Chemists first turned to tributylphosphine oxide during the rapid expansion of organophosphorus compounds in the wake of World War II. The field caught fire once the value of organophosphines became clear, both in therapeutics and catalysis. Early on, tributylphosphine staked out its place in the synthesis labs that wanted a safer, more accessible phosphorus reagent. Phosphorus chemistry used to carry a heavy reputation for fire risks and toxic vapors, but tributylphosphine oxide helped shift the narrative toward safer and more versatile options. Researchers spent years tweaking reaction conditions and purification techniques. Improvements didn’t come overnight, but by the 1960s, straightforward syntheses and reliable analytical methods had demystified much about the compound.
Tributylphosphine oxide isn’t flashy. It does exactly what is expected from an organophosphine oxide, but with a set of features that often make it the default pick in academic projects. Its commercial product is a colorless to pale yellow liquid, generally stable and easy to measure. You'll often see it supplied in glass bottles, tight-sealed due to its modest but noticeable odor, and bearing all relevant safety hazard symbols required by global transport agencies. Any chemist who has worked in organophosphorus chemistry probably kept a bottle handy, whether for catalysis or as a byproduct ready for extraction and disposal.
What catches the eye first is the moderate boiling range, typically near 360 °C, and a melting point resting far below room temperature. With a density hovering around 0.97 g/cm³, it pours out as an oily liquid. Its solubility defines its lab applications: insoluble in water, but mixes well with common organic solvents like ether and benzene. This makes it a favorite in extractions where water compatibility would only complicate things. Its molecular weight clocks in at about 266.37 g/mol. As for structure, the P=O bond brings significant stability, holding up in both air and under typical lab lighting, reducing worries about rapid degradation or handling troubles.
Suppliers tend to provide tributylphosphine oxide with purities from 95% to ultra-pure grades above 99%. Labels cite not just its chemical name but also synonyms, CAS number (such as 997-80-4), and hazard ratings like “Irritant.” Each shipment must display GHS labeling. SDS sheets provided by reputable vendors walk buyers through spill response, fire-fighting guidance, and PPE requirements. Lab-grade packaging is often double-sealed. Certificates of analysis typically detail appearance, purity (by NMR or GC), and residual solvent levels.
Synthesis most often involves slow oxidation of tributylphosphine, typically using hydrogen peroxide or molecular oxygen as the oxidant. Hydrogen peroxide in an alcohol or water solution gets the job done efficiently in most small-scale preparations, avoiding harsh side-products and yielding high-purity results. In larger chemical plants, liquid-phase oxidation takes place under cooled and well-ventilated setups, prioritizing containment and control of exotherms. Careful removal of excess hydrogen peroxide and thorough washing of the product ensure high yield and minimum contamination, cutting reprocessing times and reducing costs.
Tributylphosphine oxide shows up both as an end product and as an intermediate. The strong P=O bond prevents easy reduction, but chemists learned to harness this stability in practice. It acts as a ligand for certain transition metals, supports organocatalytic cycles, and can be recycled or modified in situ under laboratory conditions. Researchers sometimes aim to functionalize the butyl side chains for downstream transformation, but its greatest role still lies in tolerant, controlled reaction environments, especially in Wittig or related syntheses, where the oxide emerges as a predictable and removable byproduct.
Various synonyms turn up, including TBPO and tributylphosphine oxide—sometimes spelled with spaces, other times condensed into one word. Some catalogues use alternative names like tri-n-butylphosphine oxide or P,P-dibutylphosphinoxyl. Although names differ, they refer to the same core molecule. Chemical suppliers reference CAS 997-80-4 consistently. Ensuring clarity in labeling avoids confusion in the lab and in shipping paperwork, cutting out errors that waste both time and money.
Working with tributylphosphine oxide means paying attention to skin contact and inhalation routes. Globally-recognized safety agencies rate it as an irritant, not an outright toxin, so basic lab gloves and goggles offer essential protection. Standard fume hoods keep vapors out of breathing range, and good housekeeping prevents contact with food or drink. Spill kits and absorbent materials should be stored close to workspaces. Safety protocols align with good laboratory practice—no need for custom containment or extreme PPE in most settings, but vigilance on exposure always pays off long-term.
Chemists reach for tributylphosphine oxide during organophosphorus transformations, particularly as a phase-transfer agent and as a byproduct in Wittig-type reactions and Staudinger reductions. Some industries use it as a specialty solvent for extracting rare earth metals or for modifying catalyst behavior in polymerization setups. In the pharmaceutical world, it streamlines workflows by shortening separation steps, since it dissolves in organics but not in water. Environmental analysis labs sometimes draw on its extractive qualities to trace heavy metals, especially as regulatory standards on trace contaminants grow tighter each year.
Academic circles keep pushing the limits of what tributylphosphine oxide can achieve, often by examining its lesser-known properties. Research continues around its role in metal complexation, seeking out new ligands that deliver both selectivity and stability for high-value catalysis. Some university labs chase green chemistry goals, testing recyclable systems where tributylphosphine oxide plays a part in closed-loop syntheses. Philanthropic funds sometimes back toxicology studies, especially where tributylphosphine derivatives cross over into medical or agricultural treatments. Collaboration with industry partners speeds up the journey from journal article to scaled-up batch.
Long-term toxicology studies point to relatively low acute hazard but flag mild irritation to skin, eyes, and respiratory passages. Chronic exposure studies remain ongoing—there’s always talk about potential for bioaccumulation, but hard data still appears limited. Industrial hygiene experts recommend routine air monitoring in workplaces with high throughput. Waste handling follows state and national legislation, requiring collection and incineration under controlled conditions. Advances in personal protective technology, along with automation in liquid handling, further limit occupational exposure risks. Scientists expect new data within a few years as part of large, multi-center studies that combine animal data with epidemiological reviews.
Chemistry trends point toward expanded use for tributylphosphine oxide. Catalysis remains the big draw, especially with industry shifting toward greener, more atom-efficient syntheses. As regulators clamp down on hazardous waste, demand for more selective, recyclable phosphorus ligands keeps rising. Market analysts expect applications to broaden—in energy storage, environmental analysis, and possibly materials science, where organophosphorus frameworks play into new battery chemistries and nanocomposites. Ongoing R&D examines tweaks to the molecule for even better selectivity, pairing, and reactivity, with patent applications on both the academic and start-up sides hinting at a bright commercial runway.
Walk into a laboratory where new medicines take shape or where electronics keep getting smaller and faster, and you're likely to stumble upon tributylphosphine oxide. Its name doesn't pop up on product labels at the drugstore, but over many years in science writing and close work with chemists, I've seen how this clear, oily substance keeps projects moving in drug discovery, material science, and chemical engineering.
Pharma firms put tributylphosphine oxide to work. In the world of organic synthesis, making a target molecule can stretch out over dozens of steps. Each step risks leaving behind chemical byproducts—little bits that might block the next stage or muddy the final product. Tributylphosphine oxide helps tidy up these messy leftovers. For instance, in the famous Wittig reaction, it crops up as a byproduct, helping drive the reaction toward making double carbon bonds, a core part of building drug molecules. This part gets overlooked outside labs, but without these efficient clean-up molecules, costs and timelines could spiral out of control. Getting a new treatment to patients depends on keeping those steps sharp and reliable, reducing waste every time.
Electronics companies look for ways to improve chip speed and reliability. Tributylphosphine oxide finds a home here too. Engineers coat microchips with ultra-thin films to protect them or tweak how electricity flows. These films often need precursors that behave predictably at high temperature or under vacuum. Tributylphosphine oxide can serve as a ligand, partnering up with metals to deposit nanometer-thick layers inside a chip’s maze of tunnels. Back in grad school, I saw how tiny shifts in what precursors you picked affected whether a batch of chips passed tests. Engineers prefer substances that keep their cool under tough conditions, without leaving gunk behind. This phosphine oxide does just that.
Chemists keep looking for ways to clean up after themselves. Before green chemistry took off, waste streams coming out of plants could end up laced with toxins. Tributylphosphine oxide isn't perfect—it still demands careful handling—but compared to heavy metals or hard-to-break organics, it makes processing simpler. I once toured a plant retrofitted to recover solvents and minimize troublesome byproducts. The operators gravitated toward solutions that kept their clean-up routines straightforward. Tributylphosphine oxide, stable under air and moisture, lets those teams avoid complicated containment or huge expenses in neutralization. That stability becomes a real asset throughout industry.
Nothing comes free. Occasional supply hiccups for tributylphosphine oxide ripple through labs and factories. If suppliers run short, certain reactions grind to a halt. Researchers have tried swapping in other phosphine oxides, but not every swaplike for like—properties change, yields drop, procedures have to be tuned for weeks. Teams now hunt down greener alternatives or design systems that produce less waste upstream, and companies track raw material sourcing just to head off surprise shortages. Looking at life-cycle assessments could help nudge industrial users to think ahead about what happens to every kilo shipped in and out. Public databases, open-source research, and government incentives could open more doors for molecule recycling and tamer alternatives.
In the end, tributylphosphine oxide keeps a low profile but a wide impact. Safer handling, smarter substitution, and more openness in supply chains offer routes forward. As new industries pop up and existing ones tighten their environmental rules, deeper understanding and collaboration round out the picture, keeping complex chemistry balanced with real-world needs.
Many chemicals sound like a mouthful, and tributylphosphine oxide doesn’t roll off the tongue for most people. Those of us who have done time in academic or industrial labs recognize the importance of asking basic questions about substances before handling them. Tributylphosphine oxide looks pretty mild at first glance: it’s a colorless to pale yellow liquid, it doesn’t reek like sulfur compounds, and it doesn’t set off the Geiger counter. But is it safe to work with, especially if you aren't a seasoned chemist?
Digging into safety data, tributylphosphine oxide falls under a category some would call “not especially dangerous.” That is not the same as harmless. A chemical like this still demands respect. The National Institute for Occupational Safety and Health (NIOSH) and other government organizations do not list it as one of the most worrisome substances, but toxicity studies in rodents show that large doses can cause harm. Studies found that if it’s ingested in significant amounts, animals may experience toxic symptoms: lethargy, tremors, and weight loss after repeated exposure. Skin and eye irritation are possible if you handle it without gloves or splash it during transfer.
Occupational exposure limits for tributylphosphine oxide haven't been set, probably because regular folks rarely use it outside advanced chemistry labs. If someone breathes in its mist or accidentally gets it into the eyes, first aid guidelines match those for modestly hazardous organic chemicals: rinse well with water, move to fresh air, and seek medical attention for symptoms that don’t clear up quickly.
Tributylphosphine oxide isn’t meant for the wastebasket or sink. Even though its acute toxicity registers as moderate compared to more notorious lab chemicals like phenol or cyanide, careless disposal still presents a risk. Most chemistry facilities treat it as chemical waste, shipping used materials to licensed handlers. The reason is simple: any compound that sticks around in soil and water—with the ability to enter biological systems—warrants caution. Although tributylphosphine oxide doesn’t persist quite like PCBs or heavy metals, research suggests it can cause trouble in aquatic environments if dumped without controls.
Incidents in the past—like labs suffering fire hazards because of chemical collection mistakes—underline why it pays to follow best practices, even for relatively “mild” organophosphorus compounds. Phosphorus-containing substances sometimes break down into more hazardous materials, especially when exposed to high heat or strong acids.
Schools, research labs, and manufacturers all benefit from a culture that recognizes both big and small chemical hazards. Training shouldn’t skip over chemicals like tributylphosphine oxide just because they lack a skull-and-crossbones label. Workers deserve clear advice: wear gloves and goggles, work with good airflow, and keep containers tightly closed after use. Regular safety audits catch practices that slip over time; this vigilance reduces chances of chronic exposure or sudden accidents.
It helps when workplaces post clear instructions for chemical handling and disposal near storage shelves. Anyone in charge needs to update inventories so materials that degrade or change containers over time don’t become future hazards. Solutions like these let both newcomers and pros stay healthy, so the talent pipeline in science and tech doesn’t shrink from needless chemical injuries.
Respecting tributylphosphine oxide—just as you would any unfamiliar chemical—keeps accidents rare and lets labs run without drama.
Tributylphosphine oxide goes by the formula C12H27OP. This means its molecule is made up of twelve carbon atoms, twenty-seven hydrogen atoms, one oxygen atom, and one phosphorus atom. The structure might not look like much on paper, but it tells an honest story about the way science and industry use this compound. I remember in a college chemistry lab, it wasn’t always the new flashy molecules that did the heavy lifting — often, simple, practical structures like this made a world of difference in tests and reactions.
For folks working in chemical research or manufacturing, a clear grasp of formulas like this sidesteps confusion and errors. With its three butyl groups hooked up to a central phosphorus atom doubled to an oxygen, tributylphosphine oxide isn’t just a mouthful — it’s genuinely useful. Labs across the globe use it as a ligand in coordination chemistry or a stabilizer in different reactions. Mistakes can happen if you guess or overlook the formula; it’s easy to add the wrong amounts or predict the wrong outcome in syntheses. Controlling quantities comes down to details like formula weights and elemental make-up — things you can’t skim over.
One of the best things about chemicals with well-understood formulas is reliability. In pharmaceutical research, for example, tributylphosphine oxide can help manage phosphorus-based reactions. You know exactly what’s in the bottle, so surprises during scale-up or quality control tests aren’t a constant threat. It saves time and money having recipes — even for so-called routine substances — that are fully checked and systemized.
Chemists who ignore the finer points of a formula risk more than a failed reaction. In my grad school years, a colleague misread a compound’s composition and produced unwanted byproducts. This set back the lab for a week. Reading labels and verifying formulae solves real problems.
Proper knowledge keeps labs and workplaces safer. Tributylphosphine oxide doesn’t spark with instability like some substances, but it offers lessons in vigilance. Handling any organophosphorus compound requires attention — oven temperature, reaction partners, even storage all need respect for what the formula tells you. Knowing C12H27OP is more than memorizing symbols; it’s about understanding what kinds of reactions might take place, or how the compound could break down.
Regulation also benefits from clear formulas. Auditors and safety inspectors expect up-to-date documentation. It’s not just bureaucratic — mistakes can ripple out with real-world costs. Simple diligence beats crisis control every time.
If chemistry education put more muscle behind formula literacy, problems would shrink. Digital tools now help students visualize molecules like tributylphosphine oxide in 3D. These models can turn memorization into genuine insight, making formulas matter beyond tests.
Sharing this knowledge keeps standards high. Reliable sourcing, careful measurement, and honest record-keeping all trace back to respecting the formula. Getting it right isn’t an academic exercise — it’s the basis for safer, smarter science.
In a chemistry lab, small choices add up. I’ve spent years at the bench, and I can tell you just grabbing any empty shelf for chemicals like Tributylphosphine Oxide leads to headaches down the road. This compound won’t explode if you look at it wrong, but don’t ignore the practical risks: it keeps its shape only until the wrong environment speeds up decomposition, contamination, and weird surprises in your next experiment. That’s not just bad science, that’s an unnecessary hazard.
Let’s look at facts, not just lab lore. Tributylphosphine Oxide earns a spot as “stable,” but put it in a hot, damp, or ultra-bright corner and you set the stage for trouble. Moisture creeps in, and air eventually reacts with the chemical. I’ve seen humidity turn powders into clumpy, unusable cakes. Once that happens, you’re not just risking a ruined sample; you’re running the risk of contamination during your work. The chemical industry and academic safety handbooks recommend closing the door on these nasties by using air-tight containers, and that advice holds for pros and students alike.
For most labs, the best place to keep Tributylphosphine Oxide is a cool, dry cupboard—away from sunlight and away from water sources like sinks or fume hood wash stations. Use a bottle with a tight seal; those wide-mouth jars everyone leaves half-open just invite moisture in. Glass or high-density polyethylene containers usually do the job. If your lab struggles with temperature swings, insulated cabinets work wonders.
Here’s a detail I learned the hard way: label your date of opening and always note if you see any signs of degradation. If the chemical smells different, or if the powder starts sticking together, it’s time to toss it or check with a supervisor. Cross-contamination is a real thing, and nobody wants mystery chemistry in their next batch.
Some forget ventilation checks until something smells strange. Make sure the storage space links to proper airflow—not a stuffy closet or a desk drawer. Even so, don’t daydream about “just keeping it in the fume hood.” Fume hoods protect you during use, not for storage. A chemical cabinet with a vent, if possible, does double duty—limiting vapor build-up and keeping the work space safe. Don’t tuck oxides next to acids or strong bases, either; accidental spills get ugly quickly.
Any good lab teaches storage as part of training, but I always urge folks to keep safety data sheets printed nearby. Even if you think you know a compound, standards change as manufacturers find new quirks or impurities. Periodic checks keep everyone alert. Sharing updates about protocol changes helps the whole group.
Institutions should invest in climate control and dedicated storage cabinets. If budgets are tight, simple dehumidifiers, regular inspections, and accountability logs provide a safety net. Encourage a culture where everyone checks on chemical supplies and points out problems right away. It only takes one mistake to cause damage, but habits set a foundation for trust and reliable results.
Tributylphosphine oxide shows up in several research and industrial settings, mostly because it brings value as a ligand, solvent, or extractant. Even though it isn’t usually a headline-grabber, it holds chemical properties that call for real care and attention. Many chemicals seem harmless until someone lands in trouble—eyes get irritated, lungs burn, or a simple spill turns into a safety scramble. At its core, safety isn’t about ticking boxes. It’s about keeping colleagues healthy and productive so work doesn’t stall due to a careless moment.
Working hands-on with tributylphosphine oxide, you’re facing a material that can bother skin, lungs, and eyes. Gloves and goggles should never be optional here. One splash in your eye or a whiff of dust can quickly lead to more than just discomfort. In my own experience, folks who cut corners or “just go quick” without their safety gear end up regretting it. I’ve helped clean up after those mistakes, and it never feels like time well spent. Respirators, while sometimes a chore, make sense if engineering controls can’t cut down airborne particles to safe levels.
This compound demands attention on the shelves too. Keep it in a tightly closed container, somewhere dry and well-ventilated. You can’t control every variable in a lab, but you can pick a storage spot out of direct sunlight and far away from flames or oxidizing agents. Spills can turn disastrous fast if tributylphosphine oxide gets mixed with reactive chemicals. Working in a fume hood isn’t overkill—odors can sometimes signal trouble, and a hood keeps the workspace safer for everyone.
No one plans for a spill, but sloppy response only makes it worse. Soak up the chemical with sand or an inert absorbent. Double-bag the material. Tossing it down the drain, like I’ve seen in a few underfunded facilities, isn’t just environmentally risky—it often lands the team in regulatory hot water. Follow local and federal hazardous waste guidelines and use proper labelling. People who ask for shortcuts usually deal with bigger problems down the line.
I’ve witnessed folks debate whether an emergency shower is worth it after a minor splash. Every minute counts. Strip off contaminated gear, rinse for at least 15 minutes, then seek medical advice. Same rules apply for inhalation—fresh air and oxygen bring relief, but don’t ignore lasting symptoms. Quick response limits harm and keeps recovery times shorter. This is as much about protecting your team as it is about your individual well-being.
Guidelines only matter if people follow them. Training shouldn’t be a once-a-year slideshow. Short refreshers, clear signage, and open conversations keep everyone focused. Supervisors set the tone. If leadership takes shortcuts, workers will, too. Labs with a good safety record usually owe that success to awareness and active participation at every level.
Switching to less hazardous alternatives is always worth exploring, even if it takes extra research or new protocols. Improved ventilation systems make a difference in older spaces. Lab audits by someone with a fresh perspective often reveal cracks in the armor. No matter how long you’ve worked with tributylphosphine oxide, complacency remains the hidden risk. Responsibility means more than compliance; it means looking out for each other so everyone gets home safe at the end of the day.
| Names | |
| Preferred IUPAC name | tributyl(phosphoryl)azane |
| Other names |
n-Butyltributylphosphine oxide
TBPO Tributylphosphine oxide |
| Pronunciation | /ˌtraɪ.bjuːˌtaɪlˈfɒs.fiːn ˈɒk.saɪd/ |
| Identifiers | |
| CAS Number | 1070-08-4 |
| 3D model (JSmol) | `3D Model (JSmol) string for Tributylphosphine Oxide:` `Tributylphosphine Oxide JSmol string: CCCC[P](CCCC)(CCCC)=O` |
| Beilstein Reference | 2813496 |
| ChEBI | CHEBI:39088 |
| ChEMBL | CHEMBL143202 |
| ChemSpider | 16221 |
| DrugBank | DB14524 |
| ECHA InfoCard | 54e54b72-5efe-41fb-8c3d-4b292592115b |
| EC Number | 208-760-7 |
| Gmelin Reference | 8779 |
| KEGG | C19624 |
| MeSH | D013983 |
| PubChem CID | 83068 |
| RTECS number | YQ9625000 |
| UNII | 1Y9FZ0J95Q |
| UN number | UN2810 |
| CompTox Dashboard (EPA) | DTXSID5020729 |
| Properties | |
| Chemical formula | C12H27OP |
| Molar mass | 290.41 g/mol |
| Appearance | White crystalline solid |
| Odor | Odorless |
| Density | D: 0.973 g/cm3 |
| Solubility in water | slightly soluble |
| log P | 1.06 |
| Vapor pressure | 0.00016 mmHg (25°C) |
| Acidity (pKa) | ≥28.0 |
| Basicity (pKb) | 8.93 |
| Magnetic susceptibility (χ) | -65.1·10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.455 |
| Viscosity | 1.81 mPa·s (25 °C) |
| Dipole moment | 4.53 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 387.8 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -723.9 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -5157.2 kJ·mol⁻¹ |
| Hazards | |
| Main hazards | Harmful if swallowed, causes skin and eye irritation, may cause respiratory irritation. |
| GHS labelling | GHS05, GHS07 |
| Pictograms | GHS06, GHS08 |
| Signal word | Warning |
| Hazard statements | H302, H319 |
| Precautionary statements | P280, P305+P351+P338, P337+P313 |
| NFPA 704 (fire diamond) | 1-1-1-0 |
| Flash point | 113°C |
| Autoignition temperature | 410°C |
| Lethal dose or concentration | LD50 (oral, rat): 1600 mg/kg |
| LD50 (median dose) | LD50 (median dose): Oral-rat LD50: 1800 mg/kg |
| PEL (Permissible) | Not established |
| REL (Recommended) | 1 mg/m3 |
| IDLH (Immediate danger) | Not established |
| Related compounds | |
| Related compounds |
Triphenylphosphine oxide
Trioctylphosphine oxide Triethylphosphine oxide Trimethylphosphine oxide Tributylphosphite |
