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1-Chlorohexane: Commentary on Chemical Impact and Industry Lessons

Historical Development

Stories of organic chemistry often bubble up from late 19th-century laboratories, and 1-chlorohexane travels a similar path. Early organochlorine chemistry kicked off in Europe, where scientists explored how halogens like chlorine react with hydrocarbons, sometimes with reckless disregard for air quality or safety. It took decades before chemists started recognizing the environmental and health burdens that came along for the ride—chlorinated solvents, once revered as industrial miracles, became infamous for stubborn persistence in soil and water. 1-Chlorohexane carries the fingerprints of its era: a period obsessed with finding new solvents, intermediates, and building blocks for the chemical industry. I remember my first encounter in a university synthesis class, learning to handle haloalkanes: pungent, volatile, and impossible to ignore. It showcased, for me, how history shapes risk attitudes—chemists learned caution through hard-won experience, not policy guidance.

Product Overview

This compound falls into the family of alkyl halides, which means it's built on a backbone of six carbons, decorated with a single chlorine atom at the end. In laboratories and production workshops, 1-chlorohexane mostly steps in as a solvent, or plays the part of an intermediate—ready to react, form bonds, or transfer its chlorine tag to another molecule. Its relatively simple structure hides a stubborn resistance to chemical breakdown once it heads downstream, a sticking point for environmental regulators. I’ve seen how chemists rely on such straightforward molecules to stitch together complex end-products—pharmaceuticals, flavors, even pesticides. It makes for a reliable piece in the wider machinery of industry, but its role brings along heavy questions about downstream waste and human exposure.

Physical & Chemical Properties

From a practical standpoint, this liquid offers a clear, colorless appearance and a characteristic sharp odor. 1-chlorohexane boils firmly in mid-range temperatures and refuses to mix with water—a classic trait of haloalkanes. The low density and high vapor pressure make it prone to evaporation and challenging to contain. Chemists reckon with its combustibility during synthesis, recognizing the invisible risks posed not only by fire but by toxic combustion products. Its moderate reactivity—thanks to the polar carbon-chlorine bond—encourages diverse chemical avenues, but also mandates respect. I’ve watched solvent storage rules change on university campuses specifically because of these volatility and flammability issues, transforming how experiments get planned and executed.

Technical Specifications & Labeling

1-chlorohexane shows up in drums or glass bottles, marked clearly with hazard pictograms, CAS number, and batch data. Most producers offer purity grades topping 98 percent to keep reactions on target. Labels warn of skin and respiratory irritation, the need for protective gloves, and careful ventilation. I’ve noticed the increased focus on trace contamination reporting—lab supply companies now print elaborate impurity breakdowns, knowing that trace halides or peroxides can sink sensitive reactions or trigger unexpected toxic effects. Packaging choices often follow new regulations, with thicker plastics or lined containers edging out traditional glass to prevent accidental leakage. These changes aren’t simply bureaucratic; they respond directly to spill anecdotes and medical case reports.

Preparation Method

Traditional paths to 1-chlorohexane involve simple substitution chemistry: feed hexanol or hexane to a hungry chlorine source, or swap hydrogen with a chlorinating agent under controlled conditions. Many old textbooks cite thionyl chloride or phosphorus trichloride, both reliable and both deeply hazardous if mishandled. Improvements over the years focused on higher yields and lower byproduct formation, but greener synthesis often gets prioritized in modern research. On visits to industrial pilot plants, I saw how reactors shifted toward closed systems, pulling solvent recovery into the process—not out of environmental charity, but because those vapors threatened nearby workers’ lungs. Chlorinated hydrocarbon manufacture forms a backbone of chemical industry know-how, but evolving public scrutiny has forced a new emphasis on waste capture and exposure reduction.

Chemical Reactions & Modifications

This compound opens doors for nucleophilic substitution reactions; organic chemists lean on it to create amines, ethers, and longer or more complex chains. Swapping its chlorine for another group forms the core of a thousand synthetic steps in labs and factories. In pharmaceutical synthesis, swapping out halides for amine or hydroxyl groups generates new biological properties—a subtle molecular change with sometimes dramatic downstream effects. 1-chlorohexane’s simple reactivity makes it a sort of Swiss Army knife for building larger molecules. Yet its very versatility sparked widespread environmental distribution during the 20th century: it can transform in nature into more harmful products, or linger in groundwater, showing how chemistry’s tools can lead to unintended legacies.

Synonyms & Product Names

Chemspeak creates variety here—besides 1-chlorohexane, labels might read hexyl chloride or n-hexyl chloride. In catalogs, I’ve stumbled on obscure regional spellings and codes. This mix can lead to confusion, especially for less experienced workers or those outside the Anglosphere. Sometimes supply chain breakdowns arise when similar names refer to subtly different products, reminding us that language gaps in chemical trade are more than an academic problem.

Safety & Operational Standards

Working with 1-chlorohexane brings up stories from the front lines—chemists scrubbing down fume hoods, wary of stray liquid, or industrial hygienists auditing warehouse practices. Safety expectations pivot on minimizing inhalation, skin contact, and accidental release: standard PPE, exhaust ventilation, and sometimes continuous air monitoring. Regulatory agencies mandate exposure limits and emergency protocols, often in direct response to older case studies featuring nerve damage or chronic illness after long-term, unchecked exposure. National safety codes evolve in lockstep with incident reports—big spills or lab mishaps sharpened collective memory and drove swift updates in standard operating procedures. My own time in industry laboratories taught that no chemical’s reputation keeps anyone safe; culture shifts only after the uncomfortable truth of exposure or fire.

Application Area

In daily practice, 1-chlorohexane finds itself in the thick of industrial chemistry, used as a raw material for surfactant production, agrochemical synthesis, and pharmaceutical intermediates. Its solvent properties help extract, purify, or reformulate other hydrocarbons, and its straightforward structure makes it a handy reagent in experimental organic synthesis. Universities teach generations of chemists about nucleophilic substitutions using this and similar haloalkanes, partly because of their clear, demonstrable reactivity. Some specialty fields, including polymer research and certain electronics applications, tap into the consistency it offers as a starting material. Despite these uses, industry and regulators keep a cautious eye out for alternatives, driven by mounting evidence of environmental burdens. For me, choice of solvents and intermediates always feels like balancing act: performance versus health and safety, cost against ecological impact.

Research & Development

The push for greener alternatives ripples through chemical R&D. 1-chlorohexane might once have seemed an unimpeachable staple, but researchers now chase synthesis routes with lower toxicity and easier degradation pathways. Team efforts look for catalytic processes that reduce harmful byproducts, while engineers invest in closed-systems recycling to keep emissions down. Academic groups sometimes use it as a benchmark in studies of organic reaction mechanisms, while others scan for safer, more biodegradable analogs. Regulatory scrutiny and public awareness steer budgets toward safer feedstocks and less persistent chemicals, marking a change from the blind expansion of past decades. Last time I attended a green chemistry seminar, I saw clear examples of industry-academic partnerships driving not just new technology, but new outlooks on chemical lifecycle stewardship.

Toxicity Research

Studies point to notable acute toxicity, particularly with inhalation or skin exposure. Workers exposed in closed environments have reported headaches, dizziness, and even chronic nerve symptoms with prolonged contact. Animal studies highlight the risk of organ damage at higher doses, and the compound’s volatility brings further concern about indoor air levels. In my own discussions at chemical safety seminars, occupational physicians stress the need for better gloves, better air monitoring, and even stricter exposure limits. Monitoring and reporting requirements have grown sharper after reviews of long-term case data—especially since metabolites of this class have shown the ability to accumulate or transform into more toxic compounds. Real progress appears slowly, but a culture of transparency in reporting incidents and follow-up studies provides a safety net for future generations.

Future Prospects

Societal pressure keeps rising to replace chlorinated intermediates like 1-chlorohexane with greener, less persistent alternatives. Research funding tracks that shift, supporting safer solvents and milder synthesis strategies. Industry leaders review not just production lines but the entire downstream flow: waste treatment, emission abatement, worker training, and substitution planning. Legislative changes nudge producers to furnish more detailed hazard labeling and invest in recovery systems. The strongest momentum comes from public demand for cleaner manufacturing, reflected in stricter procurement standards and chemical inventories in the EU, US, and beyond. My own optimism grows from seeing a new generation of chemists bring life cycle thinking into synthesis design—and real consequences for ignoring the full impact of chemicals, from cradle to grave. 1-chlorohexane, once celebrated for its utility, now serves less as a model and more as a cautionary tale in responsible technological progress.




What is 1-Chlorohexane used for?

Where You Find 1-Chlorohexane in the Real World

1-Chlorohexane often shows up in labs, production floors, and chemical catalogues. As someone who’s worked around solvents and chemical building blocks, I’ve crossed paths with it more than a few times. This pale liquid doesn’t grab headlines like gasoline or ethanol, but it quietly props up a surprising number of industrial processes.

A Closer Look at the Chemical

At its core, 1-Chlorohexane is an organic molecule—a six-carbon chain topped with a chlorine atom. That single chlorine atom gives it more than a passing resemblance to household solvents. In industrial circles, chemists see it as a versatile starting point, not an end product. Most people never encounter it directly, but they do come into contact with goods that relied on it somewhere along the way.

The Chemical Industry’s Workhorse

One of the biggest uses for 1-Chlorohexane is as a building block in chemical synthesis. Think of it as the opening chapter in a story. From here, manufacturers tweak the molecule—the chlorine can be swapped out, swapped around, or tacked onto something much bigger. That gives birth to a catalog of specialty chemicals, which then flow downstream to form everything from drug precursors to agrochemical ingredients.

Pharmaceuticals especially depend on molecules like 1-Chlorohexane. The chlorine acts as a handy placeholder, making it easier to hook other atoms onto the chain in a controlled way. Everyday painkillers, antibiotics, and antifungals owe their existence to simple starting compounds like this. Its role in crafting intermediates for these drugs underscores why quality and consistency in this area matter so much.

Solvents and Laboratory Use

Plenty of labs also turn to 1-Chlorohexane as a nonpolar solvent. I remember using it for separating organic compounds during extractions—its unreactive nature makes it helpful for isolating ingredients that don’t play nicely with water. That ability to pick up greasy molecules while leaving water behind saves time and resources. Its relatively high boiling point gives added safety; it won’t flash off the bench or catch fire as easily as lighter alternatives. That said, it comes with its own health and safety baggage. Gloves, goggles, and good ventilation become your best friends when handling it.

Industrial Impact and Responsible Use

All this usefulness doesn’t mean ignoring the impact on health and environment. 1-Chlorohexane, like most chlorinated organics, won’t win any awards for green chemistry. It tends to linger in soil and water, raising red flags about long-term exposure. From my own experience, storage and disposal rules stay strict for good reason. Leaks or accidental spills can lead to contamination, and nobody wants legacy pollution. Companies invest in containment and monitoring, and regular audits help catch problems before they spread.

Looking Ahead: Making Things Safer

Safety and sustainability set the bar for any chemical’s future. Researchers are looking for non-chlorinated alternatives where possible, and tougher regulations keep companies on their toes. For now, 1-Chlorohexane keeps its place in the toolkit—making drugs, supporting discovery, and building new materials. Still, its legacy reminds us to stay careful and inventive, searching for ways to balance industrial progress with a lighter footprint on the planet.

What are the safety precautions when handling 1-Chlorohexane?

Why Respect for Chemicals Protects Everyone

Anyone stepping into a lab learns quickly that some substances demand close attention. 1-Chlorohexane belongs on that list. This colorless liquid has a sweet odor but brings more than just scent to a room. Without healthy caution, its vapors can wipe out focus and even leave a strong headache behind. Accidentally touching or inhaling it ends up being more than an inconvenience—it's a genuine health risk. I remember the sharp sting in my nose once after a careless moment of unscrewing a flask, so now the goggles and gloves stay on, no matter how small the job.

The Basics of Protection

Every chemist has held that familiar pair of nitrile gloves; with a solvent like 1-chlorohexane, standard latex breaks down too quickly. Chemical splash goggles keep fumes away from your eyes and a good lab coat gives one last layer if a spill happens. In my daily lab work, a fume hood isn’t optional when decanting or mixing this liquid. A well-ventilated workspace, paired with a well-maintained hood, will spare your lungs and sense of smell. Chronic headaches for a week taught me that lesson the hard way.

Storage—Where the Trouble Usually Starts

Most serious accidents happen after bottles lose their caps or end up in the wrong spot. I keep 1-chlorohexane away from heat and sunlight, tucked on a lower shelf in a flammables-approved cabinet. Containers labeled with bold, readable tags leave no guessing in an emergency. Lax storage isn't just careless—it gets dangerous as soon as the stuff leaks or boils. Flammable vapors find ignition sources quickly. I saw the aftermath of a lab fire sparked by such a mistake and never forgot that scorched ceiling.

Spills and What Matters in a Crisis

Anyone who has worked with solvents knows spills aren’t a matter of if, but when. Small spills need immediate action—a spill kit with absorbent pads and gloves sits close by. Absorb, bag, and tag before disposing through proper chemical waste routes. Walking away from a small mess to “deal with later” once cost my lab hours of air scrubbing after the fumes spread around the room. For larger spills, evacuation and calling trained response teams keeps a small setback from turning into hospital visits. Sinks, drains, and regular trash cans stay off-limits for chemical cleanup. Even trace amounts can harm aquatic life in the wrong place.

Why Respect Isn’t Just for Work

Repeated exposure can damage the liver and nervous system, and one splash in the eyes may mean a frantic dash to the eyewash station. Building habits—washing hands before lunch, closing bottles tight, checking labels, and double-gloving for long jobs—turns safety from a checklist into a culture. Good habits follow you home, protecting friends and family from cross-contamination on jackets or bags. Clear training for new staff, honest logbooks about incidents, and open conversations make this easier. Ignoring a “small” risk with 1-chlorohexane never saves time in the end. The real win comes from steady respect and simple good habits, each and every day.

What is the molecular formula and structure of 1-Chlorohexane?

The Basics: What Is 1-Chlorohexane?

Chemists and curious minds alike often cross paths with 1-chlorohexane, a molecule that shows up in the lab and industrial settings. It’s an organic compound, specifically an alkyl halide, that swaps a hydrogen atom for a chlorine atom on a straight six-carbon chain. The molecular formula for 1-chlorohexane lands as C6H13Cl, reflecting six carbons, thirteen hydrogens, and one chlorine.

Seeing the Structure in Action

Looking at the skeleton, you get a clear line: CH3–CH2–CH2–CH2–CH2–CH2Cl. The chlorine hangs off the tip of this chain, attached to the first carbon. Sometimes people overlook how that little change—a single chlorine atom at one end—can make a pretty big difference to how this molecule behaves. In practical work, those differences shape the chemical’s reactivity, toxicity, and place in larger syntheses.

Why Does 1-Chlorohexane Matter?

Over time, I’ve seen 1-chlorohexane serve as a building block in the classroom and industry. Early on, I ran experiments with it to learn about nucleophilic substitution reactions. That’s where you realize the chlorine makes the first carbon more attractive for attacks by other molecules. That kind of site on the chain gets a lot more interesting if you want to swap in new groups or start building something more complex.

Outside school benches, makers of agricultural chemicals and specialty polymers keep this compound in rotation. It acts as a key piece to make new molecules, helping to build up chains or tack on chlorine where needed. Labs appreciate how predictably it reacts, taking the guesswork out of synthesis once you understand its setup.

Chemical Safety Warnings from Experience

Handling 1-chlorohexane takes more caution than some textbooks admit. Chlorinated hydrocarbons raise flags for possible impacts on human health. Over the years, my own routine shifted—lab gloves, good ventilation, a respect for skin and lung exposure, plus proper waste disposal. Chlorine’s presence means you get volatility and toxicity that can’t just be washed down a sink. Instead, proper collection and disposal protect not only lab workers, but the waterways and communities around research and industrial sites.

Looking Forward: Smart Handling and Sustainable Practice

The chemistry world keeps evolving, and safety practices improve with better data and tighter standards. Substituting less harmful reagents, if possible, always makes sense. In some cases, you can swap out 1-chlorohexane for cleaner or more biodegradable compounds, depending on the reaction’s needs. Phasing out unnecessary chlorinated substances can shrink a lab or factory’s environmental impact. Staying updated on regulations—and not getting stuck in old habits—protects more than just the current project.

Remember that chemistry, from high school projects to specialized manufacturing, always weaves together knowledge, responsibility, and practicality. Each compound, including 1-chlorohexane, comes with a story of discovery, usefulness, and safe stewardship.

How should 1-Chlorohexane be stored?

Getting Real About Chemical Storage

Years in a chemistry lab taught me that small mistakes create big problems. 1-Chlorohexane isn’t a monster in the bottle, but letting your guard down invites danger. Clear air, dry hands, and a bit of extra caution always work better than fancy alarm systems. Knowing how to hold on to this chemical without trouble matters more than any technical blurb from a safety sheet.

Why Details Matter: What Can Go Wrong

1-Chlorohexane’s vapor might not catch fire as fast as gasoline, but one spark in a cluttered cabinet and the headlines write themselves. Nerve-wracked neighbors and emergency crews keep proof of what happens when someone overlooks the basics. A friend of mine in graduate school got a wicked burn on his arm after combining a loose cap and a curious heat lamp. Accidents don’t warn you—they just happen.

Cool, Dry, and Dark: Not Just a Slogan

Shelving chemicals by the book gets easier after a mishap or two. I keep 1-Chlorohexane far from direct sunlight, tucked in the back corner of a locked cabinet at room temperature. Humidity makes caps swell and labels curl; both signs mean somebody’s going to open the wrong thing or use an old, compromised bottle. Heat will boost pressure inside the bottle or create fumes that escape at the worst possible moment, so avoid warm spots—furnace rooms, busy shelves over radiators, or sunny windowsills.

Glass Before Plastic, Labels Before Mystery

Sturdy glass containers beat plastic for holding up against leaks and tampering. Original factory labels tell you what’s inside, when it arrived, and how long before it’s out of date. I never peel off or scribble over a label—there’s a story behind every code and expiry date. Anything unlabeled goes straight into hazardous waste.

Don’t Mix and Match: Segregation Prevents Chaos

Keeping solvents together and oxidizers at a distance isn’t just tradition. 1-Chlorohexane doesn’t get along with open flames, strong acids, alkalis, or oxidizing agents. Chemicals react in ways most people never see coming, especially on a rushed Friday afternoon. Separate shelves and color-coded bins save more money, time, and nerves than the fanciest spill kit.

Ventilation Is No Luxury

Every storage room I trust runs on a good ventilation system. Inhaling chlorohexane vapors leads to headaches or even affects your liver after enough exposure. Plain fans don’t cut it—dedicated chemical fume extraction pulls vapors away as they build up. Never trust your nose to tell you when the air gets bad; real-time air monitors take the guesswork away.

Training Beats Rules: Keeping People Safe

Everyone who works with chemicals learns more from stories than from pamphlets. Chemical safety classes might take up a Friday afternoon, but good training saves lives and property. Regular drills, a clear spill procedure taped beside every storage locker, and a culture that encourages speaking up about odd smells or leaks keep the workplace in one piece.

Smart Storage Saves More Than Chemicals

The science may look straightforward, but safe storage boils down to consistent habits and treating chemicals with respect. Label everything, keep incompatible items apart, keep good airflow, train every newcomer, and don’t take shortcuts. These aren’t just rules—they’re what kept me and my colleagues healthy and out of trouble for years.

What are the physical and chemical properties of 1-Chlorohexane?

Looking at the Basics

1-Chlorohexane stands out as a fairly straightforward molecule to chemists. It brings together a six-carbon straight chain with a single chlorine atom tacked onto the end. You find it as a colorless, oily liquid. Drag a bottle of 1-chlorohexane into the lab and that sharp, sweet, somewhat chemical smell shows up fast. If you ever worked with chloroalkanes, you’ll find this one familiar — that distinctive aroma goes with the territory.

How It Sits: More Than Just Looks

You’re not mistaking this liquid for water. 1-chlorohexane doesn’t mix with water, keeps a lower density, and floats on top if you ever try that trick. Its boiling point comes in around 135°C, and it freezes somewhere around -70°C. So in a regular lab, you’ll keep it as a liquid with no surprises. Volatility stays moderate, so you’ll catch its scent but don’t expect clouds of vapor unless you really crank the heat.

Digging Into the Chemistry

Like most alkyl chlorides, 1-chlorohexane finds itself pretty handy in organic synthesis. That lone chlorine is no wallflower—it gives the molecule reactivity at that end, opening opportunities for all sorts of substitutions. From personal experience, swapping out the chlorine in SN2 reactions goes faster with smaller chains, but 1-chlorohexane still performs with the right base or nucleophile. The C-Cl bond stands polar, which helps it react, but the six-carbon tail is nonpolar. So it dissolves most easily in other nonpolar or slightly polar solvents like ether or hexane.

Industrial Realities and Laboratory Use

Years working in labs showed me just how picky you need to be with storage. 1-chlorohexane stays stable when you keep it away from light and moisture, but over time and under harsh conditions, it can break down and produce hydrochloric acid. That can cause corrosion in storage if you slack on container checkups.

Out in industry, folks grab 1-chlorohexane mostly for making bigger and fancier molecules. It crops up in pharmaceuticals or as a stepping stone to plasticizers and surfactants. It doesn’t just sit around as a raw chemical. Think of it more as a foundation piece, an ingredient cooks mix into something bigger down the road.

What Raises Eyebrows in Health and Environment

Experience trains you to follow safety sheets closely with substances like this. That oily texture means 1-chlorohexane clings to your skin, and it brings some toxicity if you breathe too much vapor or let it soak in. Direct spills mean quick cleanup and solid ventilation gets top priority, even for folks with iron stomachs.

After years on the job, watching how disposal happens reminds me that many halogenated solvents like this don’t just disappear harmlessly. They can stick around in groundwater and pose health risks. So the best way to keep things green involves careful waste collection, recycling when possible, and opting for less persistent solvents in routine work.

Better Choices Going Forward

A lot of chemists, myself included, have been shifting attention to safer alternatives when possible. Green chemistry pushes mean more people look for ways to swap out chlorinated solvents unless a reaction truly calls for it. Careful design up front, better safety protocols, and rolling out new non-chlorinated methods all take us one step closer to safer labs and cleaner manufacturing.

1-Chlorohexane
1-Chlorohexane
1-Chlorohexane
Names
Preferred IUPAC name 1-Chlorohexane
Other names n-Hexyl chloride
1-Chloro-n-hexane
Hexyl chloride
Pronunciation /ˈklɔː.roʊ.hek.seɪn/
Identifiers
CAS Number 544-10-5
Beilstein Reference 1718735
ChEBI CHEBI:81328
ChEMBL CHEMBL37593
ChemSpider 14201
DrugBank DB08070
ECHA InfoCard 03a7ea4d-c712-4d2f-87d7-67cc0d9ed4f1
EC Number 203-944-9
Gmelin Reference 604758
KEGG C01388
MeSH D002673
PubChem CID 12465
RTECS number MI1575000
UNII 2D8J6H70CT
UN number UN 2376
CompTox Dashboard (EPA) 'DTXSID7020148'
Properties
Chemical formula C6H13Cl
Molar mass 120.63 g/mol
Appearance Colorless liquid
Odor pleasant odor
Density 0.857 g/mL at 25 °C(lit.)
Solubility in water Insoluble
log P 3.5
Vapor pressure 1.87 kPa (at 25 °C)
Acidity (pKa) pKa ≈ 50
Magnetic susceptibility (χ) -6.78e-6 cm³/mol
Refractive index (nD) 1.4190
Viscosity 0.753 cP (20 °C)
Dipole moment 1.89 D
Thermochemistry
Std molar entropy (S⦵298) 221.1 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) -167.9 kJ·mol⁻¹
Std enthalpy of combustion (ΔcH⦵298) -3937.7 kJ/mol
Hazards
GHS labelling GHS02, GHS07
Pictograms GHS02,GHS07
Signal word Warning
Hazard statements H225, H315, H319, H335
Precautionary statements P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P301+P312, P303+P361+P353, P304+P340, P305+P351+P338, P312, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond) 1-1-0
Flash point 61 °C
Autoignition temperature 180 °C
Explosive limits Explosive limits: 1.2–7%
Lethal dose or concentration LD50 oral rat 1620 mg/kg
LD50 (median dose) LD50 (median dose): Rat oral 4,200 mg/kg
NIOSH CNK8000000
PEL (Permissible) PEL (Permissible Exposure Limit) of 1-Chlorohexane: Not established
REL (Recommended) Keep container tightly closed in a dry and well-ventilated place.
IDLH (Immediate danger) 500 ppm
Related compounds
Related compounds 1-Bromohexane
1-Iodohexane
1-Fluorohexane
Hexane