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Tris(trimethylsilyl) phosphite came onto the scene at a time when organophosphorus chemistry grew restless with older, less tunable building blocks. Folks in the labs wanted phosphorus compounds that sidestepped the baggage carried by traditional phosphites—reactivity too wild, handling too tricky, or byproducts that dragged down yields and hope. In the hands of chemists poking at every silicon and phosphorus corner, this compound outlined new territory. It forged a link between phosphorus and the trimethylsilyl group, a fragment that’s changed many games in silicon chemistry. Phosphorus's history stretches through basic fertilizers and nerve agents, but tris(trimethylsilyl) phosphite offered a less threatening kind of utility. Watching this compound move from academic curiosity to regular player in research catalogs spoke to how chemistry keeps retooling its toolkit, always shaping new answers from persistent questions.
Most folks outside labs never hear about tris(trimethylsilyl) phosphite. For the rest of us working closely with phosphorus ligands or custom-made silicon reagents, the molecule answers an old, nagging question: how do you introduce phosphorus into organic frameworks in a cleaner, more manageable way? The presence of three trimethylsilyl groups on the phosphite backbone means better volatility and less moisture sensitivity than earlier, clunkier relatives. This translates into fewer headaches with purification and a smoother ride in complicated multi-step syntheses. Where earlier phosphites stubbornly clung to water or broke down mid-reaction, this one carries more ballast against everyday lab nuisances.
Tris(trimethylsilyl) phosphite shows up as a clear, colorless to pale yellow liquid, flashing reminders that nothing fancy on the surface always means something special underneath. Its low viscosity helps experimentalists with precision, as measure-outs and transfers don’t get bogged down. The silicon atoms packed with methyl groups add heft and bulk, keeping the phosphorus more shielded, letting this molecule slip through reactions with a little less fuss than lighter, less protected cousins. Its chemical stability rides on the Si–O and P–O bonds, making the compound reactive enough to matter but not so jumpy that handling or storage feels like baby-sitting a tantrum-prone reagent. For anyone working with air- or moisture-sensitive methods, its lower tendency to pick up water keeps projects from derailing.
No two bottles of tris(trimethylsilyl) phosphite feel exactly alike. In the lab, purity makes or breaks a reaction, so seeing a trusted purity percentage on the label sends a small wave of relief. Every handling guideline matters, whether it’s the nudge to store in an inert atmosphere or reminders about compatible solvents. In my experience, clarity in these technical specs saves hours of troubleshooting that nobody writes about in their theses. Weight, density, boiling point—these aren’t trivia. They’re a scaffold built around experimental success, even when they seem like an afterthought next to the “hotter” properties some scientists chase.
Synthesizing tris(trimethylsilyl) phosphite doesn’t ask for wizardry, but it does reward those who care about detail. The process usually starts with phosphorus trichloride, which is as cantankerous as chemicals come, and chlorotrimethylsilane, a staple for anyone dabbling in organosilicon compounds. They react in the presence of a base, often a tertiary amine, to pull off the necessary chloride scrubbing. Controlling the addition rate, managing heat, and keeping the reaction in the right environmental bubble separates useable product from a mess of byproducts. Even in the best-equipped labs, every new batch finds some way to challenge assumptions, and that tension between established protocol and fresh obstacles sits at the core of chemical discovery. It’s not brute chemistry; it’s knowing where patience saves the day.
Tris(trimethylsilyl) phosphite stands out for more than its name. Researchers lean on it when they need a phosphorus transfer agent less prone to hydrolysis—especially in transition metal catalysis or designing ligand environments that balance steric protection with electronic tweaking. This reagent steps up in nucleophilic substitution and compounds involving gentle silylation, reacting smoothly with electrophiles that would chew up less protected phosphites. It partners well in reactions forming phosphonates and other phosphorus-containing fine chemicals. Watching a spectrum of possibilities appear, from organic synthesis to materials science, gave real weight to its versatility. Chemical tweaks on the basic structure—substituting silyl groups or altering the phosphorus oxidation state—keep discovering fresh territory for custom reagents and coordination complexes.
Anyone hunting for tris(trimethylsilyl) phosphite in the literature bumps into a list of aliases: P(OTMS)3, tris(trimethylsilyloxy)phosphine, or just TMS phosphite. Each synonym trails a backstory. P(OTMS)3 circles through organophosphorus articles as a shorthand, while the full IUPAC name signals formality, signaling to old guard chemists and regulatory circles that everyone’s aligned. These overlapping names make database searches feel like fishing in a crowded river, but they also tell a story: the more names a chemical wears, the more homes it finds in research journals and patents.
Venturing into chemical handling, especially with compounds featuring reactive phosphorus or silyl groups, sharpens the focus on safety. In real-world lab work, minor lapses brew major setbacks: skin contact, inhalation risks, or accidental spills all earn serious attention. The promise of improved stability with tris(trimethylsilyl) phosphite doesn’t erase the need for gloves, fume hoods, and hard training. Safety data sheets matter, but so do shared stories in the lab—like that time a rushed transfer cost a good pair of gloves and a sleeve. Reactive byproducts, low-level flammability, and environmental persistence keep the focus on responsible waste disposal and crisis planning, making operational standards more than bureaucratic speed bumps.
Applications for tris(trimethylsilyl) phosphite tend to land in high-value arenas: organic synthesis, pharmaceuticals, and advanced materials. In coupling reactions, its ability to introduce phosphorus quietly, with fewer disruptive side products, helps medicinal chemists move drug candidates forward. Materials scientists chase new polymer architectures or surface modifications relying on silylated phosphites because the reactivity profile fits intricate construction. Academic research digs into mechanistic studies enabled by phosphorus donors behaving with more predictability or unique spectral signatures. In my experience, watching how a single chemical enables such diverse creativity drives home how progress rarely comes from dramatic breakthroughs—most often, it comes from reliable building blocks showing up consistently.
Open any chemical literature from the past decade, and tris(trimethylsilyl) phosphite finds a steady, if not flashy, presence. Research keeps pressing into new phosphorus ligands, environmentally friendlier catalytic pathways, and more robust phosphorus-containing materials. Teams working on homogeneous catalysis and cross-coupling keep finding new reasons to tweak or revisit TMS phosphite as a reference or starting point. Each round of structural modification feeds into safer, more scalable reagents that edge closer to industry needs or regulatory shifts, showing once again how continual, patient development outpaces splashy innovations that seldom deliver on their promise across contexts.
Toxicology around tris(trimethylsilyl) phosphite sits in an odd space: not as infamous or thoroughly mapped as some old-school organophosphorus toxins but not entirely cleared for all handling scenarios. Early studies push for caution, echoing standard protocols about organosilicon and phosphorus compartmentalization. Animal testing and long-term persistence reviews show low acute toxicity compared to Industrial-era phosphorus hazards but signal room for deeper investigation. Accidental ingestion or chronic exposure risks still demand robust boundaries around usage and disposal. In my own group, extra safety drills and thoughtful controls kept uncertainty from turning into bad outcomes.
Looking forward, tris(trimethylsilyl) phosphite’s story keeps moving as researchers pick apart the silyl-phosphite axis for cleaner, greener reactions. Pushes toward milder syntheses, recyclable reagents, and modular building blocks often circle back to compounds like this one. As environmental pressures and regulatory hurdles grow steeper, the spotlight on less toxic, more predictable phosphorus pathways only brightens. The possibility exists that new substitutions or hybrid molecules drawing on the TMS phosphite scaffold will unlock niche uses in designer materials, bioactive compound synthesis, or electronics. For chemists, the next chapter always ties back to patient work—uncovering small advantages, learning from setbacks, and respecting the complex chemistry behind tools others might overlook.
Tris(trimethylsilyl) phosphite often pops up in synthetic chemistry labs. Its name alone can trip up a newcomer, but that sentence hides a useful and versatile compound. Chemists use it for preparing cleaner reactions and for manipulating phosphorous in tricky organic syntheses. The chemical formula—P(OSiMe3)3—breaks apart easily once you know what each part means. Here, "P" is phosphorus, "O" is oxygen, and "SiMe3" stands for trimethylsilyl, which itself is made up of a silicon atom bonded to three methyl groups.
Experience tells me that knowing a formula is not just about memorizing letters and numbers. In practical work, a chemical’s structure shows how it'll behave. For instance, with Tris(trimethylsilyl) phosphite, we’re not just looking at phosphorus surrounded by random groups. The bulky trimethylsilyl units protect the phosphorus atom, allowing chemists to use it under conditions that would destroy more fragile molecules. By looking at P(OSiMe3)3, I can tell it will act differently from simpler phosphites like trimethyl phosphite (P(OCH3)3).
Researchers rely on Tris(trimethylsilyl) phosphite for several reasons. In my time in the lab, it came in handy for making phosphorous-based reagents without unwanted byproducts. The presence of the three bulky trimethylsilyl groups lets it serve as a source of phosphite during organic transformations. Its relative stability compared to simpler phosphites helps keep reaction mixtures clean, which especially matters in pharmaceutical research, where purity is more than a goal—it’s a legal requirement.
The structure also matters in creating ligands and intermediates in organophosphorus chemistry. In a recent synthesis, a colleague and I noticed that using this phosphite made purification less of a nightmare—something anyone who’s worked with stubborn organic mixtures will appreciate. P(OSiMe3)3 doesn’t just do the job. It makes complex chemistry more manageable.
With a formula like P(OSiMe3)3, the different elements—phosphorus, oxygen, silicon, and carbon—remind us that safety shouldn’t get shortchanged. The compound hydrolyzes in water, giving trimethylsilanol and phosphorous acid, both of which need proper disposal. If I learned anything from handling these chemicals, it’s that even the cleanest-looking product still calls for a fume hood and eye protection. Too often, ignoring a small safety step leads to big problems. Chemists have a bigger responsibility—not just to themselves, but to the people around them and the environment.
With new developments in sustainable chemistry, reducing waste from phosphorus chemistry matters more every year. Simple tweaks in synthetic steps, like switching to less hazardous reagents, go a long way. Some labs now recycle side products, reusing the valuable elements and slowing the flow of chemical garbage headed to waste streams. Responsible sourcing and better disposal practices build trust in our work and reduce risks down the line.
Every formula tells a bigger story. In the case of Tris(trimethylsilyl) phosphite, understanding its makeup—P(OSiMe3)3—lets us make smarter decisions in the lab and encourages us to demand safe, ethical practice wherever chemistry is made.
Tris(trimethylsilyl) phosphite doesn’t show up in everyday conversations, but it has a regular spot in chemical research labs and production floors. I came across it a few years back while working on a project aimed at synthesizing some tailored organic molecules. What I remember most was its clear, almost slippery appearance and a sharp smell that never really leaves your mind, much like the way an early morning spent in a lab sticks with you.
This compound steps up in reactions where reductions and deoxygenations play a starring role. Most chemists who count on phosgene alternatives recognize Tris(trimethylsilyl) phosphite as a friendly helper for dehalogenation and reducing nitro compounds. The phosphorus atom in the molecule acts almost like a magnet for oxygen atoms, helping to strip them away from other molecules during synthesis. This makes producing delicate compounds a bit more straightforward, especially for those building complex pharmaceuticals or specialty polymers.
At several labs, I’ve seen Tris(trimethylsilyl) phosphite bridge the gap between basic and advanced chemistry. It allows reactions to proceed cleanly, which means fewer side products and easier purification. In practical terms, that leads to higher yields and less hassle cleaning up, something every chemist will appreciate on a long Friday evening.
Phosphorus ligands for catalysis don’t just pop out of nowhere. The compound comes in handy for crafting organophosphorus chemicals used with metal catalysts. For those working in organometallic chemistry—trying to get carbon to play nicely with metals—this reagent gives a precise, reliable phosphorus source. I once used it in a trial to synthesize ligands for a rare earth metal complex, and the process felt smoother than using older, less cooperative phosphites.
Research shows that it’s especially helpful in making air-sensitive phosphite esters. These often act as support players in transition metal catalysis found in both fine chemical and pharmaceutical production. That practicality grew on me the more I worked with air- and moisture-sensitive setups, knowing a single misstep could ruin an entire batch. The compound’s volatility and solubility in common organic solvents give researchers a good deal of flexibility during experiments.
In some cases, chemists want to introduce trimethylsilyl groups—those bulky, silicon-based protectors—to fragile sites in their molecules. Tris(trimethylsilyl) phosphite helps this process as a silylating agent. Silylation often crops up in the synthesis of protective groups because these bulky units shield parts of a molecule from unwanted side reactions. In my own work, adding these silyl groups felt less burdensome using this compound, particularly in crowded or sensitive chemical environments.
The compound reacts smoothly, allowing researchers to nudge tricky molecules in the right direction without fuss. Silylation not only saves time, it protects valuable starting materials from degradation and accidental loss, which matters when working with expensive or limited resources.
Handling Tris(trimethylsilyl) phosphite calls for care—it reacts strongly with water, produces flammable off-gases, and can irritate the skin. Labs that use it need solid protocols for storage and handling. While the compound itself carries risks, it has replaced harsher reagents in several processes, helping chemists follow greener, safer practices. Research continues on finding even milder alternatives, but for now, this phosphite offers a valuable mix of reactivity and control, especially for those aiming to minimize waste and maximize efficiency in modern chemical work.
Tris(trimethylsilyl) phosphite stands out in a chemist’s stockroom. This compound rarely stays stable in the open, and moisture or air exposure quickly triggers decomposition. On paper, chemical suppliers stamp warnings about reactivity, but you only need to work with it once to appreciate just how much it demands your respect. Sharp, pungent vapor escapes with sloppy handling and, in a tight space, really gets your attention. Reputable guides—like Sigma-Aldrich's technical sheets—keep this material flagged for its volatility and flammability. It's clear: take shortcuts, and you gamble with safety.
Sealed bottles with airtight closures matter. I’ve watched colleagues use parafilm or Teflon tape before putting containers back on the shelf. This works for short-term projects, but long-term storage takes more. A low-humidity, cool, well-ventilated cabinet—ideally an explosion-proof refrigerator—is my top recommendation. Just sticking bottles in a regular fridge near snacks or soft drinks breeds accidents nobody wants to explain.
Storing everything below room temperature slows down any lurking decomposition. Separate this phosphite from acids, oxidizers, and even minor traces of water; cross-contamination triggers unpredictable reactions. Double-containment, like using a desiccator or storing inside a secondary plastic tub, blocks accidental spills from spreading.
Practical experience leaves no illusions: you never want to breathe this stuff in. Work in a fume hood, every single time. Sometimes, I’ve seen new lab members underestimate the residue—a single drip on skin burns fast, so gloves (preferably nitrile or layered gloves) stay on for the entire handling process. Splash goggles and a lab coat protect from accidental contact. Changing gloves between steps keeps contamination in check.
If you spill, neutralizer and absorbent pads need to come out right away. No one wants to risk fire or chemical exposure. Don’t let old habits take over here—clean the area and yourself before leaving the hood. All waste, including gloves and wipes, should go straight into a dedicated sealed waste container.
No matter how many standard operating procedures you hang on the wall, nothing covers for experience and vigilance. A GC-MS technician taught me years ago to always announce what you’re opening when you work with these reagents. Good communication in shared lab settings prevents surprise mishaps. Hazard labels need to stick prominently on every container. Material Safety Data Sheets stay printed and close at hand, not just bookmarked deep in a computer.
Training every new researcher thoroughly before they so much as crack open a bottle keeps the whole lab safer. Involving experienced supervisors in these sessions creates opportunities for new staff to learn actual risks and smarter approaches instead of just checking boxes. Supervisors should encourage questions, since nothing slows down trouble like a well-informed team.
Ignoring these details doesn’t just damage research, it puts lives on the line. Injury reports and facility shutdowns always trace back to carelessness or missed steps. Proper management of hazardous chemicals isn't only about compliance or ticking off audits. It ties directly into the safety and well-being of everyone in the workspace. Safety practices with tris(trimethylsilyl) phosphite reflect a mindset—respect for chemistry, your colleagues, and yourself.
Anyone who’s spent time around organophosphorus reagents knows that some bottles demand a little extra respect. Tris(trimethylsilyl) phosphite belongs in that small club. Its chemistry looks simple on paper — a phosphorus atom hiding behind three trimethylsilyl groups — but this compound doesn’t take kindly to water or a careless hand in the lab. Too many folks get a rude introduction to moisture sensitivity here, watching a clear bottle cloud up or an intended reaction go sideways in the presence of the tiniest bit of water.
Phosphites like this one react directly with water. The trimethylsilyl groups, which act as shields for the central phosphorus, come off pretty fast under wet conditions. Water breaks the compound down, leaving behind silanols and phosphorous acid. This isn’t a slow, background nuisance. Expose tris(trimethylsilyl) phosphite to humid air, and active chemistry gets underway right away — heat, fumes, and a gunky mess will follow.
Researchers at the bench see flakes and cloudiness where there was clarity. Problems don’t just stop at the ruined reagent. Unintended byproducts sneak into syntheses, metal-catalyzed couplings stall, yields tumble, and the troubleshooting begins. In my own graduate lab days, one hour in a poorly sealed vial led to an experiment that ended before it began. Ask around at any research group with a focus on phosphite chemistry, and you’ll hear plenty of stories about reactions lost to a day of summer humidity.
Moisture gets a lot of attention, but plain old oxygen in the air isn’t a friend either. Many phosphorus(III) compounds, including this one, will slowly oxidize on standing. That means storage conditions must be tight — think sealed under argon, not just a loosely screwed cap on the shelf. In a large industrial setting, leaks or bad fittings lead to spoiled drums worth thousands. At the bench, a quick dash from glovebox to reaction flask might doom a rare sample. Even trained chemists occasionally misjudge how much care to take until too late.
Practicing scientists often rely on the CRC Handbook or Sigma-Aldrich technical sheets. These sources don’t mince words: “Sensitive to moisture and air.” One study published in Synthesis measured phosphite decomposition after brief humid exposure, with almost total hydrolysis in less than an hour at typical room temperature. This isn’t theoretical — it’s measured with gravimetric analysis, NMR, and confirmed by reproducible failed reactions worldwide. No point pretending it’s stable; the risks are well established in both academic papers and chemical safety documentation.
There’s no magic fix, just some hard-earned best practices. Chemists store the material under dry, inert gas, often in gloveboxes filled with argon or nitrogen. Opening a bottle happens only inside these boxes, or at least with a steady stream of dry gas blanketing the neck. For small labs without a glovebox, extra precautions help: fresh aliquots, tight septa caps, and pressure-equalizing tubes filled with desiccant. Some researchers keep entire reagent kits double-bagged with silica gel, changing the gel between uses. The time saved by this investment pays off with every successful synthesis that runs to completion instead of failure.
Moisture and air sensitivity carry real consequences. A solid understanding of why this happens, plus careful handling, makes the risks manageable. Tris(trimethylsilyl) phosphite forces us all to remember the rules of sound lab practice and gives more than a few a painful lesson in chemical humility.
Some chemicals barely make a ripple, but Tris(trimethylsilyl) phosphite shouldn’t be one of them. Folks in research and industry often cross paths with it, mostly for making ligands or trying new synthesis tricks in the lab. It gives off vapors and those don’t ask permission before irritating your eyes, nose, or throat. Anyone who has handled silanes or phosphorus compounds knows there’s always a sting in the air you notice too late. The stuff also catches fire, sometimes just from a spark or if it bumps up against strong oxidizers. Water won’t put this out easily since hydrolysis makes things even riskier—forming flammable gases you don’t want near an open flame or toggle switch.
Nobody who’s spent a few long days in a chemistry lab doubts the dangers. Skin contact leaves your hands tingling or red, sometimes blistered if you wait too long to wash it off. Vapors send you coughing or leave your eyes burning, and for anyone with a twitchy airway or asthma, every breath feels heavier. Once a friend left a small bottle open a bit too long, thinking a minute wouldn’t matter—ended up with headaches and a stinging nose that lasted hours. Accidents pick on both the clumsy and the cautious.
Eyes take the hit first in most labs—fumes or splashes both sting. If this happens, start flushing with plenty of water right away, holding eyelids open. Eye wash stations aren’t just for decoration. It takes at least 15 minutes to rinse off these burns. For splashes on skin, pull off contaminated clothing, get under the shower, and scrub with soap and running water. Trying to tough it out brings misery and risks scars or chemical burns. If someone breathes in a dose, get them into the fresh air as soon as possible. Feeling dizzy or short of breath? That’s not just nerves. Oxygen sometimes helps, and serious breathing trouble means a trip to the emergency room.
Lab routines matter. Anyone handling this stuff needs gloves that don’t tear easily, goggles with a snug fit, and a fume hood with good airflow. Open bottles only inside the hood. Spills always surprise you, but absorbents in a spill kit cut down on panic. Never mix this compound with acids or oxidizers. Labeling bottles, keeping records, and walking through emergency drills don’t sound flashy, but they stop mistakes from turning worse.
Some numbers stand out. The Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health agree that exposure limits need to be low due to potential respiratory and skin sensitization. Inhalation of even modest amounts leaves folks coughing and feels far worse in a closed space. The European Chemicals Agency flagged this compound for skin and eye damage, and also notes its fire risk. Nobody in a small business or university lab ignores these recommendations and keeps getting lucky.
Safer alternatives sometimes work, but not every job allows substitutes. Investing in better ventilation and spill response gear saves headaches and hospital bills. Training new folks, even if they claim experience, closes gaps in safety. Emergency plans written out and reviewed each year catch problems before they escalate. The goal stays the same: turn hard rules into muscle memory so everyone goes home the same as they arrived.
| Names | |
| Preferred IUPAC name | Tris(trimethylsilyl) phosphite |
| Other names |
Phosphorous acid tris(trimethylsilyl) ester Tris(trimethylsilyl) phosphite Trimethylsilyl phosphite Phosphorous acid tris(trimethylsilyl) ester TMS phosphite |
| Pronunciation | /ˌtrɪsˌtrɪˌmɛθ.əlˈsɪl.i ˈfɒs.faɪt/ |
| Identifiers | |
| CAS Number | 920-64-5 |
| 3D model (JSmol) | `3D model (JSmol)` string for **Tris(trimethylsilyl) phosphite**: `C[Si](C)(C)OP(O[Si](C)(C)C)O[Si](C)(C)C` |
| Beilstein Reference | 1867413 |
| ChEBI | CHEBI:87377 |
| ChEMBL | CHEMBL4299913 |
| ChemSpider | 21420898 |
| DrugBank | DB11262 |
| ECHA InfoCard | 03d1c9b2-a2e1-43d4-bf42-cfceb7faad50 |
| EC Number | 248-854-7 |
| Gmelin Reference | 83387 |
| KEGG | C14310 |
| MeSH | D014242 |
| PubChem CID | 68157 |
| RTECS number | TG4025000 |
| UNII | 7GNO08U1QQ |
| UN number | UN3264 |
| CompTox Dashboard (EPA) | DTXSID9044363 |
| Properties | |
| Chemical formula | P(OSiMe₃)₃ |
| Molar mass | 352.62 g/mol |
| Appearance | Colorless liquid |
| Odor | Odorless |
| Density | 0.835 g/mL at 25 °C |
| Solubility in water | insoluble |
| log P | 1.8 |
| Vapor pressure | 0.8 mmHg (25 °C) |
| Acidity (pKa) | 28.0 |
| Basicity (pKb) | 12.7 |
| Magnetic susceptibility (χ) | -84.0e-6 cm^3/mol |
| Refractive index (nD) | 1.419 |
| Viscosity | 10 cP (20 °C) |
| Dipole moment | 3.17 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 415.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -1328.05 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -2459 kJ·mol⁻¹ |
| Pharmacology | |
| ATC code | Not assigned |
| Hazards | |
| GHS labelling | GHS02, GHS07 |
| Pictograms | GHS02,GHS07 |
| Signal word | Warning |
| Hazard statements | H226, H302, H312, H332, H319 |
| Precautionary statements | P210, P233, P240, P241, P242, P243, P260, P264, P271, P280, P301+P310, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362+P364, P370+P378, P403+P235, P405, P501 |
| NFPA 704 (fire diamond) | 1-2-1-React |
| Flash point | 74 °C |
| Lethal dose or concentration | Lethal Dose (LD50, oral, rat): 1600 mg/kg |
| LD50 (median dose) | LD50 (oral, rat): 1600 mg/kg |
| NIOSH | TT2975000 |
| PEL (Permissible) | PEL not established |
| REL (Recommended) | 10 mg/m3 |
| Related compounds | |
| Related compounds |
Trimethylsilyl iodide Trimethylsilyl chloride Hexamethyldisilazane Triphenyl phosphite Phosphorus trichloride |
