeps feet safe if something hits the floor. Taping cuffs, pulling back sleeves, and actually tucking in—these small steps take no extra effort yet make a difference.

Proper Handling—Distraction Turns Small Mistakes Big

Fume hoods aren’t just for looks. Even short mixing or pouring sessions go in the hood because the vapors sting the eyes and nose quick. Leaving a bottle open after measuring may sound minor, but I learned from others' mistakes—vapors spread fast, and that smell lingers long after. Folks avoid food or drinks anywhere near chemical benches, since cross-contamination happens. Labeling feels redundant, but surprise clear liquids without a tag always bring trouble.

Storage: Not a Place for Corner-Cutting

N,N-Diethylaniline lives best in a cool, dry cabinet, away from direct sunlight and oxidizers. I watched cases where chemical cabinets kept leaking or rusty cans perched above head height. Down the line, that means cracked containers and messy accidents. Check that the lid closes snug, and avoid glass if you can; shatterproof plastic bottles save on sweeping up. Never keep more than you need for current projects—old stock goes off, and old labels fade out the warnings.

Accidents—Speed Matters, But So Does Preparation

Spills turn clean benches into hazards instantly. Having a properly stocked spill kit—absorbent pads, gloves, disposable scoops—makes it easier. Trying to dilute or wash away with water only sometimes works; blotting up then neutralizing with the right solution gets better results. Splashes on skin benefit from immediate washing with soap and cool water, no hesitation. Seemingly minor contact can bring rashes or higher absorption than most realize.

Training and Awareness Create a Safer Lab

Most people look at material safety data sheets once, thinking it's just paperwork. The real change comes from ongoing training. Labs holding quick refreshers or sharing what went wrong last week keep everyone sharp. Even experienced folks forget steps under deadline pressure, and new staff often miss risks hiding in plain sight. Culture shapes habits, and creating a space where anyone calls out unsafe steps—without fear of pushback—lowers incidents.

Looking Beyond Compliance

Focusing only on checks and OSHA posters sets a low bar. Those who make time for honest talks, regular gear checks, and simple habit-building cut down exposure for everyone. I've seen labs where these routines stopped accidents before they started, because someone cared enough to speak up or clean up one extra bottle. Keeping your guard up with N,N-Diethylaniline keeps the lab running safer, and people healthier long term.

What is the chemical structure and formula of N,N-Diethylaniline?

Understanding Its Make-Up

N,N-Diethylaniline doesn’t pop up in dinner conversations, but it’s familiar territory for anyone with a background in chemistry or dye manufacturing. It belongs to the family of aromatic amines. This isn’t just some technical phrase—it tells us this molecule starts with a benzene ring, the same six-carbon structure found in many things, from gasoline to aspirin. At its core, you’ll find an aniline group, and what makes this compound stand out is that the nitrogen atom ties itself to not just one, but two ethyl groups instead of plain hydrogens.

Take a look at its chemical formula: C10H15N. In the world of organic chemistry, this means there’s a framework of ten carbon atoms, fifteen hydrogens, and one nitrogen atom all laid out in a specific shape. If you drew its structure, you would sketch a benzene ring (that classic hexagon) bonded to a nitrogen. This nitrogen then connects to two ethyl chains—each one made of two carbons and five hydrogens (–CH2CH3). It’s a simple shift—replacing the usual hydrogens on aniline’s nitrogen with more complex ethyl parts—but that small detail changes a lot about how this molecule behaves.

Context in Real Life

I remember using N,N-Diethylaniline while tinkering in a research lab. It’s an oily liquid, almost colorless but with a faint amine-like smell. Lab safety was always the rule, and for good reason—this compound can irritate your eyes and skin, so gloves stay on. What sticks with me is how chemists, especially those who synthesize dyes or pharmaceutical intermediates, depend on these modest tweaks to basic molecules. They often need just enough difference to tune color or potency.

Why Structure Matters

Benzene rings build the backbone for heaps of useful products—solvents, dyes, pharmaceuticals. Here, the ethyl groups stabilized the molecule in oily solutions and improved its ability to mix with organic solvents. Its layered structure gives it unique properties. N,N-Diethylaniline readily dissolves in organic solvents but shuns water. Its structure opens the door to making azo dyes—brilliant reds and yellows that show up in everything from synthetic fabrics to printer ink.

Evidence points to its role as an intermediate in producing triarylmethane dyes and even as a component in some pesticides. The real story is about those ethyl chains. They push electron density towards the nitrogen, which then shares this with the benzene ring, boosting reactivity when forming bonds or swapping atoms in further chemical synthesis.

Concerns and Safer Handling

Organic chemists face challenges with aromatic amines that extend beyond staining hands or glassware. The toxic potential of these substances has spurred tighter occupational rules worldwide. Watchdogs like the European Chemicals Agency have flagged aromatic amines due to their risk in high exposures. While you might not encounter N,N-Diethylaniline at home, factories working with it must keep air clean and workers protected. The right solution is not to ban chemicals outright, but to respect them: use engineering controls, PPE, closed systems, and smart labeling. Trained eyes spot risks before they become problems.

Moving Chemistry Forward

Chemists continue tweaking classic building blocks like N,N-Diethylaniline, chasing safer and more efficient ways to craft molecules. Alternatives to toxic solvents and greener synthetic routes are getting traction. Progress comes from clear understanding: knowing what atoms you’re working with, how they shape each other, and keeping a respect for both the potential and the hazards in every bottle hidden behind the storeroom door.

How should N,N-Diethylaniline be stored?

Understanding the Risks and Why Storage Matters

You walk into any chemical storage room and spot a bottle labeled N,N-Diethylaniline, and that moment really brings home the importance of proper storage. This chemical isn’t some kitchen cleaner—handling it with respect means more than following the directions on a label. This liquid brings both health concerns and fire risks. From experience working in labs, I’ve seen the headaches caused by poor planning. All it takes is one spill or a leaky bottle to turn a normal day upside down. N,N-Diethylaniline, used in dyes and pharmaceuticals, can irritate skin, eyes, and lungs. Left uncapped or stored with the wrong materials, it becomes a ticking hazard.

Keep It Cool, Keep It Dry, Keep It Away from Ignition

Temperature plays a big role in safety. Exposure to heat or direct sunlight nudges this liquid toward instability. Chemists keep it out of the heat, putting bottles in a cool, well-ventilated cabinet. Anything above room temperature raises evaporation and the buildup of flammable vapor. An old lab trick is to stash sensitive chemicals low to the ground, away from skylights or heaters, not just on the nearest shelf.

Humidity causes trouble too. Water can seep in and react with a poorly closed container, especially if a cap isn’t tightly fastened. So cabinets should stay dry. Desiccators or sealed secondary containers go a long way in preventing accidents. Some lab caretakers add silica packs—an easy way to cut moisture and save money on ruined materials.

Flammable liquids like N,N-Diethylaniline need space away from spark sources and incompatible substances. That means not shoving it next to oxidizers, acids, or anything that gives off strong fumes. A separate flammables cabinet, made of metal, with a grounded latch, works best. Even in small quantities, storing it right makes a difference. Insurance companies and regulatory checks often look for proof that chemicals are locked and labeled, and that guidelines like OSHA and NFPA have been followed. Failure here can lead to real-world injuries, lost licenses, and fines that no company wants.

Labeling, Segregation, and Vigilance: Building Safer Habits

Trust gets built on habits—always labeling containers, never mixing leftovers, and marking down expiry dates. In my own practice, I mark every container with the purchase date and never rely only on its original label. Some colleagues create checklists to track condition, cap tightness, and levels every month.

Segregation makes a difference. This chemical belongs with other flammables in a labeled section, away from acids and bases. Shared lab spaces only work if each user respects the system. Checklists, inventory logs, even plain communication save time and lives. I remember stories of labs that ignored these steps, resulting in cross-contamination and hospital visits. Preventable, but only if someone takes responsibility from the start.

Disposal matters too. No pouring leftovers down the sink. Closed, clearly marked waste containers await pickup by licensed handlers. Years ago, I watched a new tech toss a small bottle in the regular bin—everyone spent hours documenting and reporting that mistake. Regular retraining and reminders keep standards high.

Training: The Most Valuable Safety Tool

No storage solution replaces hands-on training. Safe habits get taught by senior staff, not just read in manuals. Whether it’s a high school lab or a multinational plant, routine drills and ongoing education do more to prevent accidents than fancy cabinets alone. It’s people, not policies, that ensure these risky substances never become tomorrow’s headline.

What is the purity specification for N,N-Diethylaniline in commercial products?

Why Purity Matters in Chemical Sourcing

Every chemist working in industry knows that a reagent’s purity can make or break product quality, downstream reactions, or safety profiles. N,N-Diethylaniline, a common intermediate in dyes, pharmaceuticals, and pesticides, isn’t an exception. For anybody handling the technical details in a chemical plant or lab, checking the guarantee for purity isn’t just a box-ticking exercise. There’s a huge difference between industrial grade and laboratory grade, and for this chemical, the label isn’t just a marketing slogan.

Typical Purity Specified by Manufacturers

N,N-Diethylaniline in commercial markets usually comes with a purity specification of at least 98%. Reputable suppliers lay out the certificate of analysis showing that the chemical meets this number by gas chromatography or similar analytical methods. The remaining 2% often includes substances like water, monoethyl aniline, diethyl ether, or other related amines. It’s easy to overlook the 2%, but small amounts of impurities can cause problems if they react or show up as unknowns in sensitive processes. For research labs creating advanced catalysts, even 98% isn’t always enough.

Common Impurity Concerns and Supply Chain Issues

I noticed in my own experience sourcing intermediates for dye manufacturing just how tricky it can be to keep impurity levels under control. If a shipment showed up lean on purity, the final color yield in our batches dropped, and sometimes, equipment required extra cleaning to flush out residues. Some colleagues in pharmaceuticals have dealt with headaches from residual aniline traces, which need monitoring due to health and regulatory concerns.

Consistency matters as much as the actual number on the label. Large-scale plants are sensitive to lot-to-lot variation. A poorly controlled batch can stall an entire line, causing financial losses way beyond the cost of the raw chemical itself. Especially with tightening standards from customers in Europe, North America, and Japan, trace-level reporting of heavy metals, chloride content, and other volatile impurities has become standard practice.

Tracking, Testing, and Quality Control

Smart buyers ask for more than just a purity number; they want to know the whole impurity profile. Labs run checks like IR, NMR, and even mass-spectrometry to look for low-level contaminants. Documentation tracing back to the manufacturing process provides a safeguard—a paper trail showing that process water, solvents, and by-products stay within control throughout the batch. Suppliers who skip that level of quality tend to lose serious buyers fast. In my own work, I always review the latest analysis before accepting any delivery to our plant. Accepting "sample" shipments without such checks led to a lot of trouble once, costing us more in cleaning and downtime than any price saving.

Improving Quality and Building Trust

There’s room for improvement in the industry. Some suppliers step up with tighter batch analytics, automatic in-line sensors, or regular third-party verification, but standardizing those practices would raise the bar across the board. Customers can help by being clear on requirements, demanding full impurity disclosure, and being willing to pay a fair price for extra purification or improved traceability. Regulators play a part by pushing for clearer guidelines, especially for customers using amines in food or medicine.

Above all, knowing exactly what’s in each drum or bottle means fewer surprises, smoother processes, and safer products. For anyone in this business, that’s worth paying close attention to every single time.

N,N-Diethylaniline
N,N-Diethylaniline
N,N-Diethylaniline
Names
Preferred IUPAC name N,N-Diethylaniline
Other names Diethylaniline
N,N-Diethylbenzenamine
N,N-Diethylphenylamine
N-Phenyl-diethylamine
DEA
Pronunciation /ˌɛnˌɛn.daɪˌɛθ.ɪl.ˈæn.ɪˌliːn/
Identifiers
CAS Number 91-66-7
Beilstein Reference 605673
ChEBI CHEBI:35725
ChEMBL CHEMBL14036
ChemSpider 7275
DrugBank DB02049
ECHA InfoCard 100.057.831
EC Number 204-493-5
Gmelin Reference 8285
KEGG C02349
MeSH D003972
PubChem CID 7009
RTECS number JE5600000
UNII 4AK09F06A2
UN number UN2713
Properties
Chemical formula C10H15N
Molar mass 149.24 g/mol
Appearance Colorless to pale yellow liquid
Odor amine-like
Density 0.936 g/mL at 25 °C (lit.)
Solubility in water slightly soluble
log P 2.85
Vapor pressure 0.133 hPa (20 °C)
Acidity (pKa) 5.89
Basicity (pKb) 6.58
Magnetic susceptibility (χ) -46.6·10⁻⁶ cm³/mol
Refractive index (nD) 1.553
Viscosity 2.35 cP (25°C)
Dipole moment 2.22 D
Thermochemistry
Std molar entropy (S⦵298) 229.6 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) 71.5 kJ/mol
Std enthalpy of combustion (ΔcH⦵298) -4345.8 kJ/mol
Hazards
GHS labelling GHS02, GHS07, GHS08
Pictograms GHS02,GHS07,GHS08
Signal word Warning
Hazard statements H302, H312, H315, H319, H332, H351, H373
Precautionary statements P261, P264, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P330, P337+P313, P403+P233, P501
Flash point 87 °C
Autoignition temperature 440 °C
Explosive limits Explosive limits: 0.7–6.4%
Lethal dose or concentration LD50 (oral, rat): 850 mg/kg
LD50 (median dose) LD50 (median dose): 891 mg/kg (oral, rat)
NIOSH KN0355000
PEL (Permissible) PEL (Permissible Exposure Limit) of N,N-Diethylaniline is "5 ppm (25 mg/m3)".
REL (Recommended) 50 mg/L
IDLH (Immediate danger) 50 ppm
Related compounds
Related compounds Aniline
N-Methylaniline
N-Ethylaniline
N,N-Dimethylaniline
N,N-Diethylaniline sulfate