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Looking at 4-Aminothiophenol: More Than a Simple Chemical

Historical Development

Think back to the early chapters of organic chemistry. In labs filled with glassware and passionate arguments over mechanisms, chemists stumbled upon the amine and thiol functional groups—useful, but sometimes tricky to control. 4-Aminothiophenol came along as a sort of bridge between those two worlds. Its story runs through experiments and papers scattered over the last century. Researchers hunting for functionalized aromatics with both sulfur and nitrogen found this compound brings good reactivity without the baggage of instability some thiols drag along. In my time studying aromatic substitution, 4-Aminothiophenol always had a seat at the table when folks needed both a nucleophile and a handle to hang further groups on. It didn’t come in a blaze of glory, but as scientists dug into dye chemistry, pharmaceuticals, and the world of sensors, this molecule kept showing up—an old friend in a new context, making things possible that plain anilines or benzenethiols couldn’t handle alone.

Product Overview

If chemistry had unsung heroes, 4-Aminothiophenol would get a lifetime achievement award. Its structure—an aromatic ring with an amino group and a thiol on opposite sides—lets it play a balancing act: enough solubility for workup, enough reactivity to grab onto metal surfaces and build new molecules on the fly. In the stacks of bottles that crowd every research shelf, this one never collects much dust. You’ll find it in the raw materials shipments to electronics labs and in the toolkits of surface scientists looking to tweak nanoworlds. A bottle labeled “4-ATP” seems humble, but chemists who know what’s inside see a dozen experiments waiting to be set up.

Physical & Chemical Properties

Chemicals don’t have personalities, but if they did, this one would smell…unpleasant. The thiol group makes its presence known as soon as you crack the cap. The pale yellow powder clumps in humid air—water seeps in through any gap, showing the molecule’s willingness to form hydrogen bonds despite the rugged aromatic core. Chemists use its moderate melting point and unique UV absorption features to check purity. The amino group soaks up protons in acidic media, and the thiol forms strong bonds with gold, silver, or even certain polymer matrices. These properties aren’t just textbook trivia—for me, they’ve meant easy attachment to electrodes or rapid participation in nucleophilic substitutions, tasks that many other reagents fumble.

Technical Specifications & Labeling

Forget the sterile numbers for a moment and focus on how scientists approach this chemical. Purity checks matter. Minor impurity, maybe some oxidation to disulfide, and sensitive experiments start to wobble. Reliable labeling means more than just a barcode; it’s shorthand for years of collective headaches averted by those who understand what even a trace of the wrong compound can do. Companies that ship 4-Aminothiophenol with less-than-clear information on impurity levels or lot consistency throw a wrench into any decent research workflow. As a chemist, I look for tech sheets that detail synthesis origin, storage advice, and how to spot degradation.

Preparation Method

Classic syntheses teach patience. Most routes start with p-nitrothiophenol, then work through reduction—old-school chemists used iron filings and hydrochloric acid, while modern labs might reach for catalytic hydrogenation. The process carries hazards, not just from flammable hydrogen but also from the ever-present sulfur odor and the touchiness of some intermediates. Succeed, and you’ve got a product that lines up reliably with NMR and IR; cut corners, and by-products clog every chromatography column. I still recall the frustration of trying to purify a batch from a shortcut synthesis—there’s a reason established protocols are passed down from lab to lab.

Chemical Reactions & Modifications

Run 4-Aminothiophenol through condensation reactions—it grabs electrophiles with the amino group. The thiol, on the other hand, makes strong connections with gold surfaces, so if you’re building a self-assembled monolayer on a chip, this is your starting point. The compound’s unique setup means you can tailor further modifications—acylation, alkylation, or coupling with diazonium salts—using either side. In surface science, the thiol attaches to a substrate, freeing the amine for sensing chemistry or post-functionalization, a strategy used everywhere from biosensors to organic photovoltaics. Reaction conditions matter, though; oxidation ruins the thiol, so careful exclusion of air becomes a habit in every protocol.

Synonyms & Product Names

Names sometimes hide similarities or connections. Most researchers know 4-Aminothiophenol just as “4-ATP”, but suppliers and older literature might call it “para-aminobenzenethiol”, “p-aminothiophenol”, or “4-mercaptoaniline”. These aliases can trip up the uninitiated. Anyone digging through catalogs trying to compare prices or specs needs to keep an eye out for interchangeable product codes and spellings. Over years of catalog diving, missing out on a cheaper or purer source just because the chemical’s synonym isn’t recognized hurts more than it should.

Safety & Operational Standards

Experience shapes habits, especially with noxious chemicals. A mashup of aniline and thiol means gloves are not optional and open windows become a must. The smell lingers, hinting at the molecule’s volatility and potential for skin and respiratory irritation. Regulatory bodies set exposure limits based on real toxicology, not just prudence. Equipment for handling comes with clear instructions: use in a fume hood, minimize spills, dispose in the right waste stream. Mistakes with this compound often teach unforgettable lessons, sometimes to the whole lab. Safety data sheets for 4-Aminothiophenol spell out dangers with more authority than classroom theory; years of working with these sheets teach respect that pure academic knowledge can’t offer.

Application Area

Fields most folks never hear about rely on 4-Aminothiophenol, whether they admit it or not. The compound’s gold-thiol affinity built a legacy in biosensor research—antibodies and oligonucleotides anchored to surfaces by this tiny bridge. Electronic devices owe parts of their sensitivity to the way self-assembled monolayers (SAMs) passivate or functionalize surfaces. Analytical chemists rely on it for Raman spectroscopy enhancements—attach it to a metal nanoparticle, and suddenly weak signals become readable. Drug designers tweak its structure to build intermediates for more complex molecules. Looking across patents, papers, and industrial protocols, 4-Aminothiophenol stands out as a tool that enables new discoveries but rarely grabs headlines.

Research & Development

Every R&D cycle chases improved performance—faster sensors, more stable coatings, better detection limits. 4-Aminothiophenol hardly seems glamorous, but test after test show it offers results reproducibility and straightforward chemistry. Newer research explores fine-tuning how molecules attach to surfaces, controlling the density or orientation of SAMs. Scientists explore whether additional features—fluorescent tags, polymerizable groups—added to the base molecule can improve device performance. In my own experience, the compound’s staying power comes less from novel properties and more from consistency; it provides a known starting point for building increasingly complex assemblies, and new students still benefit from hands-on work with it in area after area.

Toxicity Research

Aromatics with sulfur or amine groups always raise flags in toxicology. Decades of animal studies point toward moderate acute toxicity, skin sensitization, and potential long-term effects from chronic exposure. Regulators set storage and handling protocols based on studies that tracked inhalation risks, skin absorption, and environmental persistence. Disposal practices grew out of this evidence—labs must neutralize waste and avoid sending untreated material down the drain. For chemists, the solution never comes by ignoring warnings. Good ventilation, careful weighing, proper glove selection, and solid training are not just checkboxes; they protect bodies and careers. Over the years, I’ve seen the consequences of short cuts—improper handling lays bare just how real the risks in even small-scale work can be.

Future Prospects

A chemical like 4-Aminothiophenol doesn’t just fade away when fancier molecules emerge. Its structure and utility keep it in demand in surface chemistry, device fabrication, and diagnostic development. The rise of renewable energy and better medical sensors highlights the continuing need for molecules that anchor functional layers to metals and semiconductors in a reliable way. Researchers now look hard at greener synthesis methods, lower-toxicity alternatives, and automated modification techniques—areas where the lessons learned from years of working with 4-Aminothiophenol feed directly into better options for the next generation. Even as nanotechnology and bioconjugation become the buzzwords of funding grants, this compound’s adaptability gives it a long tail; new applications spring up wherever strong surface anchoring and dual-reactive groups are handy. Based on the weight of published results and ongoing demand, it’s clear that, for now, 4-Aminothiophenol’s story continues in the hands of every chemist who values reliability, versatility, and the chance to turn small molecules into big solutions.




What is 4-Aminothiophenol used for?

What Is 4-Aminothiophenol?

4-Aminothiophenol pops up in labs across the world. With both an amino group and a thiol group locked onto a single benzene ring, it brings two reactive features chemists like to harness. Those functional groups aren't just scientific jargon—they lend this molecule its character. The amino group reads basic and reactive, and that sulfur-hydrogen tail gives the compound a strong odor and a knack for grabbing onto metals.

Turning Surfaces into Sensors

My first encounter with 4-aminothiophenol came in grad school. A friend working on biosensors needed to anchor antibodies onto gold. She reached for 4-aminothiophenol without hesitation. That thiol group latches tight to gold surfaces. Sleek as it sounds, creating a self-assembled monolayer is almost like magic in a beaker. The molecule arranges itself into a tidy layer, ready for further tinkering.

Once you have a monolayer, you gain a reactive surface. The amine sticks up, free to react with something else—enzymes, biomolecules, fluorescent tags, you name it. That’s how research groups transform bare gold into devices that light up in the presence of toxins, allergens, or even viruses. The sensitivity and selectivity of modern diagnostic platforms owe a lot to this sort of surface chemistry. There are reports showing that 4-aminothiophenol-based monolayers can detect substances at nanomolar concentrations. Those results aren't just nice-to-haves; they change how fast hospitals can get answers.

Molecular Wires and Electronics

The world doesn’t just need gold-plated surfaces for biology. Electronics research depends on nanoscale building blocks, and 4-aminothiophenol steps up again. Organic semiconductors and molecular electronics need reliable connectors. Here, scientists layer the molecule between electrodes, making molecular junctions that can act as switches. The amine and thiol groups make it easier to anchor with precision.

Published studies from the past five years show these molecular wires hold promise for tiny transistors and memory devices. Research groups have built single-molecule electrical switches using 4-aminothiophenol, pushing data storage far past what silicon alone could handle. Real-life use still faces hurdles, chiefly cost and stability, but steady progress points to new possibilities in flexible electronics or even smart packaging.

Environmental and Safety Factors

It’s easy to marvel at the science, but use at scale brings safety questions. 4-Aminothiophenol carries a strong smell and can irritate eyes, skin, or lungs. Labs employ proper protective equipment and fume hoods. Disposal matters, too—thiols don’t just break down harmlessly, and regulators keep an eye on their release. These aren’t just bureaucratic hurdles, either. Safe handling earns trust from lab workers and neighbors. Responsible scientists focus on limiting exposure and finding alternatives wherever practical.

What Comes Next?

Innovation keeps marching. Chemists keep searching for molecules that do more with less toxicity. Bio-inspired and biodegradable alternatives get a lot of attention, but few match the ease and reliability 4-aminothiophenol offers. For now, it remains part of the toolkit for those working at the busy intersection of chemistry, engineering, and medicine. The next leap in diagnostics, computing, or sustainable technology might just still depend on this unassuming but powerful little molecule.

What is the molecular formula and structure of 4-Aminothiophenol?

What is 4-Aminothiophenol?

4-Aminothiophenol belongs to a class of organic compounds known for bringing both a thiol group and an amine group to a benzene ring. Think of it as a molecule with two tails, each one bringing a different set of reactions and uses. It’s commonly shortened to "p-aminothiophenol" due to its para-substituted structure.

Molecular Formula and Structure

This molecule has a clear and simple formula: C6H7NS. That comes from a benzene ring (C6H4) with an amino group (-NH2) and a thiol group (-SH) attached at opposite sides.

The arrangement really matters at this scale. On a benzene ring, the positions are crucial. For 4-aminothiophenol, the amino group chains off carbon #1. The thiol group plants itself on carbon #4. Chemists call it a "para" arrangement.

To picture it, draw a six-sided benzene ring. Place the NH2 directly above a carbon, then tuck the SH group straight across. It’s clean, symmetric, and makes the molecule straightforward to identify on a lab bench or a whiteboard.

Why This Arrangement Matters

Anyone who’s handled 4-aminothiophenol in the lab knows its uses come from this simple arrangement. The -SH group (thiol) has a strong affinity for metals. That opens doors for creating self-assembled monolayers, the thin, single-molecule coatings used all over nanotechnology and electronics. Gold bonds tightly with sulfur, so a gold surface dipped in a solution of 4-aminothiophenol gets a tight layer of these molecules, with their amino groups poking upward.

The NH2 group (amine) reaches out toward the environment, ready to hook up with acids, other functional groups, or assist in further reactions. This two-sided nature turns 4-aminothiophenol into a bit of a Swiss Army knife for chemists. Applications spill into biosensors, where its structure helps immobilize enzymes or antibodies onto metal surfaces for rapid detection of biological signals.

Challenges and Safety

Anyone thinking of scaling up the use of 4-aminothiophenol meets a set of safety hurdles. Thiol compounds often smell sharp, like rotten eggs, and are toxic in large quantities. Proper ventilation and careful handling matter in the lab or factory.

It’s not just about keeping humans safe. Thiols, if not managed well, leach into water or soil. That creates an environmental headache. Companies in charge of producing or using 4-aminothiophenol must install trapping and neutralization systems—activated carbon filters, chemical scrubbers, or waste management processes—before releasing anything into the environment.

Looking Forward: Solutions and Improvements

Safer synthesis routes need to replace older methods involving excess harmful reagents. Researchers dig into greener chemistry—solvents derived from plants, lower energy reactions, efficient recycling of residues. Training technicians and chemists on best safety practices keeps both workplaces and the surrounding environment healthier.

The benefits from using 4-aminothiophenol are significant in fields like electronics, biosensing, and surface science. Keeping human and environmental health at the forefront ensures continued access to its unique properties, all without repeating mistakes that damaged trust in the chemical industry in the past.

How should 4-Aminothiophenol be stored and handled safely?

Recognizing Real Risks in the Lab

Over the years, I’ve seen what can happen when folks let their guard down around chemicals, especially substances like 4-Aminothiophenol. A lot of folks gloss over the real risks because it’s not as flashy or as famous as some other compounds. The facts tell a different story. Even a small spill can send sharp fumes through a workspace, and folks who touch it with bare hands can end up with skin and eye irritation. I’ll be honest, I once saw a coworker get a painful rash because he skipped the right gloves. People don’t always learn the easy way.

The Right Way to Store It

Small bottles of 4-Aminothiophenol show up in research labs and chemical storerooms. This compound, with its distinct sulfur scent, demands respect. If you just toss a bottle in a cabinet, you’re setting up trouble. The stuff reacts fast with acids and oxidizers. You want to keep it locked up in a cool, dry spot, away from anything with acid fumes. Humidity can kick it off too, so a tight seal is non-negotiable. I always write clear labels and double-check that nothing nearby could start a reaction if the bottle broke. Every chemist I trust does the same.

Don’t Skimp on Protection

This is not the time for shortcuts. I pull on nitrile gloves, not latex ones, because thiol groups chew through poor-quality barriers. I wore latex once—never again. You want a lab coat without holes, splash-proof goggles, and a fume hood running. Even a bit left open on a benchtop can mess up the air. I remember a time ventilation broke down in a partner lab, and three people had to step out for air in a hurry because someone was working open-bottle. No paperwork matters more than your lungs and your eyes.

Spills: Don’t Wait to Clean Up

Every lab I’ve worked in kept a chemical spill kit within reach. The key: move quick and don’t freelance your response. Absorb the liquid with inert material—sand or vermiculite works—then scoop it into a sealed waste container. Waste disposal rules matter, both for keeping people safe and avoiding fines. Pouring it down the drain isn’t just lazy; it’s dangerous for the bigger environment. The weight of responsibility never goes down, no matter how many times you run through the drill.

Sharing Knowledge Keeps Us Safer

Anyone who works with chemicals long enough ends up with stories about close calls. Good training cuts those close calls in half. The toughest thing is making sure newcomers don’t pick up bad habits. I like to see folks walk through storage and safety steps with a veteran before turning them loose. No amount of automated reminders replaces a smart supervisor. Swapping safety tips over coffee has saved more skin than lectures alone ever could.

Stronger Habits, Fewer Accidents

The safest labs set rules and check up on them, but they don’t stop at box-ticking. They make careful storage and full protection non-negotiable. People learn from others’ mistakes so they don’t make them again. Having the right gear and clean habits never gets old. People remember to respect chemicals like 4-Aminothiophenol when everyone’s watching out for one another. That’s how more folks go home healthy, every day.

What are the potential health hazards and first aid measures for 4-Aminothiophenol?

Why Knowing Risks Makes a Difference

4-Aminothiophenol shows up in research labs, electronics work, and certain industrial processes. The name sounds harmless, but the reality demands caution. This chemical contains both an amine and a thiol group—two tricky functional groups from a health perspective. People who deal with it often trust their training, but memory slips or basic complacency put health on the line.

Major Health Hazards

Based on my lab days, even short encounters with organic thiols like this one tell you the risks pretty quick—the odor alone is aggressive and signals potential toxicity. 4-Aminothiophenol can irritate skin, eyes, the lining of the nose, and throat. If you get any of it on your skin, redness, itching, or rashes may develop. Eye contact feels unpleasant almost instantly, and—worse—can injure corneas if the exposure is serious.

Inhaling its fine dust or vapors often brings on coughing, shortness of breath, and sometimes wheezing. Prolonged exposure influences more than comfort; it may cause headaches, dizziness, or even nausea. Taking this further, animal toxicity data suggest long-term contact could damage organs over time, especially the liver and kidneys, since thiols stick around in tissues once absorbed. No comfort for those who realize too late how their PPE failed.

Swallowing 4-aminothiophenol poses greater trouble. Stomach pain, vomiting, and central nervous system symptoms (confusion, weakness) may follow ingestion. With chemicals in this class, there's always worry about lasting harm—so nobody should treat ingestion cases lightly.

Wisdom from Experience: Quick, Targeted First Aid

I learned early on nobody expects an accident—especially in a lab coat. Any sign of contact means acting fast, not waiting to “see what happens.” Start with removing contaminated clothing right away to limit further spread. Flush skin under running water—15 minutes is the old-school rule because it buys time for the chemical to wash off before it soaks in.

If someone catches fumes, fresh air always comes first. Guide the person outside or near an open window if possible. For serious breathing trouble, an oxygen mask helps, but those usually sit in designated safety kits (a reality only in larger facilities). If someone swallows even a trace, don’t reach for that glass of water or induce vomiting—call poison control and watch for symptoms while help is on the way.

With eyes, don’t skip steps: eyelids open, water flowing, and a good 15-minute rinse. Even a little pain means the body is signaling something wrong. Seek medical attention, whether it seems mild or serious.

Building Safer Handling Habits

From years in shared workspaces, safety rests in routines. PPE—gloves like nitrile and splash goggles—should sit near the workbench, not on a shelf across the room. Respiratory protection isn’t just for show; people forget how quickly organic vapors reach dangerous levels in small spaces. Most chemical accidents happen in predictable situations: hurrying, talking, forgetting to review a safety sheet. Print the SDS and stick it on the wall.

Labs and factory floors get safer when every worker stays familiar with emergency showers and eyewash stations. I’ve seen lives changed by the extra half-minute it took to find the right place. Practice is cheap insurance.

Pushing for Better Solutions

Technology can do more. Automatic fume hoods, chemical detectors, and zero-tolerance storage policies help lower accident rates. Substitution—choosing a chemical that gets the job done with less hazard—sometimes gets overlooked. And more voices at the table: workers, not just managers, should help define safety policy. Real safety culture sticks when it’s built from shared stories and clear accountability.

Where can I buy 4-Aminothiophenol and what is its purity or grade?

It’s Not Just About Finding a Bottle

Searching for 4-aminothiophenol kicks up a different sort of challenge compared to tracking down something basic like sodium chloride. This chemical—an aromatic amine—tends to attract more questions than answers from newcomers. Whether you’re in an academic lab, a materials science group, or a startup’s R&D bench, the journey starts with sourcing and purity.

Where Scientists and Engineers Shop

Several specialty chemical suppliers carry 4-aminothiophenol. Sigma-Aldrich (now under MilliporeSigma in the US), TCI (Tokyo Chemical Industry), Alfa Aesar, and Thermo Fisher Scientific usually show up first in online searches. These companies have grown their reputations over decades, keeping up with shifting regulatory frameworks and stricter safety demands. Ordering from them usually gives peace of mind, at least about what’s in the bottle matching the label.

Why Purity Can Make or Break a Project

Purity sits at the center of any decision on buying chemicals. My own years in research labs taught me that even small traces of contaminants—iron, sulfur, or traces of other amines—can wreck an experiment or twist results until they’re meaningless. Most suppliers offer 4-aminothiophenol in purities of 97%, 98%, or even 99%, sold under grades like “analytical,” “reagent grade,” or “ACS grade.” For surface science or sensor fabrication, many teams won’t settle for anything below 99% because gold-thiol interactions pick up on any contaminant left behind. It’s better to spend on higher-grade material than to repeat months of work.

Pitfalls of Chasing Rock-Bottom Prices

Online marketplaces—Alibaba, Made-in-China, eBay—often promise steep discounts. In my experience, those rock-bottom prices come tied to a knot of risks. You could get a label that claims 99% purity, but the bottle might hold something altogether different. Without a certificate of analysis, it’s a gamble. Buying through the big, well-known suppliers means the paperwork shows up with the shipment, and there’s a real human to call if something goes sideways.

Why Regulatory Compliance Matters

It’s tempting to skip a little bureaucracy in the name of savings, but chemical handling regulations mean more than just red tape. By sticking with reputable suppliers, you’re following legal routes and getting properly labeled material. Some chemicals attract government scrutiny under anti-terrorism or environmental laws, and waste generated from 4-aminothiophenol experiments needs legal disposal. I’ve seen small labs run into audit problems just because they couldn’t show procurement documentation. That sort of trouble doesn’t just slow research; it can halt it for months.

Lessons From Missteps and Fixes That Work

Mistakes in chemical sourcing aren’t rare. I once watched a project burn weeks testing a suspicious batch of 4-aminothiophenol, only to discover a cheaper supplier snuck in spikes of diphenylamine as filler. Lessons like that stick. Now I always start with a supplier with a known track record, and screen the COA before a single milligram goes near a reaction flask.

The Bottom Line

Reliable 4-aminothiophenol comes from established chemical suppliers. Going with recognized names means paying for consistent purity and certified documentation. For those on a budget, price temptation can lead to more headaches than solutions. A little homework reading reviews, checking for regulatory compliance, and, whenever possible, directly contacting sales reps, usually pays off. No experiment, no quality assurance program, can patch up a shortcut at the sourcing stage.

4-Aminothiophenol
Names
Preferred IUPAC name 4-Aminobenzenethiol
Other names 4-Mercaptoaniline
p-Aminothiophenol
PATP
p-Mercaptoaniline
4-ATP
Pronunciation /ˈfɔːr əˌmiːnoʊ θaɪˈɒfɪnɒl/
Identifiers
CAS Number 4-aminothiophenol" CAS Number is "1193-02-8
3D model (JSmol) `$JSmol_Model_chemical/C6H7NS`
Beilstein Reference 1209226
ChEBI CHEBI:17523
ChEMBL CHEMBL16218
ChemSpider 12060
DrugBank DB14106
ECHA InfoCard 100.006.591
EC Number 226-500-0
Gmelin Reference 8146
KEGG C01723
MeSH D000769
PubChem CID 7137
RTECS number XM8575000
UNII 5085Y1DS19
UN number UN3335
Properties
Chemical formula C6H7NS
Molar mass 125.19 g/mol
Appearance Pale yellow solid
Odor unpleasant
Density 1.18 g/cm³
Solubility in water slightly soluble
log P 1.98
Vapor pressure 0.000056 mmHg (25°C)
Acidity (pKa) 3.80
Basicity (pKb) 2.70
Magnetic susceptibility (χ) -39.5 × 10⁻⁶ cm³/mol
Refractive index (nD) 1.677
Viscosity 0.929 cP (20°C)
Dipole moment 3.25 D
Thermochemistry
Std molar entropy (S⦵298) 108.6 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) -26.9 kJ/mol
Std enthalpy of combustion (ΔcH⦵298) -405.3 kJ·mol⁻¹
Hazards
Main hazards Harmful if swallowed, causes skin and eye irritation, may cause allergic skin reaction, harmful if inhaled.
GHS labelling GHS02, GHS05, GHS06
Pictograms GHS05,GHS07
Signal word Warning
Hazard statements Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Toxic to aquatic life with long lasting effects.
Precautionary statements Precautionary statements: P261, P273, P280, P305+P351+P338, P310, P501
NFPA 704 (fire diamond) 3-2-2-W
Flash point 143 °C
Autoignition temperature 385 °C
Lethal dose or concentration LD50 oral rat 230 mg/kg
LD50 (median dose) LD50 (median dose): Oral, rat: 820 mg/kg
NIOSH BZ8575000
PEL (Permissible) Not established
REL (Recommended) 25°C
IDLH (Immediate danger) Not established
Related compounds
Related compounds Aniline
4-Nitrothiophenol
4-Methylthiophenol
4-Chloroaniline
Thiophenol