Tributylphosphine didn’t start out as a household name in labs, but its story winds back to the innovative surge of the mid-twentieth century. Chemists saw the need for reliable organophosphorus compounds as research ramped up for catalysts and synthetic agents. By the 1950s, practical methods emerged for synthesizing tributylphosphine, and its use spread from niche academic efforts to large-scale industry. It offered an alternative to triphenylphosphine, trading aromatic bulk for three straight n-butyl groups, which in turn opened new doors for solubility and reactivity. Over the years, it solidified its spot in complex organic transformations, helping engineers build molecules impossible to access before.
Tributylphosphine shows up as a colorless to pale yellow liquid that smells unmistakably pungent, often compared to garlic. Its main feature, though, sits not in its scent, but in the versatility of its phosphorus atom, which acts as a powerful reducing agent and nucleophile in both organic and inorganic chemistry. Retail bottles of tributylphosphine often feature high purity—above 97%—sold for both lab use and industrial production. Its status as a workhorse reagent owes a lot to its adaptability, handling reductions, coupling reactions, and tricky deoxygenations that challenge less robust phosphines.
Tributylphosphine melts just below room temperature, around -80°C, and boils just above 233°C, showing real stability across a wide temperature range. Its density hovers near 0.81 g/cm³ at 25°C, making it less dense than water. This liquid doesn’t dissolve well in water, preferring to mix with common organic solvents like ether, benzene, or chloroform. The phosphorus atom, bobbing at the center, grants nucleophilic character, and the butyl chains allow the molecule to dodge steric blocks in crowded reaction flasks. Exposure to air or sunlight leads to slow oxidation, and that’s a key reason labs keep this compound sealed from oxygen as much as possible.
Suppliers usually send tributylphosphine in amber glass bottles, with labels flagging its flammability and toxicity. Batch certificates note purity, water content, and impurities like tributylamine or trialkylphosphine oxides. Numbers like the CAS: 998-40-3 make tracking inventory simple, but what matters most to chemists is often the actual reactivity in their specific setups. Storage instructions focus on cool, dry, and inert conditions. Chemically resistant gloves, goggles, and fume hoods come standard whenever this liquid comes out, and labs keep detailed Material Safety Data Sheets close at hand.
Synthesizing tributylphosphine usually begins with phosphorus trichloride and butyl magnesium chloride in a dry ether solution. This Grignard route achieves reasonable yields and avoids side products that plagued earlier methods. Some specialty setups use sodium butyl as the alkylating agent, which swaps cost for tighter control over purity. After careful extraction and distillation—all under an inert gas—tributylphosphine comes out ready for filtration and packaging. The whole process rewards careful technique, as even a whiff of moisture or oxygen can spoil the batch by oxidizing the product to its phosphine oxide, which won’t deliver the same punch in downstream reactions.
This compound takes on a host of transformations. In reductions, tributylphosphine can strip oxygen from sulfoxides or clear away azides, regenerating the phosphine oxide byproduct in the process. As a ligand in transition metal catalysis, it supports palladium, platinum, and gold centers, making cross-coupling and cyclization reactions go smoother, more selectively, and with higher yields. The structure of tributylphosphine allows for further tailoring; chemists sometimes modify the alkyl side chains for steric tuning or incorporate it into more complex ligands for research in homogeneous catalysis. Phosphonium derivatives show up in the Wittig reaction, letting scientists build alkenes from carbonyl groups with predictability and finesse.
In catalogs and literature, tributylphosphine pops up with several names, including tri-n-butylphosphine, TBP, or trivalent phosphorous tributyl. It might hide out under local names or company codes depending on the supplier, but the technical community generally recognizes TBP as shorthand. No matter the name, the active phosphine center keeps the function consistent—chemists know what they’re getting when they see any of these labels.
Handling tributylphosphine means treating it with the respect owed to reactive, toxic organophosphorus compounds. Glove boxes and strict ventilation serve as non-negotiable measures, because inhalation or skin contact brings real health risks. Exposure causes irritation, headaches, or, at higher doses, even central nervous system effects. Labs install gas detectors and keep spill kits ready for just such emergencies. Workers need training on emergency procedures, storage, and disposal, since improper cleanup can turn a small leak into a building-wide evacuation. Standard operating protocols stress the need for tightly sealed containers, short exposure times, and double-checks on personal protective equipment.
Tributylphosphine powers a broad swath of chemical innovation. It serves as a ligand in cross-coupling, a field that underpins pharmaceutical development and advanced materials synthesis. Researchers lean on its reducing power to strip oxygen or prepare functionalized molecules that form the backbone of agrochemicals, flavor additives, and polymers. In industry, tributylphosphine catalyzes hydroformylation reactions that pump out aldehydes for further processing. The electronics field handles it for specialty etching and doping during semiconductor manufacturing. Even in fine chemical labs, which push boundaries using small, precisely measured batches, tributylphosphine’s unique reactivity sets it apart.
Tributylphosphine rarely finds itself standing still. Recent efforts focus on greener synthesis routes, aiming for less hazardous precursors or waste byproducts. Catalysis research explores new metal-ligand combinations to save precious metals and boost reaction speed. Computational chemists model the exact electron flow during TBP-assisted reactions, feeding insights back to the bench for smarter process design. Work continues on encapsulated or supported tributylphosphine, hoping to lower the health risks while making it easier to recycle from finished reactions.
The toxic nature of tributylphosphine comes as no surprise, given its reactivity. One of the main concerns centers on respiratory and dermal exposure—rapid absorption leads to both acute and chronic symptoms, and animal testing extends these findings to even subtle neurological effects. Some studies target the breakdown pathways, which often produce trialkylphosphine oxides and, under some conditions, corrosive byproducts with their own health risks. Regulators track workplace air concentrations and set permissible exposure limits, which drives continued investigation into alternatives and engineering controls for high-volume use.
The future for tributylphosphine bends toward safer, more sustainable chemistry. Process intensification—smaller, faster, cleaner reactions—depends on agents like TBP performing at lower concentrations with less waste. New ligand architectures using tributylphosphine form part of the push for greener catalysis, especially as industries look for ways to use less energy and avoid rare or toxic elements. Advances in automation and closed-system handling should further shrink the risks for human workers, allowing TBP’s value to shine in the lab and on the production line. With continuing investment in chemical safety, process innovation, and greener synthetic approaches, tributylphosphine remains a key building block both in labs and industry halls worldwide.
My first time hearing about tributylphosphine came during a college chemistry course. It didn’t sound as familiar as bleach or acetone, but its role behind the scenes stuck with me. This chemical keeps modern manufacturing humming, even if most folks never encounter it directly.
Tributylphosphine shows up in chemical plants where making things efficiently can mean the difference between a profitable product or a wasteful mess. It helps pull off complicated reactions that would stall out or go sideways without some extra help. Its main job? Speeding up chemical reactions as a catalyst, especially when making plastics, pharmaceuticals, and specialty chemicals. Big players in chemistry value it because it helps produce high-purity compounds with fewer unwanted leftovers.
Real advances often come down to how chemists manage to tweak molecules. Tributylphosphine makes itself useful by donating electrons, which can speed up transformations or shuffle atoms into more useful shapes. I remember a professor explaining that, in certain pharmaceutical syntheses, tributylphosphine helps link carbon atoms together in ways nature didn’t plan. Skip this chemical, and you might need more steps, more heat, or risk ruining delicate ingredients.
Its place shines in organic synthesis where it facilitates the so-called Wittig or Mitsunobu reactions. If these sound unfamiliar, think of them as tools for making new drugs or specialty materials—fields where precision means everything. A missed transformation or impure batch can put entire projects out of commission. Tributylphosphine gives scientists a way to build up molecules efficiently and with fewer side-products that could make someone sick or cause long-term problems.
No industrial tool comes without risk. Tributylphosphine releases a stench powerful enough to evacuate a lab in seconds. Worse, it can burn skin or eyes. Its dangers aren’t just about irritation—exposure in higher amounts can lead to nervous system effects. Because of this, anyone using tributylphosphine relies on protective gear, fume hoods, and proper handling procedures. Labs and factories invest in training and strict safety guidelines, since one slip-up can lead to exposure or environmental contamination.
Spills and improper disposal remain a concern. In water, tributylphosphine decomposes, sometimes releasing phosphine gas, which can pose serious risks not only to people but also to aquatic life. Regulatory agencies track and control tributylphosphine transport and storage. These rules aren’t just red tape—they keep workers and communities safer and cut down on legal or cleanup costs later.
Over the last decade, industry and university researchers have searched for safer, greener substitutes. Some labs turn to solid-supported phosphine catalysts or reusable materials which limit direct handling. Others are redesigning key reactions to work with less hazardous reagents. While not every process can ditch tributylphosphine overnight, these innovations push toward cleaner technology. Each improvement means a little less risk to workers and the ground beneath our feet.
Tributylphosphine proves you don’t need a household name to shape vital industries. The chemistry world keeps searching for smarter ways to work, driven by both necessity and a responsibility to people and the planet. My own experience with tricky lab chemicals only sharpened my respect for progress that doesn’t sacrifice safety just to keep factories running smoothly.
I remember the first time I had to work with tributylphosphine in the lab. The supervisor’s talk stuck with me—not just because the chemical could do damage, but also because common-sense steps made a real difference. This phosphorus compound isn’t just a niche reagent for obscure chemistry. It turns up in research, pharmaceuticals, and the odd corner of industrial synthesis. But a bottle of tributylphosphine isn’t something you just leave open on a bench. The stuff smells awful, sure. More than that, it’s toxic and flammable, so working with it means stepping up your habits.
The top danger comes from skin contact, inhalation, or even splashing into your eyes. The phosphorus atom in tributylphosphine makes it reactive—it doesn’t take much to irritate your skin or trigger respiratory issues. I saw a fellow student once ignore a small splash, thinking gloves alone offered total protection. Wrong move. Within minutes, redness and a strange burning sensation set in. That day, we learned that decent gloves (nitrile or neoprene) and even double-gloving for longer work periods are necessary. Lab coats and closed shoes don’t just tick boxes for compliance—they actually prevent pain and trips to the shower room.
One lesson that sticks from working with stinky chemicals like tributylphosphine: never assume basic room airflow cuts it. I’ve watched reactions kept behind fume hood sashes, the operators leaning in just enough to keep control but never risking nose-level exposure. Not just because of the smell—tributylphosphine vapors can irritate mucous membranes, and chronic exposure brings even more risk. Those hoods with steady airflow and prompts warning you to keep that sash down? They actually matter for chemicals like this one. Work outside the hood and you’ll know what you’ve been missing—fast.
Tripping accidents and surprise spills usually have one thing in common: bad planning. With tributylphosphine, you get flammable vapors and a liquid that doesn’t evaporate quietly. I always set up my workspace before opening the bottle, lining up absorbent pads and double-checking glassware. Good habits keep you from scrambling after a spill. Hydrated fire extinguishers and sand for small fires belong just an arm’s reach away. Anything open should get sealed between steps. A tightly closed bottle goes straight back into a flammable storage cabinet—never on open shelves. Darkness and cool temperatures slow decomposition, and no strong oxidizers should share space nearby. Labels matter for quick identification when supervisors do their safety walks or emergencies happen.
Tributylphosphine on the floor isn’t a “just mop it up” situation. I’ve seen routine interrupted for a cheerful yellow absorbent, a mask, and disposable gloves more than once. Small spills disappear into special chemical spill kits; big ones mean evacuating and letting experts handle it. If someone does get a splash, immediate rinsing with water and running to a safety shower makes the difference. Knowing exactly where to find these things saves time that counts when skin is burning or eyes are stinging. Emergency phone numbers should be posted at eye level—hoping you’ll remember them isn’t a strategy.
Getting cavalier around tributylphosphine never works out well. Reading the SDS, updating training, and swapping stories among colleagues builds real-world expertise that beats any memo. Bringing new teammates up to speed shouldn’t get rushed. It’s never just about rules—it’s about walking out healthy and ready for the next day.
Tributylphosphine shows up in chemical discussions with the formula P(C4H9)3. That shorthand stands for one phosphorus atom connected to three butyl groups, each with four carbons and nine hydrogens. Put together, its molecular formula is C12H27P. These numbers don’t just describe what's in a flask—they point to a substance that plays a crucial role in real-world chemistry labs and industries.
Economists and policy makers might glance at these chemical formulas and move on, but tributylphosphine carries real weight for people who work with it hands-on. I used to help out in university labs where organophosphorus compounds sat on open shelves, and you could tell which bottles demanded extra respect. Tributylphosphine falls in that camp.Breathing in a whiff from an opened bottle can ruin your afternoon—pungent, eye-watering, memorable in the worst way. Its smell isn’t just a quirky story. It signals health hazards that lab workers and manufacturers have to mitigate with careful ventilation and training. Safety officers write protocols not to check boxes, but because incidents with tributylphosphine can cause symptoms from headaches to long-term neurological effects.
People know tributylphosphine for its use in organic synthesis and catalysis. It's a strong nucleophile, so it stands out in reactions like the Mitsunobu reaction, which lets chemists swap out those stubborn alcohol functional groups. That opens the door to new pharmaceuticals and specialty compounds that wouldn’t be possible otherwise. The molecule runs like a quiet workhorse in these transformations, helping create building blocks for life-saving medicines, crop chemicals, and smart polymers. Each time a drug company launches a new molecule, it’s likely someone reached for tributylphosphine at some step.
The risk doesn't stop with the user. Tributylphosphine’s volatility means that even with careful handling, fumes can escape and affect both people and the air in the area. I heard stories from colleagues about accidental spills causing whole teams to leave the room for hours. Those experiences stick and remind us that safety in chemistry isn’t about paranoia, but about learned respect.Waste management systems face challenges breaking down organophosphorus waste. Many municipal treatments won’t degrade tributylphosphine effectively, adding pressure on research institutions to set up collection and incineration programs. It’s not just a paperwork problem—it’s about protecting local water and air around production plants and disposal sites.
Chemists now look for alternatives or greener reagents wherever possible. Companies develop new protocols and modify the structure to retain chemical power, but with less impact on health and environment. In my own research days, our team met regularly to swap tips on monitoring for leaks and using the minimum effective dose. Sharing these practices across industries would cut incidents and the load on waste facilities.
Behind the simple formula C12H27P, tributylphosphine demands respect—a reminder that small molecules can shape much bigger stories about innovation, risk, and responsibility.
Tributylphosphine has a knack for causing trouble if it’s left out in the open. Its sharp, garlic-like smell tells you right away that this isn’t the sort of thing you want drifting around a workspace. Even small spills leave behind a persistent odor and can irritate skin, so careless handling turns into a big problem pretty quickly. The chemical’s flammability and tendency to react with air and moisture only add to the headaches. Most people I know in labs have ended up scrubbing benches and bins after one leaky bottle ruins a day. It sits as a reminder: proper storage isn’t optional.
Tributylphosphine reacts fast with oxygen and water. You leave the cap loose or the seal broken, and it forms phosphine oxides—gummy, unpleasant stuff for anyone tasked with cleanup. Resealable, airtight glass bottles with poly-seal caps get the job done. The glass holds up well, and the seals prevent vapors from leaking out. A screw-top flask or a sturdy Schlenk tube does better than cheap plastic, which can let microbes or moisture seep through over time. Many veteran chemists refuse to compromise when it comes to containers, and for good reason.
Warm rooms speed up the breakdown. Even a bright office light can make it degrade faster than people expect. Cold storage below room temperature slows reactions with moisture and oxygen, so refrigerator units set between 2–8°C offer enough chill without turning the chemical into a solid mass. Keeping it protected from sunlight also keeps the sample viable for longer. Labeling the storage space with hazard signs isn’t just protocol—it gives everyone fair warning that even brief exposure could mean an emergency.
Labs without solid venting systems can get overwhelmed with tributylphosphine vapors. Even trace amounts floating around can be a health nuisance. Storing the bottles inside explosion-proof flammable storage cabinets solves two problems at once: fire risk stays low, and fumes stay contained. Cabinets come with built-in ventilation, saving everyone from accidental exposure during routine work. No one wants to find out about poor ventilation because of a surprise fire drill or a visit from the safety inspector.
I spent a summer cleaning up after spills in a small academic lab. One improperly sealed bottle of tributylphosphine didn’t look concerning at first glance. By the following morning, everything from gloves to steel racks needed scrubbing. The odor clung to clothes for days. That incident hammered home a lesson: don’t cut corners on labeling, glove use, or quick cleanup. From that day, I kept extra spill kits handy and checked bottle caps as often as I checked my phone. Live and learn.
Handling things the right way spread through our team through simple habit. We ran regular training sessions on storage protocols—simple reminders worked better than thick binders no one ever opened. We posted step-by-step callouts on the storage cabinets and made sure fresh lab members practiced bottle-sealing drills. Peer reminders, rather than top-down lectures, made those routines stick. It wasn’t about memorizing rules; it became about not wanting to clean up someone else’s mistakes on your weekend. Respect for safe storage grows out of knowing first-hand how unforgiving tributylphosphine can be if you get overconfident or lazy. Prevention beats cleanup every time.
Walk into a chemistry lab or a specialty manufacturing plant, and some shelves show up with names only chemists enjoy. Tributylphosphine is one of those tough-sounding compounds. It plays a role in organic synthesis and some advanced industry work. If someone is making new drugs, special plastics, or even fiddling with fine electronics, tributylphosphine can end up in the mix. Plenty of industries love powerful chemicals for how much they get done in a small dose.
Most of us aren’t keeping bottles of tributylphosphine in our kitchen, and for good reason. Chemists, engineers, even safety inspectors agree: this stuff needs respect. According to the CDC’s NIOSH and the European Chemicals Agency, tributylphosphine isn’t just a tongue-twister. It can irritate skin, eyes, and lungs quickly. Splashing it on bare arms or getting even a whiff in a tight space stings and sometimes feels like stepping into a swarm of hornets.For my own time in a research lab, I remember people prepping tributylphosphine with two pairs of gloves and a fume hood dialed up high for a reason. Mistakes can mean dizziness, nausea, or burning sensations. A colleague once left a flask open, and half the room fled gasping. Some evaluations flag tributylphosphine as very toxic to aquatic life, too. Drains or garbage bins are out of the question—companies have to send it off as hazardous waste.
Nobody wants a chemical burn or a sudden asthma attack at work. Inhaling vapors might lead to headaches or breathing problems, and long-term exposure raises the risk of more serious health damage. Safety sheets mention risks of organ effects after repeated contact. Most schools and research centers only issue access after specific training for a reason.Lots of workplaces rely on eyeballing chemical bottles, and tributylphosphine doesn’t stand out with a bright label or knockout smell. If routines get sloppy or people skip the goggles, trouble comes quickly. Many chemical injuries happen because someone thinks “it won’t happen to me.” I’ve watched teams turn complacent—until a small spill rushes a coworker to the clinic.
Effective safety practices save people from learning the hard way. Always suit up with gloves, lab coat, and solid eye protection. Run the experiment in a good fume hood, away from anyone who isn’t ready for the risks. Storage adds another layer: tributylphosphine can react with oxidizers or acids, so leaving it lying around isn’t smart.Industrial users keep detailed logs and label everything, and in my experience, that saves more than just paperwork headaches. Regular safety drills, up-to-date hazard communication, and a clear system for waste disposal help tamp down on both accidents and environmental damage.
The reach of tributylphosphine isn’t huge for most families, but workers at manufacturing sites, academic labs, or chemical transportation deal with it. Hazards don’t always knock on the front door—they sneak in through everyday routine. That’s why anyone handling tributylphosphine deserves training, gear, and a culture that puts safety above convenience.As chemical technology pushes forward, the demand for careful, informed use of risky tools like tributylphosphine only climbs higher. Tracking health data, sharing real incident stories, and improving access to less hazardous alternatives help protect both workers and neighbors.
| Names | |
| Preferred IUPAC name | Tributylphosphane |
| Other names |
Phosphine, tributyl-
Tributyl phosphorus n-Butylphosphine TBP |
| Pronunciation | /ˌtraɪˌbjuːtɪlˈfɒsfiːn/ |
| Identifiers | |
| CAS Number | 998-40-3 |
| Beilstein Reference | 1718734 |
| ChEBI | CHEBI:35257 |
| ChEMBL | CHEMBL146463 |
| ChemSpider | 50438 |
| DrugBank | DB03714 |
| ECHA InfoCard | 01-2119957839-14-0000 |
| EC Number | 211-735-5 |
| Gmelin Reference | 8788 |
| KEGG | C01781 |
| MeSH | D017929 |
| PubChem CID | 11717 |
| RTECS number | TD3325000 |
| UNII | 484O9045Z2 |
| UN number | UN1993 |
| Properties | |
| Chemical formula | C12H27P |
| Molar mass | 290.43 g/mol |
| Appearance | Colourless to yellow liquid |
| Odor | disagreeable |
| Density | 0.811 g/mL at 25 °C(lit.) |
| Solubility in water | Insoluble |
| log P | 1.63 |
| Vapor pressure | 0.10 mmHg (20 °C) |
| Acidity (pKa) | 8.5 |
| Basicity (pKb) | 3.2 |
| Magnetic susceptibility (χ) | -59.0e-6 cm³/mol |
| Refractive index (nD) | 1.442 |
| Viscosity | 0.824 cP (20 °C) |
| Dipole moment | 3.09 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 445.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -322.6 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -4070 kJ/mol |
| Hazards | |
| GHS labelling | GHS02, GHS06 |
| Pictograms | GHS06,GHS07 |
| Signal word | Danger |
| Hazard statements | H301, H311, H331, H314 |
| Precautionary statements | P210, P261, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312 |
| NFPA 704 (fire diamond) | 2-3-2-W |
| Flash point | 85 °C |
| Autoignition temperature | 225 °C |
| Explosive limits | Lower: 1.1%, Upper: 6.8% |
| Lethal dose or concentration | LD50 oral rat 247 mg/kg |
| LD50 (median dose) | LD50 (median dose): Oral rat LD50 = 247 mg/kg |
| NIOSH | WA6475000 |
| PEL (Permissible) | PEL: Not established |
| REL (Recommended) | 0.1 ppm |
| IDLH (Immediate danger) | 200 mg/m3 |
| Related compounds | |
| Related compounds |
Triphenylphosphine
Trimethylphosphine Triethylphosphine Tri-n-propylphosphine Tri-n-hexylphosphine |
