Phosphonium salts, including tributylhexadecylphosphonium bromide, trace their roots back to research exploring alternatives to more conventional ionic compounds for catalysis and material science. Over the past few decades, the chemical industry shifted its focus to ionic liquids for their ability to dissolve a variety of materials that struggle with traditional solvents. In the late 20th century, scientists got their hands on more reliable methods for synthesizing large phosphonium cations. This led to substitution of bulky alkyl chains, including hexadecyl and tributyl, onto the phosphorus center. As the environmental landscape changed, these compounds came under scrutiny for their handling, utility, and safety, pushing researchers to balance innovation with caution.
Tributylhexadecylphosphonium bromide stands out among phosphonium salts owing to the combination of its long alkyl chain and its tri-n-butyl groups. The molecular structure lends it a special mix of hydrophobic and ionic behavior, giving it uses in phase transfer catalysis and as a component in ionic liquids. In my own time at the bench, the texture of these salts always seemed somewhere between waxy and crystalline, with a kind of oily yet powdery feel, especially at room temperature. This unique physical state drives some labs to select it over quaternary ammonium cousins, since those often end up clumping or caking in less-than-ideal storage.
White, off-white, sometimes taking on a faint yellow tint, tributylhexadecylphosphonium bromide has a hefty molecular weight. The long hydrocarbon tail means it's only slightly soluble in water, but much happier in ethanol and some chlorinated solvents. It holds up under moderate heat, though its thermal stability caps out near the point where decomposition can throw off phosphine and alkyl bromides, and leaving a sticky residue. Some in the field label the density around 1.0–1.1 g/cm³, but the exact number jumps around based on residual moisture and how much it's packed down. It punches in with a melting point above 60°C, which earns it a spot in applications needing a low-melting ionic solid. My own observations, especially in humid summer labs, show it clumps and turns greasy after sitting open, so I always recommend air-tight containers and dry desiccants.
Most suppliers ship tributylhexadecylphosphonium bromide in sealed plastic or glass bottles. Labeling usually shows the molecular formula C28H62BrP, along with purity often above 98%. Handling instructions suggest gloves and goggles, as even small spills can make equipment slippery. The labeling details sometimes include the CAS number (7585-21-1), and the accompanying safety data sheet lays out storage temperature, recommended ventilation, and specific hazard statements. In practical terms, technical specs center on purity, moisture content, and the presence of free hexadecyl bromide, since that impurity tends to crop up without careful washing after synthesis.
Synthesizing tributylhexadecylphosphonium bromide means starting with tributylphosphine and reacting it with 1-bromohexadecane under dry, inert conditions. A straightforward Menshutkin reaction takes shape, substituting the long-chain alkyl bromide onto the phosphorus. Heat gently, about 60–70°C, and a thick oil separates, then solidifies on cooling. Wash the crude product with cold ether or hexane to pull off unreacted starting material. In my hands, yields remain high when minimizing exposure to air and moisture, since both degrade the phosphine reactant. Some chemists try automating this step, but for sensitive use in ionic liquids, I prefer a small-batch approach with TLC to keep reactive byproducts out of the final jar.
Tributylhexadecylphosphonium bromide reacts as a stable salt under standard conditions, but its value rises in quaternization, anion exchange, and phase-transfer catalysis. Swap the bromide counterion for a range of anions—like chloride, tetrafluoroborate, or bis(trifluoromethylsulfonyl)imide—using metathesis in water or alcohol. This opens doors to making custom ionic liquids with different melting points or solvent properties. It stands up well in most organic reactions, but breaks down in the presence of strong bases, releasing tributylphosphine oxide or fragmenting the alkyl chain. Trying to further alkylate the phosphonium center isn’t practical, but the bromide can exchange with nucleophiles in processes like SN2 catalysis, expanding its use in synthetic organic chemistry. During my own attempts at swapping the counterion, patience and thorough washing made the difference—the product turns sticky with leftover acid if rushed.
Look around and you’ll see tributylhexadecylphosphonium bromide also called Hexadecyltributylphosphonium Bromide, or just shorthand THTPB. Chemical catalogs sometimes refer to it by its systematic name, but in most research circles, people drop to initials or “hexadecyl phosphonium salt” for quick reference. Commercial sources slap on product numbers, but unless you’re tracking quality control, the shorthand suffices. This spread of names means double-checking paperwork, especially when ordering or reviewing old research, since “tributyl” and “hexadecyl” sometimes get swapped by mistake in databases.
Handling any phosphonium salt, tributylhexadecylphosphonium bromide included, means respecting the possibility of respiratory and skin exposure. I’ve had colleagues describe mild skin irritation after accidental contact, and nobody appreciates a slippery floor from a spill. Ventilation matters, especially when heating or carrying out large-scale synthesis—trace quantities of liberated alkyl bromides aren’t pleasant. Most labs keep it tightly closed and stored away from bases and oxidizers. Disposal falls under halogenated organics, so the waste stream must meet local chemical management rules. At home in the lab, I make it a point not to store open bottles near acids, since over time even these subtle vapors degrade the salt.
Industries and academic labs use tributylhexadecylphosphonium bromide mostly for phase transfer catalysis, ionic liquid synthesis, antistatic coatings, and as a stabilizer during complex organometallic reactions. The long carbon tail provides amphiphilic properties, which help shuttle ions across interfaces in biphasic reactions. In my experience, a little goes a long way when boosting the efficiency of reactions that struggle with mixing hydrophilic and hydrophobic phases. Some researchers have tried to introduce it as an antimicrobial additive in plastics, banking on the surface-active cation, but scaling remains tricky due to both cost and toxicity concerns. Despite these hurdles, the compound shows up in patent literature for battery electrolytes and specialty solvent blends, earning a spot beyond just classic synthesis.
Ongoing research focuses on pushing tributylhexadecylphosphonium bromide beyond niche uses, inspired by the successes of other ionic liquids in fields like green chemistry and electrochemistry. Green solvent research now looks into replacing classic organic solvents with ionic liquids formed from phosphonium salts for better environmental footprints. I've seen consortia form to optimize recovery from chemical processes and recycle these salts, since their price points rise whenever raw alkyl bromides spike. Projects unfold in both academia and industry, targeting less hazardous derivatives, more versatile anion-swapping protocols, and improved recyclability.
Safety data for tributylhexadecylphosphonium bromide emerges slowly, pieced together from animal studies and in vitro assays. The cation itself can have low acute toxicity, but the long alkyl chain heightens the compound’s tendency to bioaccumulate and provoke cell membrane disruption. Published studies link high concentrations to mild irritation and delayed toxicity in aquatic organisms. These concerns push some companies to restrict its use, or seek out shorter-chain or biodegradable analogues. Personally, the push for transparency in safety data registers with me, as most new chemicals land in the market faster than long-term impacts get published. This lag urges continued monitoring of environmental release and occupational exposure, so labs and manufacturers remain proactive with ventilation, containment, and personal protection.
Future developments for tributylhexadecylphosphonium bromide depend on a combination of finding safer substitutes, designing recycling strategies, and expanding its use in high-value applications that justify the cost and oversight. Research teams gear up for the challenge of integrating renewable feedstocks and refining scalable production. Real breakthroughs could mean swapping out hazardous solvents in battery manufacturing or pharmaceuticals, where toxicity and sustainability drive decision-making. Having worked at the crossroads of chemical manufacturing and green chemistry initiatives, I believe only a collaborative push—linking industry, academia, and regulators—will secure new life for compounds like these, balancing innovation with responsibility to health and the environment.
Tributylhexadecylphosphonium bromide sounds like a mouthful, but this compound shows up in some pretty direct and useful ways. As a phosphonium salt, its structure offers distinct traits that catch the eye of chemists. Its bulky organic tail and unique charge allow it to step into roles where more familiar compounds don’t quite deliver.
One central application sits in the world of synthesis. This salt acts as a phase transfer catalyst. Chemists face a stubborn problem: getting ingredients to react when they hang out in separate liquid phases, like oil and water. This compound bridges the gap, pushing reactants across those lines and speeding up essential processes. In my experience studying industrial purification, cutting down the number of steps means cleaner products and less waste. The right catalyst saves energy and helps factories meet tighter emissions rules.
Phase transfer catalysis isn’t just chemistry on paper; it shapes how large-scale manufacturing works. Bromine and phosphorus might sound intimidating, but they sit right at the crossroads where efficiency and practical production meet. Factories using these compounds can process pharmaceuticals, plastics, and specialty chemicals at lower temperatures and pressures, shrinking costs. Peer-reviewed studies show that these salts often work where older catalysts stall, bringing stubborn reactants together. That ability matters to anyone who cares about sustainable manufacturing and cleaner chemistry.
Over the past few years, demand for antimicrobial substances has risen fast. Offices, schools, and hospitals turn to treatments that keep surfaces safer. Research shows phosphonium-based compounds, including tributylhexadecylphosphonium bromide, push back hard against bacteria and fungi. Their structure lets them slip through microbial membranes, disrupting life processes and reducing infection risks. As someone who’s followed infection control protocols in healthcare settings, I’ve seen firsthand how better antimicrobials mean fewer sick days and less spread in public spaces.
These salts go beyond just laboratory settings. They work as active ingredients in coatings for medical devices, food packaging, and water filtration systems. The science backs up their safety and impact when used responsibly. Still, using them on a large scale requires constant monitoring; organisms adapt quickly. Companies and public health authorities need to track effectiveness in real time and invest in alternating treatments to fight resistance.
Many people don’t realize solvent choices matter just as much as the chemicals themselves. Some solvents pose hazards to workers and the environment. Tributylhexadecylphosphonium bromide forms ionic liquids—salt-like materials that remain liquid around room temperature. These new liquids offer a safer, less volatile option for running tough reactions. They not only avoid the harsh smell of classic solvents but also provide unique properties, like better conductivity and tailored solubility. Research from the last decade shows their potential in green chemistry initiatives. I’ve spoken with academic researchers trying to replace traditional solvents, and they consistently highlight these phosphonium salts as a go-to.
The promise of tributylhexadecylphosphonium bromide goes far beyond the lab bench. Catalysis, antimicrobial action, and the birth of safer solvents push innovation in real-life industries. Companies should keep investing in toxicity testing and seek sustainable sources, since public trust relies on both performance and safety. By taking lessons from both chemistry and direct experience, it’s clear these compounds hold power to clean up, simplify, and improve modern manufacturing and health protection—provided we stay mindful and responsible with their adoption.
People who handle chemicals like tributylhexadecylphosphonium bromide at work or in the lab know that where and how you store something shapes its shelf life, its reliability, and the safety of everyone nearby. This compound, used in applications ranging from catalysis to ionic liquids, carries certain quirks thanks to its phosphorus-based structure combined with bulky organic groups. Based on what researchers and chemical suppliers recommend, and my own experience managing a small-scale lab, some common-sense steps help keep this material stable and limit risk.
Tributylhexadecylphosphonium bromide absorbs moisture from the air. Water in your storage area ruins batches and leads to unexpected side reactions. Storing it in airtight containers makes a difference, preferably in materials that block moisture—think amber glass or high-grade plastic. Open containers mean humidity creeping in, so sealing between every use becomes routine. The compound doesn’t thrive under humid conditions, so storing it in a cool, dry spot out of direct sunlight matters. Products like silica gel packets, dropped into your storage drawer, can help soak up stray moisture and keep the contents dry.
Most labs agree on cool storage for their sensitive chemicals. High heat breaks down organic phosphonium salts or encourages clumping and discoloration. Keeping tributylhexadecylphosphonium bromide at around 2-8°C—straight from the chemical suppliers’ own guidelines—extends its lifespan and ensures consistency. A standard laboratory refrigerator, separate from food, works well. Don’t freeze it, though. Freezing sometimes encourages condensation inside the packaging when it warms up again.
Any strong acid or oxidizer sitting nearby ramps up the risk, so I recommend storing this compound separately. Accidental splashing or vapor mixing in tight spaces can trigger unwanted chemical reactions. Shelving tributylhexadecylphosphonium bromide far from incompatibles like strong bases or oxidizers just makes sense, even if your space gets cramped.
Inconsistent storage increases the hazard rating during daily handling. Environmental Health and Safety guidelines flag organophosphorus compounds for potential skin or eye irritation and toxicity. I keep a spill kit within reach: gloves, goggles, and a small mask. Ventilated spaces reduce risk even further when pulling samples or repackaging. These steps also support lab colleagues and custodians coming into the space later on.
Accurate, legible labels pay off months later. Dates, lot numbers, and supplier details printed directly on every container cut down on confusion and minimize accidental mixing. Lab notebooks or simple spreadsheet logs—something many seasoned chemists already do—can help you track aging inventory, focus on first-in, first-out usage, and spot when a replacement order makes sense.
Many workplace accidents come down to shortcuts or unclear instructions. Manufacturer safety sheets lay out most of what you need, but on-the-ground reminders and regular reviews build good habits. I like to review storage policies every few months and share observations with coworkers—even five minutes at a regular meeting can curb future mistakes. Building a culture of careful handling means fewer spills, less product waste, and everybody heading home healthy at the end of the day.
Tributylhexadecylphosphonium bromide shows up in labs and in industrial processes, especially in chemistry experiments focused on ionic liquids and catalysts. Not many folks outside specialty fields have heard about it. The challenge with chemicals like this one—long, intimidating names aside—is that their risks often get overlooked or misunderstood amid all the complex jargon. Yet, questions about health and the environment need clear and honest answers.
A lot of chemicals deserve a closer look for side effects or risks. Tributylhexadecylphosphonium bromide belongs to the class of phosphonium salts. Experts know that some salts in this family act as skin or eye irritants, and many can harm aquatic life if spills head down the drain. Toxicity studies on this specific bromide sit in short supply, but its structural relatives show patterns of danger when inhaled, swallowed, or handled carelessly. Workers who spend time with the powder or its solutions sometimes report itching, coughing, or eye discomfort. Severe reactions happen with high exposure or in settings without proper safety steps—no open wounds and bare hands around these chemicals.
Looking at lab data, researchers have flagged medium-range toxicity in animal studies. In aquatic environments, the chemical might trigger problems thanks to slow breakdown of the molecule—fish and small water critters can die or show slow growth after exposure. Regulators say that these salts need careful waste management. Leaving it unaddressed can turn small spills into sources of pollution, especially because marine and river life can’t clear these substances out easily.
Big labs already build special cabinets and tanks for handling and storing this class of chemicals. People using them wear gloves, goggles, and sometimes respirators. Safety data sheets from leading suppliers warn about strong reactions with oxidizers, the danger of fire, and severe skin or eye irritation. My own experience in an academic lab—filling out chemical inventory sheets and triple-checking bottle labels—says nobody wants to clean up after a careless chemical handler. You feel it in your throat or nose if safety gear slips. Even though not as notorious as older industrial toxins, all it takes is a splash without protection, and suddenly you’re heading to the emergency shower.
Dealing with waste also brings headaches. Direct disposal in drains or the natural environment isn’t just lazy, it’s illegal in most countries. The right way means labeled, sealed containers and a hazardous waste pickup. Colleagues who’ve ignored these rules often learned hard lessons—accidents spark investigations and sometimes fines. For small companies or research labs, skipping these steps can wreck budgets and reputations.
Switching out dangerous compounds with safer ones stands as a real solution for many labs. Training for everyone who touches specialized chemicals makes a difference, too: you don’t have to be a chemist to check glove compatibility or spot chemical fume hoods. Following published regulatory guidance—like OSHA’s standards and international transportation rules—keeps both people and the environment safer. If supply chains start offering more rigorous toxicity data, buyers and users can choose with clear eyes.
Chemicals don’t care about ignorance. Anyone using tributylhexadecylphosphonium bromide must respect the hazards, learn the safety steps, and keep both health and local ecosystems in mind. That attitude protects more than just the workers in lab coats.
Tributylhexadecylphosphonium bromide is a mouthful to say, but it stands out in the world of organophosphorus chemicals. Its formula is C28H62BrP. This formula looks intimidating at first glance, but breaking it down gives a clearer idea of what’s going on inside one molecule. The compound carries a phosphonium core with three butyl groups and one big hexadecyl chain attached to it, which reveals why it has such a long name. The structure forms a salt with a bromide ion balancing out the positive charge of the phosphonium ion.
The molecular weight clocks in at about 525.66 g/mol. That number comes from the combined atomic masses—carbon with 28 atoms, hydrogen with 62, a single phosphorus, a bromine, and balancing out the arithmetic. This heavy hitter doesn’t just make a statement on paper. It shows up in practical uses, especially in the business of ionic liquids and specialty surfactants. Labs take advantage of the strong ionic interactions and the notable hydrophobic tail, which make this compound useful for extraction processes and certain catalysis pathways.
Formulas and weights are not just trivia for a chemistry exam. If someone misplaces a hydrogen or counts a carbon twice, synthesis can fail. Material safety data, regulatory submissions, and purchasing all depend on the numbers being right. Imagine ordering a batch for a research project, only to realize the supplier works from incorrect data. Wasted resources, money, and time. Errors like this frustrate researchers and slow innovation. I’ve been there, poring over paperwork to double-check every line because a typo crept into an early version of a lab report. Trust falls apart quickly in science when numbers get fuzzy.
Phosphonium salts carry with them the responsibility of safe handling. High molecular weight and hydrophobicity often mean the compound won’t dissolve well in water. Spills stick around longer, environmental toxicity stretches further than many realize. Responsible users always read safety data sheets, store the material in sealed containers, and avoid letting it slip out into wastewater. Local regulations in some places now demand clear records of every gram, so there’s a growing burden of traceability, too. If you use it in the lab, gloves and proper ventilation aren’t optional—they’re a must.
Mistakes in calculation turn up most often in multi-step syntheses or scale-up procedures. Experienced chemists check formulas, not just on bottle labels but against published databases, peer-reviewed journals, and supplier certificates of analysis. Balancing vigilance and efficiency remains key. Once, a mistake in a reagent’s reported purity cost a colleague a full week of work—an expensive lesson in why double-checking isn’t just for rookies. Teaching new researchers to build this habit early makes life easier for everyone. Honestly, these small steps in the lab echo through every future project relying on those foundational materials.
As chemistry evolves, big molecules like tributylhexadecylphosphonium bromide find new markets in green chemistry, solvent extraction, and phase transfer catalysis. Accurate data guides responsible innovation. Industry and academia both share in that duty. Small changes on paper can cascade through a project—so every number, every formula, every gram really does matter.
I’ve spent long hours in labs, and I know shortcuts in chemical handling can cost a lot. Tributylhexadecylphosphonium bromide doesn’t belong in the “harmless” camp. Studies highlight skin and respiratory irritation, plus it can cause trouble for aquatic life. Take this clear: gloves, goggles, and a good fume hood aren’t upgrades—they form the basics. Grab those nitrile gloves, put on a lab coat, and double-check the fit of your safety glasses. Splashing this stuff on your skin isn’t an abstract hazard, it’s an instant regret.
Cramming bottles onto any old shelf could ruin your day. Dry, cool, and well-marked storerooms keep accidents away. Avoid sunlight and big temperature swings, both speed up chemical changes—and nobody enjoys surprise fumes leaking from a supposedly sealed flask. I once saw a bottle left uncapped in a sunny spot; ten minutes later, the room reeked and everyone scrambled. Simple mistakes like that are easy to avoid.
Every lab hand learns at least one lesson the hard way. A tumble off the bench turns into a big problem fast. Spill kits aren’t decorations. Absorbent pads, neutralizing agents, and heavy-duty bags should sit where you can reach them with your eyes closed. Pick up solids slowly and sweep them into a sealable bag. Damp areas? Blot—don’t rub. Contaminated surfaces need a full cleaning with detergent and copious water. Treat every mess like it’s more dangerous than it looks.
Drains aren’t magical; flushing phosphonium compounds straight into the water supply grabs attention from regulators for good reason. Environment agencies classify these substances as hazardous waste. In my work, nothing leaves the bench unless a label sticks to its case, detailing contents. Partnering with licensed hazardous waste firms may not thrill your finance department, but fines and environmental damage punch harder. Check the latest EPA rules or your local government’s guidelines, since they keep getting stricter for persistent pollutants like this.
Posters on the wall do less than a five-minute conversation with a tech who’s handled the material for years. I remember learning from one mentor who pointed out every shortcut he’d seen end in trouble. Fresh hires need the same coaching. Go beyond online modules—walk new team members through the storeroom and practice a fake spill. Hands-on run-throughs build confidence. Labs that brag about never having incidents often have morning huddles, equipment checks, and wrap-up reviews baked into the routine.
Accountability keeps everyone alert. Leaving a mess on your bench isn’t a private problem; it endangers the whole team. Stressing over labels and logs might feel tedious, but over time, diligence beats luck. Think of the stories—accidents aren’t rare, and tragedies almost always started small. Real stewardship comes from every worker refusing to make exceptions “just this once.” That’s how companies avoid disaster headlines and workers get home safe.
| Names | |
| Preferred IUPAC name | hexadecyltributylphosphanium bromide |
| Other names |
Hexadecyltributylphosphonium bromide
TBPHD Br |
| Pronunciation | /ˌtraɪ.bjuː.tɪlˌhɛk.səˈdɛs.ɪlˌfɒsˈfoʊ.ni.əm ˈbroʊ.maɪd/ |
| Identifiers | |
| CAS Number | 148680-55-3 |
| Beilstein Reference | 1951146 |
| ChEBI | CHEBI:72858 |
| ChEMBL | CHEMBL1907853 |
| ChemSpider | 22699203 |
| DrugBank | DB11104 |
| ECHA InfoCard | 100.143.419 |
| EC Number | 612-021-5 |
| Gmelin Reference | 1261114 |
| KEGG | C21112 |
| MeSH | D037191 |
| PubChem CID | 11482240 |
| RTECS number | TC6300000 |
| UNII | IK3D09IU62 |
| UN number | UN3077 |
| CompTox Dashboard (EPA) | DTXSID3020487 |
| Properties | |
| Chemical formula | C28H62BrP |
| Molar mass | 549.6 g/mol |
| Appearance | White to off-white solid |
| Odor | Odorless |
| Density | 1.05 g/cm³ |
| Solubility in water | Soluble in water |
| log P | 1.51 |
| Vapor pressure | 0.0 mmHg at 25 °C |
| Basicity (pKb) | 15.0 |
| Magnetic susceptibility (χ) | -77.5×10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.485 |
| Viscosity | Viscosity: 134 cP (25 °C) |
| Dipole moment | 6.94 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 303.6 J·mol⁻¹·K⁻¹ |
| Hazards | |
| Main hazards | Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. Toxic to aquatic life with long lasting effects. |
| GHS labelling | GHS07, GHS09 |
| Pictograms | GHS05,GHS07 |
| Signal word | Warning |
| Hazard statements | H302, H315, H319, H335 |
| Precautionary statements | P264, P280, P305+P351+P338, P337+P313 |
| Flash point | > 190 °C |
| Lethal dose or concentration | LD50 Oral Rat 128 mg/kg |
| LD50 (median dose) | LD50 (median dose): 500 mg/kg (Rat, Oral) |
| NIOSH | VY8750000 |
| PEL (Permissible) | PEL (Permissible Exposure Limit) for Tributylhexadecylphosphonium Bromide: Not established |
| Related compounds | |
| Related compounds |
Tetrabutylphosphonium Bromide
Tributylmethylphosphonium Bromide Tributyloctylphosphonium Bromide Trihexyltetradecylphosphonium Bromide Tetrabutylammonium Bromide |
