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The Real Impact of Phenol Salts: Echoes Across Time and Industry

The Road Phenol Salts Have Traveled

Dig deep into any modern laboratory or industrial setup, chances are you'll run into phenol salts sooner rather than later. Their journey didn’t start with a bang but a careful crawl through years of chemical tinkering and observation. Tracing back to the late 19th century, chemists began fiddling with the phenol molecule, hunting for ways to tame its reactive nature. The idea of pairing it with different cations grew out of practical headaches. Pure phenol proved too volatile and toxic for routine use, so reacting it with bases like sodium hydroxide, potassium carbonate, and others gave rise to a family of less volatile, more manageable compounds: phenolates, sodium phenoxide, potassium phenolate, and so on.

Personal stories with phenol salts often begin in college chemistry labs, where strong odors and safety briefs etched their not-so-gentle power in memory. Only with time did those early lessons sink in—every capped flask held more than a few lines in a textbook. Decades of industrial research followed, and the uses for phenol salts multiplied just as the understanding of their hazards deepened. Across industries—from resins and plastics to pharmaceuticals and dyes—many household goods owe something to the modest story of a salt paired up with phenol.

What Stands Out About Phenol Salts

Most can recognize phenol by its distinct, biting aroma, but its salts often pass by unnoticed, nestled as off-white powders or crystallized solids depending on what metal joins the mix. Solubility jumps dramatically with salt formation, especially in water. That change alone has made them invaluable in processes where mixing is half the battle. Compared with raw phenol, these salts give you a handle—less volatility, easier transportation, and faster reactivity in some synthetic routes.

The basic chemistry sits on clear ground: phenol reacts with a suitable base—the strong kind, like sodium or potassium hydroxide—and swaps a hydrogen from the hydroxyl group for a metal ion, producing water alongside the new salt. The resulting compounds take on new chemical behavior, turning into decent nucleophiles thanks to the negative charge left behind on the oxygen. In practice, this means they jump into reactions that phenol itself would hesitate to join, unlocking broader applications that raw phenol couldn't handle on its own.

Labels and Technical Numbers Aren’t Just for Show

Anyone used to handling chemicals gets an early lesson in reading labels meticulously. With phenol salts, this habit becomes more than a convenience; it’s essential for safe operation. Each container tells a story with chemical identifiers, purity levels, storage recommendations, and safety warnings that aren't just regulatory theatre. Poor labeling backfires. Tightly regulated environments, such as pharmaceutical or food-related production lines, use these specifications to dodge disasters: moisture sensitivity can degrade quality, and even traces of impurity can spoil an entire batch. Regulatory standards don’t come out of thin air—agencies such as OSHA, REACH, and the EPA settle on toxicity limits for phenol salts by sifting through years of hard-won toxicological data.

From Lab Bench to Factory Floor: Getting Ready and Making Changes

Making phenol salts isn’t a high drama affair in theory, though scale brings its own set of risks. In small settings, the process is straightforward: dissolving phenol in a basic aqueous solution, watching the reaction fizz gently as the salt forms. Large-scale production ramps the risks—containment becomes harder, and purity more demanding. With sodium phenoxide or potassium phenolate, industrial players often optimize reaction times and temperatures to boost yield, minimize byproducts, and prevent runaway reactions. It’s hands-on chemistry, and the tweaks at this stage can set an operation apart from competitors.

Once in salt form, phenol’s chemistry flexes in new directions. These compounds react as nucleophiles, opening the door to etherifications, esterifications, and arylations that form the backbone for materials like epoxy resins, pharmaceuticals, and dyes. The ability to swap in different cations—playing with lithium or calcium salts, for instance—gives manufacturers tuning dials for solubility, melting point, and even reactivity.

Names and Crossroads in a Crowded Market

Inside the chemical supply trade, phenol salts don’t stick to a single name. Walk through catalogues and you'll see sodium phenoxide, potassium phenolate, lithium phenolate, and more. Each synonym signals subtle differences in reactivity or process suitability, and missing these distinctions can cost a project its edge. These salts turn up again in the vocabulary of polymer chemists, perfumers, textile innovators, and pharmaceutical developers—each with their favored alias, blending utility with tradition.

Working Safely: Lessons Learned, Standards Evolve

Handling phenol salts means keeping sharp. They don’t pack the infamous punch of pure phenol, but they can still irritate, burn, or sensitize skin on contact. Splash risk asks for eye protection, gloves, and splash shields; inhaling dust in an industrial setting can turn a routine day into a medical emergency. Storage recommendations—low temperature, dry environment, sealed containers—come not from faceless bureaucracy but from the frustration and injury that inevitably follow sloppy habits. Decades of accident reports and occupational medicine show how standards change only after something goes wrong—tighter ventilation protocols, stricter exposure limits, and regular air sampling have all become a mainstay where these salts see heavy use.

Applications That Weave the Everyday

The reach of phenol salts goes well beyond the laboratory. Epoxy resins start out with these salts, their molecular structure shaping everything from electronics casings to high-performance adhesives. Visit a pharmaceutical plant and you’ll find phenolates in drug synthesis, often part of core steps where basic conditions demand a salt over an acid. Textile and dye industries lean on phenol salts too, using them to create vibrant, stable colors that don’t fade after a few washes.

Personal experience in research settings reveals just how adaptable these salts can be. During an undergrad project on epoxy curing agents, the versatility of sodium phenoxide left a real impression—quick, reliable, and tuned with a simple swap of cation or the base solvent. Industrial chemists gravitate toward these traits for a reason. The consistency of yield, the predictable behavior, and the comparative safety give them an edge, making large-scale applications feasible without needing extensive retooling or exotic containment.

What Pushes Research Forward

Researchers fixate on phenol salts for good reason—their chemical leverage is huge, especially in organic synthesis and materials science. New catalysts, improved polymers, and even eco-friendlier production methods depend on tweaking these chemistry workhorses. Some research aims to create functionalized phenolates, swapping substituents on the aromatic ring to pull the molecule’s properties in new directions—improving selectivity, increasing reactivity, or cutting toxicity. Large academic consortia and industrial R&D centers pour time and funding into these experiments, hoping to patent the next must-have intermediate for drug, resin, or pigment manufacture.

Efforts to reduce the hazards of phenol salts move forward too. Alternative solvent systems, solid-state synthesis routes, and catalysts that lower process temperatures or avoid dangerous byproducts all drive the field ahead. Each small breakthrough—lower emissions, higher purity, faster reactions—can ripple out through global supply chains. We've seen major shifts in production methods just from replacing one base with another, or from engineering closed-loop manufacturing systems to trap waste and unreacted materials.

Toxicity: Unwanted Shadows That Don’t Let Go

Phenol’s hazards haven’t disappeared in salt form. Toxicology studies track breakdown products, assess how quickly they travel through the body, and examine if they cause chronic health problems. Acute exposures bring out the usual list—skin irritation, burns, and systemic toxicity if inhaled or ingested. Longer-term risks, including possible impacts on liver and kidney function, have prompted regular updates to workplace exposure limits. Regulations have grown teeth as more public health data rolls in.

Crossing into environmental health, questions linger about how these salts behave once washed into waterways or soils. Some break down quickly, but others stick around, binding to sediments or moving up the food chain. Wastewater treatment plants flag them for removal, since traces can harm aquatic life and disrupt biological treatment processes. Ecology experts point out that the pursuit of better, safer alternatives depends as much on environmental monitoring as on clever new chemistry.

Looking Forward: Paths Worth Taking

The future for phenol salts holds space for upgrades on every front. Greener production—using less energy, safer reactants, and solvents that don't harm ecosystems—sits high up on research agendas. Demand for high-performance polymers and precision pharmaceuticals drives ongoing innovation; every year reveals new applications that lean harder on the reliability and versatility of these molecules. Automated reactors and data-driven process screening offer potential to shrink waste, boost yields, and flag trouble before a batch goes off course.

Industry standards for labeling, storage, and safety will tighten as new toxicology and environmental data surface. Labs will keep hunting down ways to switch to less hazardous alternatives, or at least contain and recycle waste more effectively. Chemical education continues to stress hands-on learning about these classic substances—knowing their limits, strengths, and the human mistakes that shaped their use over the years. Phenol salts may not demand the spotlight, but their quiet influence keeps engineering and manufacturing running more smoothly than most will ever notice.




What are the main uses of Phenol Salts?

The Core Roles in Disinfection

Over the years, phenol salts found their ground in cleaning, not just at home, but across clinics, public washrooms, and factories. Mixed with water, these compounds help knock out harmful bacteria and fungi. Hospitals keep them in stockrooms for routine ward cleaning. I’ve seen custodial staff rely on phenolics when infectious diseases threaten to spread through surfaces and floors. Surfaces that see steady contact—from clinic exam tables to public toilets—benefit from these salts’ reliable kill-rate against tough germs, including those causing tuberculosis and staph infections. The truth is, many commercial and institutional cleaners started using phenol-based agents long before modern quaternary ammonium blends became popular.

Bringing Chemistry to Industry

Textile mills and tanning units also turn to phenol salts. In wool scouring, these compounds suppress odorous bacteria and mold. Leather tanning relies on these salts not just to clean raw hides but to help preserve them, warding off spoilage before the valuable material gets processed further. These aren’t niche markets; globally, textile and leather demand never dips much, and without effective protection, whole batches end up ruined. Manufacturing runs on tight margins, and losing product to bacterial spoilage isn’t just waste—it hits jobs and raises costs for everyone down the supply chain.

Everyday Consumer Protection

Most people don’t realize phenolics guard household items too. Some mouthwashes still include small amounts of phenol-based ingredients as antiseptics. Certain sore throat sprays use diluted phenol salts for pain relief and infection control. While these direct uses stay tightly regulated, the reason they stick around is simple: they work, providing effective antimicrobial action right where it’s needed. Some old-school antiseptic creams in home medicine cabinets carry a light whiff of phenol, a reminder of its long history as a defense against minor injuries.

Water Systems and Agriculture

Water cooling towers in large buildings and power stations need steady protection from bacterial fouling. Phenol salts keep biofilms from building up on metal and concrete—places where mechanical scrubbing falls short. I’ve talked to building engineers who note how neglected cooling systems can turn into public health hazards if bacteria flourish unchecked. Agriculture, too, leans on these compounds for disinfecting animal pens and sheds, helping farmers keep livestock safe from disease outbreaks.

Looking Ahead: Health, Environment, and Safer Use

There’s no sidestepping the health risks. Phenol salts bring toxic fumes, especially in large quantities. I wore protective gloves and goggles in labs and cleaning jobs because skin contact can cause burns or worse. Overuse can spill into waterways, harming aquatic life. Regulators urge users to dilute properly, ventilate indoor areas, and never mix these compounds into drinking supplies. Scientists work on friendlier alternatives, but for now, sometimes a strong hand is still needed for high-risk environments. Companies have started pivoting to blends that cut down on off-gassing while keeping the potent germ-killing action, bringing better balance for workers and end-users. Smart use, protective gear, and strict controls on disposal underline responsible handling—this is how seasoned crews handle powerful industrial chemistry, earning public trust without waving away safety.

Are Phenol Salts safe for human contact or consumption?

Understanding Phenol Salts

Phenol salts pop up in many places, from science labs to cleaning supplies. Think of these as the result of mixing phenol, a strong-smelling chemical, with a base. Suddenly, you have a compound that looks calmer on paper but keeps some rough edges. Decades ago, I worked in a university chemistry lab, and I remember the sharp tang that hit my nose whenever someone unscrewed a phenol bottle. That sensation stuck with me because it meant extra caution was necessary. Over the years, I’d see phenol salts show up under different names and uses, sparking the same concern: just how safe are they?

Direct Contact and Human Safety

Most folks rarely bump into pure phenol salts outside a controlled setting. But cleaners, certain medications, and even preservatives sometimes contain ingredients drawn from these compounds. If you touch phenol salts, especially in concentrated form, the skin can burn, itch, or start to peel. I still remember an undergraduate’s hand after a spill during a particularly rushed experiment; the red, swollen patch matched what toxicology handbooks warned about. The problem isn’t just the visible surface reaction. Phenol and its salts can skate right through the skin and enter the bloodstream, causing headaches, sweating, rapid heartbeat, and, at worst, organ problems. It takes one serious spill to see why protective gloves become second nature in the lab.

Consumption: The Stark Warning Signs

Sometimes people ask if small amounts matter — after all, trace ingredients slip into medications and foods. Here’s the deal: phenol salts have no place in the human diet, and ingesting any significant amount can damage the digestive lining, kidneys, or nervous system. Poison control center data over the years points to rapid onset of symptoms like vomiting, breathing trouble, and confusion. Healthcare staff move fast in those cases.

On rare occasions, certain compound medicines have included phenol derivatives to fight bacteria or fungi. While the thinking behind those products was sound at the time, most have faded due to adverse side effects. Newer regulations toss out any hope of using phenol salts in foods or unregulated supplements. The FDA and the European Chemicals Agency treat them as hazardous for consumption, placing them under strict use requirements.

Real-World Solutions and Precautions

Deciding how to handle phenol salts safely comes down to simple habits. In the lab, I always reach for thick gloves and goggles. The industrial scene relies on full body suits and good ventilation. Home users, on the other hand, might get exposed through specialty cleaners. Scrutinize labels and keep such products locked away from kids. If a product contains a chemical name ending in “phenate” or “phenoxide,” it’s best to avoid direct skin contact and never allow it near food or drink.

Biodegradable alternatives fill shelves now, steering people away from hazardous chemicals. Even so, knowledge always trumps wishful thinking. If you suspect exposure or your skin burns after an accidental touch, quick washing and prompt medical attention matter much more than waiting for symptoms to develop.

Expert Consensus on Phenol Salts

Health agencies agree: phenol salts present risks that outweigh any minor benefits in cleaning or medicine. Use them only as directed, preferably only if you work in science, industry, or medicine where proper training backs up every step. Staying informed and cautious helps keep the dangers at bay.

How should Phenol Salts be stored and handled?

Understanding the Real Risks of Phenol Salts

Every lab worker remembers the sharp, pungent smell of phenols from their first week in chemistry class. These substances, including phenol salts, carry some notorious dangers you can’t ignore. Years of working alongside chemicals taught me respect for these compounds; too many times, I’ve watched gloves eaten through by carelessness. Phenol salts bring risk in a different form—both from their chemical reactivity and health hazards. These substances can burn skin, cause lasting nerve damage, or send toxic fumes into the lab’s air. Even trace contamination between containers can create a hazard. Handling gets safer only through strict, thoughtful storage and good habits taught by hard experience.

Learning Storage the Hard Way

No one forgets the time a poorly closed cap released an unmistakable smell throughout the storeroom. My supervisor back then reminded me it only takes one mistake to send someone to the hospital. Phenol salts thrive in cool, dry environments. Humidity encourages clumping and chemical breakdown; heat shortens shelf life and increases volatility. Glass containers with tight PTFE-lined seals stop leaks and stop fumes from slowly escaping. Labels need to scream out hazard warnings at a glance, not hide in the background. A quick grab for an unmarked jar could result in a health crisis, making clear labeling a matter of physical safety, not just paperwork.

The Role of Routine and Vigilance

People in the business of chemistry bring up PPE constantly, and there’s a reason. You reach for phenol salts, you reach for your gloves—nitrile or butyl, not latex. Safety goggles block the mist that floats up when the jar opens. The right fume hood means the difference between a safe shift and a trip to emergency care. Even simple things, like double-checking containers before and after use, keep fingers and lungs intact. Spills disappear under proper spill kits, not a rush of paper towels. Every lab should bolt eye wash stations and showers to the wall within running distance from benches where phenol salts make an appearance.

Why Experience Trumps Protocols

Written protocols matter, but real-world training makes them stick. After seeing a colleague brush their arm just once across a drop of phenol, and the resulting burn, you never forget the importance of rolling up sleeves or changing out of contaminated clothing immediately. Mixing phenol salts with acids or strong oxidizers risks sudden, violent reactions. Storage away from incompatible chemicals stands as an absolute rule—one that should never be bent, not even for convenience on a busy day. Cross-contamination ends up more likely than anyone expects; designating shelves specifically for these substances has saved more than one workspace from disaster.

Simple Solutions that Make Labs Safer

Some ideas come from listening to the people who use these substances every single day. Safety audits, run by staff and not just management, find problems no checklist ever predicts. Education keeps new hires from repeating old mistakes. I learned, early on, to report even small leaks or odd smells right away—better ten false alarms than one ignored incident. Manufacturers should always provide updated data sheets, and labs who keep digital copies accessible encourage people to actually read them before use.

It helps to approach phenol salts with a mindset of preparation, not routine. Simple discipline—gloves on every time, label checks twice, containers opened only in a fume hood—does more to protect people than any locked cabinet. For me, learning from incidents and never assuming “it won’t happen here” has made the difference between risk and safe, steady work in a setting where danger is always one small slip away.

What is the chemical composition of Phenol Salts?

Looking at What Forms Phenol Salts

Anyone who’s handled cleaning supplies, pharmaceuticals, or industrial chemicals has likely crossed paths with phenol in some shape. Mix phenol with a base—think sodium hydroxide or potassium hydroxide—and the result is a phenol salt. The big name here is sodium phenoxide (chemical formula: C6H5ONa). Simply put, phenol drops its hydrogen atom from the hydroxyl group, which jumps ship for a sodium ion, creating this salt. Potassium phenoxide, C6H5OK, works the same way with potassium.

Why the Chemical Details Matter

For decades, I’ve seen chemists and pharmacists turn to phenol salts due to their stability and solubility. Take sodium phenoxide, for example. It’s made from phenol (C6H5OH) and sodium hydroxide (NaOH). One reacts with the other in water, creating C6H5ONa and water (H2O). The process seems straightforward, but it highlights an important change: the acidity of the original phenol gets cut down, turning it into an easier molecule for further work, be it making dyes, resins, or drugs.

Real-World Use and the Value of the Right Salt

Most people don’t realize phenol started as an antiseptic and now branches out to everything from sunscreen to medicine. Its salts aren’t just by-products; they show up as starting points for more advanced chemistry. For example, in organic labs, you’ll see sodium phenoxide teaming up with alkyl halides to build ethers—a core step for making pain relievers, anesthetics, and even herbicides. Without that salt, this reaction needs more energy and delivers less product.

In the dye world, potassium phenoxide and sodium phenoxide help anchor colors to textiles. I watched an old friend, a textile chemist, rely on them to avoid color fade and waste—little tweaks here can save millions and keep clothes out of landfills that extra year. These are changes that, on a practical level, mean lower costs for manufacturers and more durable clothing for shoppers.

Safety and Disposal Challenges

The chemical structure, packed with a reactive phenoxide ion, means you get both utility and a headache. In the workplace, sodium phenoxide solutions need to stay away from skin and eyes, requiring gloves and glasses. Spills can’t get washed down the drain, either. Once I saw a plant fined by regulators for not neutralizing phenol salt waste—local rivers still carry the scars. In the lab and on the shop floor, standards from the Occupational Safety and Health Administration (OSHA) and the Environmental Protection Agency (EPA) spell out how to handle, store, and dispose of these chemicals safely.

Moving Toward Green Chemistry

As more industries switch to sustainable routines, the focus lands on how to make and use phenol salts with a smaller impact. Researchers are testing biodegradable alternatives to traditional bases, inventing cleaner synthesis steps, and hunting for recycling options. Some companies install closed-loop systems, catching every drop of phenol for future batches. The drive for safer, greener chemicals doesn’t just tick a regulatory box—it keeps workers healthy and builds trust with customers who want cleaner products.

Can Phenol Salts be mixed with other chemicals?

Why Phenol Salts Matter

Phenol salts show up in labs, industry, and sometimes even in cleaning solutions that sit under the kitchen sink. They’re pretty reactive, and that’s what makes the question about mixing them with other chemicals a real one, not just a bit of classroom chemistry trivia. Over the years, I’ve watched good-intentioned folks learn the hard way that mixing “safe” chemicals doesn’t always end well. Never assume two compounds can get tossed together without a second thought—especially when it comes to phenol salts.

Mixing: Fact and Real-World Experience

Chemists and researchers tend to pair chemicals for a reason, often looking to create something useful or to neutralize a dangerous ingredient. With phenol salts, the major worry isn’t just about what you’re trying to make, but also about what you might accidentally create. Phenol salts, including sodium phenoxide, react with acids, oxidizers, and even some metals. For example, dump some phenol salts into a strong acid like hydrochloric, and you’ll likely get back phenol—plus heat, and possibly some dangerous fumes. It’s chemistry, but it’s also common sense.

Safety Isn’t Optional

Mixing phenol salts doesn’t always mean trouble, but trouble loves to visit people who skip safety steps. Researchers at the American Chemical Society and the CDC have highlighted repeated accidents involving improper mixing in both industrial and home settings. Phenol itself can seriously mess up your skin or breathing. Its salts may seem less intense, but add the wrong chemical and you turn a stable salt into a risky mixture. Gases that release from mixing with nitrites, for example, can be quietly toxic before anyone realizes. That’s not a lab story; that’s real spills and near-misses I’ve seen with my own eyes.

Wider Ripples: Environmental and Health Risks

Dumping phenol salts into rivers or sewers alongside other cleaning products creates a dangerous stew that water treatment plants struggle to handle. Phenols can kill fish, harm plants, and hang around in the environment far longer than many realize. Greenpeace and EPA reports tell the same story: chemical mixing rarely stays in the lab. Back in 2012, a small plant near my old neighborhood sent untreated water containing phenol residues into the runoff. The smell was unforgettable, and so was the impact on the local creek.

What Can Actually Help

Mixing chemicals safely starts before the bottles ever leave the shelf. Labels make a good start, but real safety comes from training. Fact sheets, safety data sheets (SDS), and resources from OSHA lay out dangers clearly—assuming people care to read and follow the directions. Ventilation, gloves, goggles, and slow, cautious mixing with constant stirring cut risks. For anyone working outside a research lab, it makes sense to avoid mixing phenol salts unless you have spoken directly to a professional chemist or checked updated resources from reputable agencies like the CDC, EPA, or ACS.

Final Thoughts

In every job or home experiment involving chemicals, respecting their risks isn’t just about rules—it’s about making sure nobody lands in the emergency room. Phenol salts get used for good reasons, but mixing them with other chemicals asks for accidents unless every step gets a second look. Sometimes, the best solution is skipping the mix entirely. In this case, “better safe than sorry” isn’t just old advice—it’s the smartest approach to phenol salts and every chemical on the shelf.

Phenol Salts
Names
Preferred IUPAC name Phenolates
Other names Liquified phenol
Modified carbolic acid
Pronunciation /ˈfiː.nɒl sɒlts/
Identifiers
CAS Number 8006-93-7
Beilstein Reference 1900889
ChEBI CHEBI:25885
ChEMBL CHEMBL3297486
ChemSpider 3784
DrugBank DB11147
ECHA InfoCard ECHA InfoCard: 03-2119432737-37-0000
EC Number 232-593-9
Gmelin Reference 811
KEGG C01409
MeSH D010650
PubChem CID 996
RTECS number SJ3325000
UNII 72644K2U5K
UN number UN2821
Properties
Chemical formula C6H5ONa
Molar mass 94.11 g/mol
Appearance White crystalline powder
Odor sweet, tar-like
Density 1.2 g/cm3
Solubility in water soluble
log P 4.7
Vapor pressure Negligible
Acidity (pKa) 9.9
Basicity (pKb) 9.9
Magnetic susceptibility (χ) +3700.0e-6 cm³/mol
Refractive index (nD) 1.501
Dipole moment 6.9 D
Thermochemistry
Std molar entropy (S⦵298) 109.8 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) -322.1
Std enthalpy of combustion (ΔcH⦵298) -3223.7 kJ/mol
Pharmacology
ATC code R02AA19
Hazards
Main hazards Causes severe skin burns and eye damage. Harmful if swallowed or inhaled. Toxic to aquatic life.
GHS labelling GHS02, GHS06, GHS08
Pictograms GHS05,GHS06
Signal word Danger
Hazard statements H301 + H311 + H331: Toxic if swallowed, in contact with skin or if inhaled. H314: Causes severe skin burns and eye damage. H373: May cause damage to organs through prolonged or repeated exposure.
Precautionary statements P264, P273, P280, P301+P312, P302+P352, P305+P351+P338, P332+P313, P337+P313, P362+P364, P501
NFPA 704 (fire diamond) 3-0-2-Acid
Flash point No flash point
Autoignition temperature 715°F (380°C)
Lethal dose or concentration LD₅₀ oral (rat): 317 mg/kg
LD50 (median dose) LD50 (median dose): 0.5 g/kg (oral, rat)
NIOSH SJ5075000
PEL (Permissible) 5 ppm
REL (Recommended) 0.5 ppm
IDLH (Immediate danger) 250 ppm
Related compounds
Related compounds Sodium phenoxide
Potassium phenoxide
Calcium phenoxide
Phenolate ions
Alkali metal phenoxides