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4-Chlorophenol: Impact, Risks, and the Road Ahead

Historical Development

Decades ago, the chemical sector underwent massive change as industries reached for efficiency and new compounds. 4-Chlorophenol wasn’t made for the masses but as a sharp tool for manufacturing, pest control, and laboratories. Synthesizing these halogenated phenols first raised eyebrows in the early 20th century, right around the boom of organochlorine chemistry. Back then, little thought went into exposure and environmental drift. What hooked researchers was the compound’s ability to slot into pharmaceutical, agricultural, and dye work, giving it a central role in countless chemical reactions and downstream products. Among many phenols lining the industrial shelf, 4-chlorophenol often stood out for its reliability at the workbench and its knack for chemical transformation, a fact that quickly drove large-scale production.

Product Overview

People working in labs or industrial plants recognize 4-chlorophenol by its sharp odor, solid structure, and unmistakable, biting chemical character. The compound works as an intermediate for making antioxidants, dyes, antiseptics, and pesticides. Its shelf profile is pretty imposing: white crystalline form, with a reputation for reliability in synthesis chains. Over time, the product became critical in wood preservation, rubber processing, and pharmaceutical work. What doesn’t get mentioned enough is that this chemical sits at an uneasy junction—essential in industry, but with a risky reputation lurking in the background thanks to its toxicity and persistence.

Physical & Chemical Properties

4-Chlorophenol defines itself by a simple formula: one chlorine atom stuck onto the fourth carbon of a phenol ring. It melts just above room temperature, runs freely as a colorless or pale-white crystal, and carries a sharp medicinal odor. A pKa of about 9.4 speaks to moderate acidity, typical of phenols. Its solubility serves both as asset and liability: dissolves in many organic solvents, mixes less freely in water, yet the trace that escapes isn’t quick to break down. That resilience, chemically speaking, spells trouble for water treatment and soil clean-up. It can sublimate if left exposed and, like other chlorinated compounds, resists most biological breakdown, which is part of the cleanup headache.

Technical Specifications & Labeling

Labels on drums in my memory always sounded dire: strong warnings about skin contact, eye safety, and ventilation. Everybody in the warehouse knew those hazard symbols meant business. Chemically, suppliers insist on high purity—over 99% for most analytical uses. Impurities like 2-chlorophenol or di-chloro derivatives sent most batches back to the beginning. Packaging used heavy-duty containers resistant to leaks. The chemical’s volatility demanded every shipment pass quality inspection: melting point, water content, GC-MS purity, and a handful of trace impurity tests. There was no hedging or wishful thinking about safety in labeling; users had to know exactly what they were handling.

Preparation Method

If synthesis ever felt elegant, the chlorination of phenol often came up in textbooks and at the bench. Direct electrophilic substitution—chlorine gas, iron catalyst, a controlled temperature bath—yields plenty of 4-chlorophenol alongside side products. Another option that showed up in industry literature involved alkaline hydrolysis of 1,4-dichlorobenzene, but most small-scale syntheses just stuck to straight phenol chlorination. Production at scale balanced reactor temperatures, reactant ratios, and tight separation to keep the outputs pure. Today’s manufacturing focuses not just on yield, but waste management and containment, since byproducts spell trouble for groundwater and disposal.

Chemical Reactions & Modifications

At the chemistry bench, 4-chlorophenol behaves like an old workhorse: plenty reactive if pushed, yet sturdy. The hydroxyl group invites ether or ester formation; the aromatic ring allows further halogenation or nitration. Reduction of the ring or displacement at the chlorine position unlocks yet more derivatives. Its role as a building block for biocides and dyes means modifications—nucleophilic substitutions, oxidative couplings, and functional group transformations—land it in diverse families of pharmaceuticals, pigments, and farm chemicals. Every creative chemical pathway I saw, someone found a spot for 4-chlorophenol as a stepping stone, underlining how foundational this seemingly simple aromatic compound really is in big synthetic schemes.

Synonyms & Product Names

Chemical dealers and old manuals rattle off a list of synonyms that crop up every time the chemical changes hands or gets poured into a new label: para-chlorophenol, 1-hydroxy-4-chlorobenzene, 4-CP, and sometimes p-chlorophenol. In drug development, these aliases make record-tracing tougher—the same compound hides under many names. For researchers, remembering that these versions all mean the same thing avoids confusion and errors in handling or documentation—a lesson drilled in from the beginning of any chemical safety training.

Safety & Operational Standards

No one in an industrial setting takes 4-chlorophenol lightly. Every exposure scenario, from a splash to vapor inhalation, gets documented and rehearsed. My time around production lines convinced me that protocols matter: full PPE, exhaust hoods, spill kits ready to deploy. Long-term exposure studies point to eye, skin, and respiratory irritation, plus liver and kidney effects in repeated scenarios. Agencies like OSHA and the EPA keep a close grip, setting tight exposure limits and demanding robust containment and emergency routines. In my own experience, handling this chemical meant giving every procedure your full attention—nothing ruins your day like a dropped beaker or a glove breach with this compound.

Application Area

The reach of 4-chlorophenol stretches across more industries than most realize. Wood preservation stands out, where the chemical’s fungicidal profile holds off mold and rot. In public health, disinfectant formulations take advantage of its ability to wipe out microbes with stubborn resistance. Dye manufacturers rely on its chemistry when making certain fast blues and greens. Agrochemical production borrows from its phenolic power to anchor insecticides. Labs grab it as an intermediate in synthetic planning for a roster of medicines and research chemicals. The trouble with this versatility is the same compound that solves one problem often creates another for waste management and environmental health.

Research & Development

Discussions at industry conferences and in academic circles don’t hide from 4-chlorophenol’s baggage. Current R&D homes in on better catalytic systems for cleaner synthesis, smarter waste capture, and alternatives that swap in for halogenated phenols without the same persistent risks. A few researchers dig into bioremediation strategies, harnessing fungi or engineered bacteria to chop up residues clinging to soil and water. Analytical chemists work up new detection methods—GC-MS, HPLC, next-generation biosensors—to sniff out trace contamination in everything from river sediment to blood samples. These advances don’t come about without input from toxicologists, public health officials, and frontline plant workers all sharing what works and what falls short in real-world trials.

Toxicity Research

No matter the industrial promise, evidence stacks up against unchecked chlorophenol use. Animal studies chart clear toxicity at moderate doses—liver and kidney damage, metabolic interference, central nervous effects. Chronic occupational exposure, even at low levels, causes accumulated harm and raises cancer flags. Environmental monitoring picks up residues long after use stops, tracing downstream into aquatic life and moving up the food chain. Several water treatment plants struggle to fully degrade or filter this compound, which lingers far longer than many realize. Regulatory reviews keep pushing for stricter thresholds and more thorough risk assessments, a movement that industry grudgingly, but increasingly, accepts.

Future Prospects

Looking ahead, the chemical industry faces stark choices. Restricting 4-chlorophenol forces investment in greener chemistry—engineered alternatives, lower-impact synthetic routes, and far tighter lifecycle controls for persistent organochlorines. Sectors tied to wood treatment and disinfectants already feel pressure to clean up their act, whether by reformulating or switching away from chlorophenols. Smart regulation, stronger public health advocacy, and genuine corporate responsibility go a lot further than lip service. My own takeaway: any old chemical whose legacy cuts both ways—innovation and contamination—deserves close scrutiny and honest cost-benefit reckoning. The field moves forward the more uncomfortable truths about 4-chlorophenol get aired, and the more scientists, workers, and communities press for safer, smarter tools.




What are the main uses of 4-Chlorophenol?

What 4-Chlorophenol Means in Everyday Life

Walk down aisles packed with household cleaners or peek into supply rooms in hospitals, and it’s likely you’re seeing the end products of complex chemistry. 4-Chlorophenol packs more punch in these spaces than most folks realize. Its sharp, medicated scent hints at why manufacturers use it—its ability to kill bacteria and keep things sanitary. Years ago, I spent a few summers stacking shelves in a hardware store, where certain surface cleaners always carried warnings about strong chemicals. These warnings aren’t there by accident.

Industrial Cleaners and Disinfectants

Chemists figured out long ago that phenols stall the growth of germs, and adding chlorine amps up that action. In making disinfectants, detergent-makers reach for 4-Chlorophenol to crank up the germ-fighting power. It’s part of many products meant for cleaning toilets, hospital floors, and even dental offices. When you walk into a freshly mopped hospital hallway, there’s a decent chance that some form of chlorophenol is at work. Government agencies point at its effectiveness, and companies have done studies showing it whacks bacteria, molds, and some viruses better than plenty of older cleaning agents.

Starting Point for Bigger Molecules

The chemistry world relies on building blocks, and 4-Chlorophenol serves as one of them. Making dyes for the textile trade or pesticides designed to guard crops often starts with turning this compound into more elaborate molecules. It doesn’t make headlines, but every cotton T-shirt or protected acre of farmland tells a hidden story powered by these chemical steps. Back in college, running simple labs taught me how even a single added chlorine atom changed the behavior of a molecule in unpredictable ways—important for fine-tuned industrial work.

Pesticides and Weed Killers

Big rows of crops fighting off insects or fungal invaders need sturdy defense, and some herbicides and fungicides build off of 4-Chlorophenol. Agribusiness spends serious money crafting sprays that keep food supply chains humming. The compound forms a backbone for chemicals that knock out weeds or spoilage organisms without taking down entire fields. There’s a balance here, because shifting away from these compounds isn’t easy—yet tighter rules on residue and run-off show the world keeps asking tough questions about what should be sprayed on food.

Makers of Dyes and Pharmaceuticals

People want color that lasts, whether it’s on fabrics or as part of inks, and 4-Chlorophenol steps in as a chemical precursor here. The colorfast dyes keeping shirts bright after dozens of washes often share roots with this molecule. Drug manufacturers also reach for it when synthesizing new medicines, searching for molecules that have just the right punch to treat illnesses.

Challenges and Safer Solutions

The sting in the tail comes from health hazards. 4-Chlorophenol can be toxic if handled carelessly, and its ability to linger in soil and water means it can pile up faster than nature can break it down. From a neighbor who works for the local water treatment plant, I learned that even tiny leaks or spills from factories can set off alarms. Worker safety demands personal protective gear and strong ventilation.

Cutting health risks isn’t simple. Stronger rules, smarter waste management, and greener chemistry all matter. Discovering alternatives means scientists try to match the disinfection and pest control power but with less chance of choking up rivers or risking factory workers’ health. In recent years, pressure from both consumers and regulators sped up the shift toward less-harmful compounds, but transitioning industries takes time.

Is 4-Chlorophenol hazardous to health?

A Closer Look at 4-Chlorophenol

4-Chlorophenol crops up in conversations among people who work around chemicals or live close to facilities using it. Found in making pesticides, dyes, and drugs, this substance doesn’t get much attention outside of industries. Once you step beyond plant fences and into the real world, stories start to pop up—workers with odd rashes, complaints of an odd stinging smell in tap water, or kids near a factory losing their appetite and feeling sick. The science behind these stories speaks volumes. Research from the National Institutes of Health points out that swallowing 4-Chlorophenol, breathing it in, or getting it on your skin can trigger irritation, headaches, nausea, and long-term effects nobody wants to see, like liver and kidney trouble. It’s also listed as a possible carcinogen, which means there’s a chance it could help start cancer in people.

Everyday Exposure: More Common Than You Think

Most folks don’t see themselves near chemical plants, so they tune out this kind of thing. But the catch is, 4-Chlorophenol doesn’t just stick to one spot. Runoff from factories can get into local streams and, in poorly run towns, into public water. Homeowners using certain weed killers, cleaners, or wood preservatives might bring this chemical into their garage or under the sink. With a boiling point not far above room temperature, fumes can spread while you’re spraying down some mold or treating the fence outside. You might not see it, but your nose will notice a sharp, medicinal odor—the kind that lingers.

Personal Experience and Practical Worries

The first time I came across 4-Chlorophenol, I was volunteering to clean up an abandoned lot behind a paint factory. Gloves and a mask kept part of it off me, but by the end of the day, a pounding headache and sore throat stuck around. Friends with jobs in maintenance or public utilities swap stories about skin turning red and patchy just from handling treated lumber or touching old equipment. People with existing health issues—like asthma or eczema—tend to react more. These chemicals, once in your neighborhood, don’t just wash away.

What Makes 4-Chlorophenol Different?

Unlike some household cleaners, 4-Chlorophenol can damage the body even at low levels if folks get exposed day after day. The Centers for Disease Control and Prevention highlights reports linking repeat exposure to muscle spasms, confusion, and even effects on unborn children. It clings to sediments in ponds and creeks, and some groundwater testing has picked it up long after a spill or plant closing. This longevity worries experts, especially since purification isn’t easy—charcoal and special resin might pull it out, but regular at-home filters won’t touch it. Kids playing near contaminated patches risk more than dirty shoes—they drag what gets on their skin back inside.

Building a Safer Environment

Basic fixes start with strict waste control at chemical plants and regular checks on public water. On a smaller scale, people at home should ditch old containers with faded labels and pick safer cleaners and herbicides. Protective gear—gloves, masks, goggles—shouldn’t just gather dust on work sites or in cleaning closets. Neighbors should push for fast cleanup of spills and honest reporting from factories. Schools and clinics can share fact sheets, teach kids to steer clear of colored puddles and strange smells, and encourage adults to ask questions about what’s drifting around their homes and workplaces. Real solutions grow out of recognizing problems, protecting each other, and not brushing off what a strange smell or rash might mean.

What are the storage and handling requirements for 4-Chlorophenol?

The Real Deal with 4-Chlorophenol

4-Chlorophenol carries a sharp odor you’ll remember, and its uses stretch from making pesticides to serving as a disinfectant. This chemical demands respect from anyone bringing it into a lab or factory. I’ve seen what ignoring the basics can do—strange stains, a lingering chemical sting in the air, sometimes an emergency trip to the eyewash station. Mistakes add up quickly.

Storage: Getting it Right

Let’s start with choice of storage space. You want something cool, dry, and well-ventilated, far from any direct sunlight. Heat speeds up decomposition, and with 4-Chlorophenol, that means toxic fumes—think hydrochloric acid and other nasties. You do not want anyone breathing those in. Keep it away from open flames, oxidizers, or strong bases, since those combinations are famous for disasters.

I remember a colleague who stacked containers too close to a window, thinking the area was “out of direct sun.” A warm afternoon changed the story. Labels faded, crystals formed inside the bottles, and a clean-up followed. Secure all containers tightly—plastic jugs do the job, but glass provides extra reassurance against leaks. Store on a spill tray. Even one drop can jumpstart corrosion, or worse, soak through shelving.

PPE Isn’t Optional

I’d say the right gear is a daily decision around 4-Chlorophenol. Gloves—nitrile or neoprene—keep skin safe. Don a lab coat or apron, along with goggles or a full face shield. A single splash causes skin burns and eye injury, and even small amounts hurt. A friend once called it “chemical paper cut times ten.” Gloves tear, lab coats get caught on edges, so inspect gear before every use.

Respiratory protection matters if you’re in a poorly ventilated area. With routine handling, you can taste the fumes in the back of your throat without a decent mask or proper airflow. Always use a fume hood or at least a strong local exhaust system. Studies from the National Institute for Occupational Safety and Health (NIOSH) stress how inhalation produces everything from headaches to organ damage.

Cleanup and Waste Disposal

Clean spills fast, but never solo. Have a spill kit with absorbents, but not with any organic material that can react. Keep sand or vermiculite close, not sawdust. Wipe up any residue with soap and water after capturing the main mess, then seal everything used for cleanup in labeled hazardous waste bins.

Diluting or pouring it down the drain breaks both state and federal law. Professional chemical waste disposal services remain the only real option. Many local governments increase spot checks at labs that handle phenols because a single release into the water table means trouble for an entire neighborhood.

Staying Ahead with Staff Training

In my time running safety meetings, hands-on practice always helps more than written protocols. Get everyone familiar with the Material Safety Data Sheet (MSDS) for 4-Chlorophenol. Walk through all possible incidents, from a broken bottle to a fire drill. A trained team keeps small mishaps from exploding into serious emergencies.

People trust you with their health every time they step into the workspace. Handling 4-Chlorophenol calls for vigilance, respect, and a little humility—nature can always surprise the complacent. Safe storage and strict handling habits go a long way, and nobody regrets going the extra step for peace of mind.

How should 4-Chlorophenol be disposed of safely?

Recognizing the Problem

Anyone who’s worked in a lab or manufacturing plant probably knows that 4-Chlorophenol doesn’t belong anywhere near regular trash or drains. Even though it’s found in disinfectants and some pesticides, this chemical carries a real risk for water systems and wildlife. Leaking it into drains or tossing it out with garbage ends up polluting rivers and disrupting aquatic life. Plus, it’s classified by the EPA as a hazardous substance. Mishandling it can lead to legal fines or harm workers and nearby communities. From experience, safety slips happen not because of bad intentions, but because people don’t get clear guidance.

Why Proper Handling Matters

When 4-Chlorophenol hits water, it lingers. Microbes struggle to break it down, and it doesn’t sit quietly in the background. Even small amounts can poison fish or contaminate drinking water. According to the Agency for Toxic Substances and Disease Registry, 4-Chlorophenol can cause burning sensations on skin and respiratory distress if breathed in. At high doses, it’s toxic to people and animals. Years ago, I saw a case where a forgotten bottle leaked, causing a big cleanup in a school. No one got hurt, but it brought home how easy it is for one slip to cause a cascade of headaches.

Getting Rid of 4-Chlorophenol Safely

Lab managers and anyone with leftover stock should start with the Material Safety Data Sheet. Every chemical has one, and this sheet lays out risks, spill response, and emergency contacts. Simple instructions often get missed, but they matter. Store containers tightly closed, away from acids or oxidizing agents, and in a well-ventilated area. Think ahead before moving a bottle—avoid glass-on-glass knocks, or stacking them where they might fall.

For disposal, no shortcut exists. Burning or dumping means breaking the law and endangering others. The best way involves sending containers to a licensed hazardous waste facility. Staff there use incinerators that hit high temperatures, which destroy the compound before it reaches the environment. Local waste disposal companies or municipal hazardous waste programs take small amounts from individuals. Most colleges and research centers have a central hazardous waste coordinator, and that person arranges pickups or drop-offs. I recall rounding up old solvents from our university labs every term. It took a couple hours, but we never had an incident that year.

Finding Better Systems

Some groups hold regular hazardous waste collection days. These events let households drop off old chemicals, electronics, and medicines all at once. The key is labeling everything clearly and keeping original packaging. Getting into the habit of logging chemicals helps labs cut down on clutter and reminds people to use what’s already on hand instead of ordering more. During one audit I helped with, we located years-old supplies and sent them off before they became a problem. This type of culture grows from the ground up—clear instructions, practical reminders, and accountability.

Simple Steps Everyday

Everyone plays a role: chemists, students, janitors, contractors. If you spot an unmarked container or spill, speak up and report it. If you’re unsure about handling or disposal, don’t guess—contact your safety officer or local hazardous waste program. Schools and businesses that invest in staff training see fewer mistakes and spend less on cleanups long-term. Respecting chemical risks isn’t about paranoia, but common sense and responsibility to your neighbors.

What is the chemical structure and formula of 4-Chlorophenol?

Getting to Know the Molecule

4-Chlorophenol stands out in the large family of chlorinated phenols. Anyone who has spent time in a chemistry lab will recognize the sharp, distinctive odor and the sense of caution that comes along with it. Chlorophenols show up in a range of industries and applications, but each member in this group holds its own unique quirks. The "4" in its name refers to the position of the chlorine atom on the benzene ring, right across from the hydroxyl group. This specific arrangement has a real impact on both its reactivity and how it shows up in industrial uses.

Diving into the Structure

The core of 4-Chlorophenol is a benzene ring — six carbon atoms linked in a hexagonal shape, each connected by alternating single and double bonds. At the number four spot, counting from the hydroxyl group, a chlorine atom sits attached to the ring. This exact placement turns an otherwise typical phenol into a compound with its own stability, reactivity, and toxicity profile. The formula for 4-Chlorophenol is C6H5ClO, which sums up its basic ingredients: six carbons, five hydrogens, one chlorine, and one oxygen.

Why the Structure Matters

Chlorine packs a punch. Swapping a hydrogen for a chlorine atom changes a lot — it shifts electron distribution on the benzene ring and affects how this compound reacts in the environment or in industry. Lab technicians who prepare 4-Chlorophenol for synthesis know its chemical properties can encourage or block certain reactions. The hydroxyl group (an -OH) boosts water solubility, while chlorine adds weight and opens doors to further substitutions. That’s why it often serves as a building block in making pesticides, disinfectants, and dyes.

Health and Safety Risks

Exposure to chlorinated phenols can mean skin and respiratory irritation, and they easily slip into waterways or soil if not handled properly. In my experience around industrial waste treatment, managing runoff from any process using 4-Chlorophenol takes clear procedures and good chemistry know-how. Mismanagement leads to contamination, affecting soil organisms or even making its way up the food chain. Public health agencies keep a watch on these chemicals for good reason.

Environmental Impact

4-Chlorophenol shows up in polluted wastewater, a result of its use in large-scale chemical manufacturing. Its persistence in the environment comes from that strong benzene ring, and the chlorine atom increases its resistance to breakdown. Bacteria can metabolize some chlorinated aromatics, but the process moves slowly. This slow degradation brings up real concerns for ecosystems downstream from chemical plants. Cleanup processes often rely on advanced oxidation or specialized bioremediation.

What Can Be Done

Chemical engineers and environmental scientists look to greener synthesis methods and safer alternatives for disinfection or production. Programs that use activated carbon filtration or promote breakdown by sunlight (photolysis) offer solid ways to reduce environmental loads. In regulatory circles, setting discharge limits for operators of chemical plants and boosting monitoring usually bring results. My own takeaway: the more we understand the links between structure and behavior, the better we can make choices that balance industrial need with public security.

Quick Facts

  • Chemical formula: C6H5ClO
  • Structure: Benzene ring with -OH group at carbon 1 and -Cl at carbon 4
  • Molecular weight: About 128.56 g/mol
  • Applications: Intermediate for dyes, antiseptics, pesticides
  • Hazard profile: Toxic, irritant, environmental persistence

4-Chlorophenol
Names
Preferred IUPAC name 4-Chlorophenol
Other names p-Chlorophenol
4-Hydroxychlorobenzene
PCP
p-Chlorohydroxybenzene
Pronunciation /ˈklɔːrəˌfiːnɒl/
Identifiers
CAS Number 106-48-9
Beilstein Reference 1362462
ChEBI CHEBI:16240
ChEMBL CHEMBL1358
ChemSpider 6917
DrugBank DB04260
ECHA InfoCard ECHA InfoCard: 100.003.264
EC Number 4.99.1.1
Gmelin Reference Gmelin Reference: **8283**
KEGG C01415
MeSH D002683
PubChem CID 955
RTECS number SN4300000
UNII K4PN4U1033
UN number UN2020
Properties
Chemical formula C6H5ClO
Molar mass 128.56 g/mol
Appearance white crystalline solid
Odor Strong, penetrating, medicinal
Density 1.31 g/cm³
Solubility in water 20 g/L (20 °C)
log P 1.95
Vapor pressure 0.16 mmHg (25°C)
Acidity (pKa) 9.38
Basicity (pKb) 15.0
Magnetic susceptibility (χ) -60.5e-6 cm³/mol
Refractive index (nD) 1.556
Viscosity 2.63 mPa·s (at 25 °C)
Dipole moment 1.61 D
Thermochemistry
Std molar entropy (S⦵298) 108.7 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) -27.7 kJ/mol
Std enthalpy of combustion (ΔcH⦵298) -3221.0 kJ/mol
Pharmacology
ATC code D08AE01
Hazards
Main hazards Toxic if swallowed, in contact with skin or if inhaled; Causes severe skin burns and eye damage; Harmful to aquatic life with long lasting effects
GHS labelling GHS02, GHS05, GHS06
Pictograms GHS05,GHS06
Signal word Danger
Hazard statements H301 + H311 + H331: Toxic if swallowed, in contact with skin or if inhaled. H373: May cause damage to organs through prolonged or repeated exposure. H411: Toxic to aquatic life with long lasting effects.
Precautionary statements P260, P280, P301+P310, P305+P351+P338, P310
NFPA 704 (fire diamond) 3-2-0-A
Flash point 79°C
Autoignition temperature 230°C
Explosive limits Explosive limits: 2.8–10.0%
Lethal dose or concentration LD50 oral rat 450 mg/kg
LD50 (median dose) LD50 (median dose): 450 mg/kg (oral, rat)
NIOSH PC14000
PEL (Permissible) 5 ppm
REL (Recommended) 0.1 mg/L
IDLH (Immediate danger) 40 ppm
Related compounds
Related compounds Phenol
2-Chlorophenol
3-Chlorophenol
2,4-Dichlorophenol
4-Bromophenol
4-Fluorophenol
4-Nitrophenol