Tetrabutylammonium Bromide: A Comprehensive Commentary
Historical Development
Tetrabutylammonium bromide walked onto the stage following the discovery and rising use of quaternary ammonium salts in organic chemistry during the late twentieth century. The focus on transferring ions between organic and aqueous layers set the pace. Chemists demanded compounds that could cut through solubility issues in the lab, so researchers turned to cationic salts. Over decades, this substance found footing through repeated trials, practical adjustments, and feedback from countless reaction benches around the world. Today's manufacturers rely on patterns set by those early years, pulling from a playbook built through hands-on solutions and mid-century industrial optimism. Improvements to yield, purity, and cost made tetrabutylammonium bromide a regular feature in both academia and industry.
Product Overview
The salt comes as a white crystalline powder, though sometimes you find it in slightly off-white form depending on the grade and manufacturer. Easy enough to scoop, measure, and dissolve, it handles well during bench work, glassware transfers, and mass production runs. Packaging usually features sturdy containers with a moisture-tight seal. Regular labeling displays chemical name, synonyms, and crucial handling info—needed by everyone from seasoned chemists to new lab techs. In my experience, any delays or confusion with this salt usually trace back to poor labeling or misjudged storage, a direct nod to why clear product descriptors matter so much.
Physical & Chemical Properties
Tetrabutylammonium bromide falls into a safe melting window, beginning to liquefy at about 103–107°C. It dissolves in water, alcohols, and some polar organic solvents, but stays solid at room temperature unless paired with strong acids or bases. The physical feel is a waxy powder or small, distinguishable crystals, though in humid air you can pick up a faint chemical scent—and moisture clings to the surface if neglected. The chemical stability helps in storage and shipping, but the quaternary ammonium structure makes it eager to interact with various ions in double-layered reactions or as a phase-transfer catalyst.
Technical Specifications & Labeling
Purity levels usually reach 98% or higher, and certificates often display results straight from chromatographic testing and spectrometric validation. The best labs demand tight moisture limits, below a few percent, and strong controls with heavy metal contaminants and trace ions. Some suppliers include lot numbers, expiration dates, and digital QR codes for traceability. Reliable warning icons, tightly-worded hazard phrases, and thorough preparation guidelines accompany nearly every vial or drum I’ve come across. This keeps both small academic shops and full-scale plants in line with legal and safety standards.
Preparation Method
Manufacturing starts with reaction between tetrabutylammonium hydroxide and hydrobromic acid, under cooling and stirring to control runaway exothermic heat. Clean isolation through filtration, then water removal with vacuum drying, delivers a solid product, ready for refinement and packing. While this method dominates because of its yield and cost-balance, repeated washing and recrystallization get extra attention in labs sensitive to impurities, like in pharma or electronics. The hands-on technique matters, as cutting corners increases water content or introduces unwanted byproducts that complicate downstream chemistry.
Chemical Reactions & Modifications
Tetrabutylammonium bromide paves the way for phase-transfer catalysis, especially in nucleophilic substitution and oxidation reactions. Its bulky four-carbon arms and ionic core make it a shuttle for anions across barriers, something I’ve seen transform slow, multi-hour syntheses into quick, dependable reactions. Modifying the structure by swapping out bromide for other halides or tailoring the alkyl chains leads to new properties, from altered solubility to different melting points, letting chemists tweak formulas for unique environments—electroplating or extraction included.
Synonyms & Product Names
Beyond its International Union of Pure and Applied Chemistry name, people recognize it as TBAB, N,N,N-tributyl-1-butanaminium bromide, or simply tetrabutylammonium bromide. Product codes vary from one catalog to another, but the most universal naming boils down to abbreviations like TBA bromide or “quaternary ammonium compound, butyl, bromide.” Proper synonym tagging across safety sheets and digital inventories matters for avoiding errors, especially when ordering, cataloging, or searching compound databases in places with multilingual teams.
Safety & Operational Standards
Handling Tetrabutylammonium bromide means you run chemical nitrile gloves, splash-resistant goggles, and a snug lab coat. Work gets done in well-ventilated fume hoods, and I’ve watched serious labs mandate chemical hygiene plans that stop small mistakes from snowballing. Safety Data Sheets caution against inhalation and skin contact, while local fire codes rate storage rooms for dry, cool, and tightly closed conditions. Spill protocols in both university and industrial settings depend on fast cleanup with absorbent pads and disposal through certified waste streams, not a regular trash bin. Training and drills, reviewed at least yearly, back up these guidelines.
Application Area
Tetrabutylammonium bromide doesn’t feel limited to a single use. Chemists pick it up for phase-transfer catalysis, electrochemical analysis, organic synthesis, or extraction procedures. It finds a place in pharmaceuticals—whether building blocks or intermediates—in dye manufacture, and in green chemistry projects such as aqueous biphasic systems. Some labs use it for DNA extraction or to purify proteins in biological research. Each of these settings looks for reliable, easy-to-handle materials that deliver speed and reproducibility. From my years at the bench, the salt’s consistency keeps it in regular rotation, never gathering dust on storage shelves.
Research & Development
Work keeps moving forward, as teams look for greener synthesis methods using less solvent, milder conditions, or alternative starting materials. Efforts target fine-tuning these quaternary salts for higher reaction efficiency without piling on hazardous waste or unwanted byproducts. Large R&D groups model reactions by advanced software, and then validate on the bench, pushing for ways to dial up reactivity or selectivity. In battery research and nanotechnology, modifications to the basic TBAB skeleton anchor whole new families of ionic liquids and advanced materials, bringing in energy storage and environmental applications that didn’t seem possible even a decade ago.
Toxicity Research
Scientists keep watching for hidden risks, since even trace contamination of pharmaceuticals or food products triggers strong regulatory blowback. Current toxicological studies show low oral toxicity in rodents, but reports highlight possible irritation from dust or concentrated exposure to skin and eyes. Environmental scientists raise questions about persistence once spilled or dumped, with quaternary ammonium compounds linked to bioaccumulation or aquatic risk. Regulatory action sometimes leans on these findings, so ongoing work fills in the data gaps—defining thresholds for workplace exposure and handling procedures. First-hand, I’ve seen regular health-risk updates trigger shifts in lab policies or push a lab leader to switch suppliers.
Future Prospects
Many believe that green chemistry pushes—especially the shift from hazardous metals to cleaner, recyclable chemicals—will increase TBAB’s role as a phase-transfer agent and electrolyte. Improved production with renewable inputs stands as a near-term goal for both small and bulk producers. New uses in organic electronics, ionic liquid design, or carbon capture provide exciting research ground, powered by fresh government funding and international collaboration. If safety data keeps expanding and recycling gets cheaper, these salts might become mainstays well beyond traditional organic synthesis, powering labs as well as next-generation industrial technologies. My view leans optimistic: each technical leap rests on solid chemical basics, a reputation for reliability, and steady user feedback from workers who handle the stuff every day.
The Backbone of Many Bench Experiments
Bottle after bottle of tetrabutylammonium bromide—better known as TBAB—lines the shelves of modern chemistry labs. TBAB does not carry the high profile of famous catalysts or life-changing drugs featured in headlines, but it keeps a quiet importance among researchers. Labs reach for TBAB when experimenting with difficult reactions, especially those involving two liquids that famously do not mix, like oil and water. Many years spent as a research assistant taught me to spot TBAB in any well-equipped organic chemistry lab, always ready for moments when researchers stretch the limits of old chemical reactions.
Bridging Phase Transfer Gaps
Scientists run into trouble if they try to make chemicals react in mixtures where the ingredients never meet. TBAB brings something special to the table: it helps shuttle ions between water and organic solvents. This trick allows reactions to happen efficiently, even if the reactants normally avoid each other. Researchers call this ability “phase-transfer catalysis,” and TBAB stands out as one of the go-to options. For example, it becomes handy during the manufacture of pharmaceuticals, agrochemicals, and dyes. With a sprinkle of TBAB, the yields of certain reactions improve, sometimes to the point that an industrial process becomes profitable.
Beyond Industry: Everyday Academic Research
I remember grad students improvising with TBAB when textbooks suggested nothing worked. Its structure—a bulky ammonium ion wrapped in butyl groups—gives it a talent for dissolving in both water and organic solvents. That’s why chemists pull it off the shelf when they need to push tough alkylations, oxidations, or even some polymerizations past the finish line. Synthetic chemists rely on it in the education sphere too, as it shortens lab days spent tinkering with immiscible phases and waiting for sluggish reactions to finish.
Environmental and Safety Considerations
With widespread use comes a responsibility to manage waste and assess safety. TBAB holds up as a relatively stable and non-volatile compound, easing worries over inhalation risks. At the same time, it doesn't break down easily in nature, so chemists must dispose of it thoughtfully. Environmental chemists already study its effects on aquatic life, urging labs to reduce releases into wastewater streams. Green chemistry circles recommend TBAB as a safer alternative to some older phase-transfer catalysts, but this suggestion always rides alongside a call for careful waste management. Labs storing TBAB lock it away from acids and oxidizers, following clear guidelines that protect workers from mixing incompatible chemicals.
Looking for Better Solutions
Researchers and chemical manufacturers do not sit still. They look for newer compounds that work better or break down easier in the environment. Still, replacing TBAB across the board takes time and evidence, since it delivers reliable results in a wide range of applications. While companies investigate biodegradable alternatives, TBAB keeps its place in the toolkit. I’ve watched its use move from academic projects to large-scale manufacturing runs, always proving its worth as long as people manage its risks and handle it responsibly.
Final Thoughts
TBAB’s success comes from solving real laboratory headaches, helping researchers coax stubborn metathesis reactions off the ground, and smoothing paths toward higher yields. Its widespread adoption reflects both its strengths and the continued power of small innovations in pushing chemical science forward. People in chemistry value not only the glamour of new discoveries but also the humble compounds that help get the job done, again and again.
What Tetrabutylammonium Bromide Really Is
Ask any researcher about tetrabutylammonium bromide, and you’ll likely get a confident answer: C16H36BrN. At first glance, this string of letters and numbers can seem pretty dry. But beneath that formula sits a useful tool for chemists, students, and even folks finding their way in new synthetic territory. I remember fumbling over formulas in the lab, double-checking notes to make sure I hadn't mixed up butyl chains or left out a hydrogen. It's easy to take a shortcut and copy the formula off a label rather than asking why its arrangement matters.
Why C16H36BrN Deserves Attention
Every part of this molecular formula tells a story. Those sixteen carbons and thirty-six hydrogens come from the four butyl groups (four carbons each), attached to a central nitrogen. Bromine steps in as the counter ion, forming a salt. Textbooks show a neat model, but real-life uses show just how much difference a simple formula can make. This particular salt acts as a phase transfer catalyst. It shuttles ions between solvents in organic reactions, easing stubborn transitions and boosting reaction rates.
Industry leans on tetrabutylammonium bromide for more than textbook demonstrations. Small-scale labs love it for straightforward syntheses. In pharmaceuticals, the compound mediates reactions that might otherwise drag on for hours or fail due to the solubility wall between ingredients. Its molecular structure offers just enough bulk and charge to manage these jobs smoothly, whether separating organic and inorganic layers or taming unwieldy reactants.
Getting the Facts Right
Accuracy in reporting a chemical formula is not just an academic formality. Misreporting C16H36BrN as something less or more—by mixing up numbers or elements—can mean a failed experiment, unexpected toxicity, or even a safety incident. I once worked on a group project where someone misread the formula, leading to a whole batch heading in the wrong direction. Double-checking the structure and notation saved that day, but only after hours lost.
Mistakes happen. Even major suppliers sometimes get feedback from buyers about misprints in datasheets. Any research that builds on shaky chemical information could waste precious time or resources. In an age where misinformation spreads fast, sticking to primary sources—peer-reviewed journals, up-to-date reference books, and certified product labels—keeps everyone on track.
Supporting a Better Chemical Culture
Better chemical literacy goes beyond knowing formulas. Taking the time to understand why one compound behaves differently from a close cousin encourages questions about safety, environmental impact, and innovation. I have seen students realize a molecular formula is more than a set of numbers: it signals risk levels, storage needs, and handling practices all at once.
Tackling errors requires direct action—peer review, team cross-checks before running reactions, even technology like scanning QR codes to verify products. Open communication strengthens trust among researchers, suppliers, and regulators. The habit of double-checking seems small, but it adds up across labs and classrooms.
Making Chemistry Personal and Practical
For educators, emphasizing the meaning behind C16H36BrN sticks with students far longer than rote memorization. For scientists in the field, respecting the implications carried by a simple formula keeps experiments safe, data accurate, and innovation moving forward. In this way, molecular notation moves from a static label to a living part of the scientific process—every number earned, every letter essential.
Why Storage Practices Matter
Tetrabutylammonium bromide, often called TBAB in labs, turns routine chemistry into a real safety concern if left lying around carelessly. This white solid doesn’t explode at the slightest mistake, but it draws in water from the air and starts clumping up in a heartbeat. Clumped TBAB dissolves slowly and gives uneven results—never mind the mess it leaves in a bottle. I once left an open jar in a humid storeroom for a weekend. By Monday, the material felt like soggy sugar and failed the next reaction.
Humidity Wrecks Quality Fast
Humidity isn’t just uncomfortable during summer. With TBAB, even a moderately moist room can lead to costly waste. The chemical acts hygroscopic, meaning it pulls water from the air—something I learned during a rainy spell at the lab. Most experiments that rely on TBAB count on accurate amounts. Water hitching a ride on every gram of TBAB throws off calculations, which ruins outcomes in synthetic or analytical chemistry.
Proper storage starts with sealing. Always close the bottle tightly after scooping, never trusting a loosely twisted cap. I prefer bottles with rubber gaskets. Free-flowing powders come out easier and make weighing less of a headache.
Temperature Makes a Difference
Warm conditions speed up degradation or promote caking. TBAB won’t burn through a shelf, but higher temps speed up reactions with moisture or any stray traces of other chemicals. I keep my bottles in a cool cabinet, away from sunlit windows or steamy radiators. A lab fridge isn’t always necessary, but storing at room temperature below 25°C keeps TBAB solid and dry. Make sure not to stick the bottle next to liquids or acids either—a spill could ruin the whole batch.
No-Nonsense Labeling and Segregation
Mislabeling may sound basic, but I’ve seen high school, university, and even professional labs trip up on this one. A faded cap or missing date leads to confusion, especially when powders clump. Clear labels with name, date received, and concentration (if pre-mixed) cut down on mistakes and prevent unnecessary opening of multiple bottles. I learned to use waterproof markers, and I update labels if something—like moisture exposure—changes the chemical’s appearance.
Avoiding Cross-Contamination
Spoons, spatulas, or even gloves with residue from other chemicals don’t belong in the bottle. A friend of mine once returned a spatula with traces of an acid, which turned part of their TBAB into sludge by the next week. Use a clean, dry scoop every single time. Keep the bottle closed in between uses, and never pour excess back—discard it without second guessing, rather than risk contaminating the main supply.
Disposal and Old Stock
Old or discolored TBAB gives unpredictable results. If in doubt, dispose of leftovers following local hazardous chemical rules. I always separate waste into dedicated containers and avoid pouring anything down the sink, as many places require controlled disposal.
Takeaway for Home and Lab
Good habits with storage aren’t about perfection—they keep workers safe and save time and money. If you respect TBAB’s quirks and treat the powder with care, projects run smoother, waste drops, and safety improves. That dedication sets professionals apart from amateurs, whether working in a high-tech lab or a modest college storeroom.
Looking Beyond the Lab Bench
Tetrabutylammonium bromide doesn’t show up in weekend kitchen experiments or the average high school chemistry set. Folks who enter specialty labs or work with advanced materials see its name more often. It functions as a quaternary ammonium salt, often used for phase-transfer catalysis. Despite the complicated title, it’s a helper for certain chemical reactions—nothing fancy to the eyes of those outside of chemical industries or academic settings.
Hazard Labels: Not Just for Show
The safety sheet of tetrabutylammonium bromide gives clear warnings. If you hold it under a microscope, it looks fairly harmless. Shift that view to a human body, though, and the story changes. If swallowed, this chemical can cause anything from digestive irritation to much more serious trouble, like nausea or vomiting. Eyes and skin get irritated on contact, sometimes severely. Breathe in too much? Possible coughing and trouble breathing. It doesn’t act as a silent partner in a lab; it makes its presence known if handled carelessly.
Workplace Experience: Lessons from the Ground
In my years bumping elbows in research labs, I learned fast that respect for these substances pays off. One colleague reached for a tube, forgot gloves, and got a nasty skin rash. Another had the misfortune of a spill near his workbench. He ended the day in the safety shower, regretting shortcuts. Proper ventilation, gloves, eye protection, lab coats—any seasoned worker soon views these as second nature, not overkill.
Not Just a Personal Matter
The risks don’t close their doors after the lab bell rings. Waste management brings its own set of headaches. Pouring these chemicals down the drain pitches a long-term problem for wastewater treatment plants, potentially disturbing aquatic life downstream. Environmental impact gets real quick when solvents or intermediate compounds go unnoticed or enter the wrong disposal path. I’ve seen universities caught in regulatory headaches after a few gallons escaped down the wrong pipe.
What the Science Says
Studies confirm that tetrabutylammonium bromide poses a low risk for acute toxicity compared to true heavyweights like cyanides or mercury salts. The main problems stem from skin and eye irritation, sometimes respiratory issues with dust or high concentrations. Chronic exposure rarely makes headlines, but no one’s risk appetite should expand just because severe hazards aren’t front and center.
Building Safer Habits
The fix begins long before handling the chemical. Training sessions help, but actual, practical reminders—signs by the fume hood, gloves always stocked, PPE checks—stop accidents before they bloom. Emergency showers, eye wash stations, and filing incident reports aren't wasted precautions. These drills keep the team sharp, not just compliant.
Keeping Tetrabutylammonium Bromide in Check
Laws and industry rules don’t just spring up by accident. The REACH and OSHA regulations call for clear labeling, limited handling, and proper storage. Storing tetrabutylammonium bromide in airtight containers, away from acids or oxidizers, greatly lowers incident risk. I’ve watched teams bring down accident rates by keeping Material Safety Data Sheets easy to find and using a “buddy system” for tricky procedures. A culture of accountability, from students to senior researchers, builds a safer workplace.
Looking Ahead
No one aims for dramatic accidents or unexpected hospital trips. The foundation is clear: informed handlers, strong waste protocols, respect for chemical power. Tetrabutylammonium bromide isn’t the villain of the lab—ignorance and shortcuts are. The real hazard doesn’t show up until safe habits get skipped.
Considering Everyday Chemistry
Tetrabutylammonium bromide doesn’t get splashed across news headlines, but it shows up frequently in labs everywhere. With its long organic chains and a bromine counterion, Tetrabutylammonium bromide acts like a workhorse for chemists. Let’s talk about its tangible traits.
Solid Form and Appearance
Open a container, and you’ll find it as a white, crystalline powder. That powder clings to glassware and spills like flour—light, airy, not sticky. Each granule holds its shape until moisture comes into play; a humid room turns it clumpy. That spells trouble for storage. Labs use tightly sealed bottles with desiccants tossed in. In the world of chemicals, hydroscopic ones like this demand respect.
Solubility That Gets Noticed
Water barely fazes some salts, but Tetrabutylammonium bromide dives right in. It stirs into water with ease, creating a clear solution. Toss it into organic solvents like acetonitrile, methanol, or dichloromethane, and it mixes well there too. This quality matters to researchers who want their reagents dissolved, not stuck as lumps at the bottom of a flask. In my own undergraduate organic syntheses, nothing slowed down an experiment like undissolved salts. Tetrabutylammonium bromide always did its job: into the beaker and blended in fast, no headaches.
Melting Point and Stability
Pop some of this salt on a melting point apparatus—reports show it gives way somewhere between 102-105°C. Above that, the solid softens and pools into a liquid. Below room temperature, it stays stable and inert. You can store it on a shelf all year and not fret about significant breakdown, so long as moisture stays out. Chemical stability often shapes whether something lives in a fridge, freezer, or benchtop; Tetrabutylammonium bromide wins a spot at room temperature.
Handling and Safety
Even stable solids must get handled with care. Tetrabutylammonium bromide raises fewer alarms than volatile acids or solvents, but gloves and goggles always make sense. The MSDS advises that people avoid direct contact or inhalation. It’s only polite to treat any lab chemical with respect. In shared spaces, I saw plenty of accidents from folks who thought a white, odorless solid couldn’t be hazardous.
Odor and Taste (Not for Sampling!)
Here’s a point for context—though the salt has no strong odor, tasting is out of the question. My time in the lab showed me how often curiosity can turn dangerous. No experienced chemist would try to taste their reagents. The odorless quality sometimes tricked newcomers into thinking it harmless. No aroma doesn’t equal no risk.
Reflecting On Why These Properties Matter
Reliable performance draws chemists to Tetrabutylammonium bromide. Its solid form, high solubility, and stability let researchers plan without backup plans or contingency orders. Labs cut down on troubleshooting thanks to physical consistency. The main solution to clumping or degradation: use dry containers, keep samples away from humidity, rotate stock. These seem simple, but without the right habits, purity drops and results get muddied.
As chemical supply chains see greater scrutiny, knowing a compound by the grip of its crystals in your hand—not just by a catalog listing—helps ensure quality in every experiment. Tetrabutylammonium bromide isn’t spectacular; it’s reliable. Reliable counts for a lot in chemistry and in life.


| Names | |
| Preferred IUPAC name | tetrabutylazanium bromide |
| Other names |
TBAB
Tetrabutylazanium bromide TBA Bromide N,N,N-tributylbutan-1-aminium bromide |
| Pronunciation | /ˌtɛ.trə.bjuːˌtaɪl.əˈmoʊ.ni.əm ˈbroʊ.maɪd/ |
| Identifiers | |
| CAS Number | 1643-19-2 |
| 3D model (JSmol) | `3D structure; JSmol model string: "CC[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]"` |
| Beilstein Reference | **1718738** |
| ChEBI | CHEBI:38503 |
| ChEMBL | CHEMBL1506 |
| ChemSpider | 27243 |
| DrugBank | DB11127 |
| ECHA InfoCard | 100.231.893 |
| EC Number | 208-089-7 |
| Gmelin Reference | 72988 |
| KEGG | C14319 |
| MeSH | D017978 |
| PubChem CID | 8663 |
| RTECS number | WN9823000 |
| UNII | N9NRQ6J11V |
| UN number | Not regulated |
| CompTox Dashboard (EPA) | DTXSID4059797 |
| Properties | |
| Chemical formula | C16H36BrN |
| Molar mass | 322.37 g/mol |
| Appearance | White crystalline powder |
| Odor | Odorless |
| Density | 1.039 g/cm3 |
| Solubility in water | soluble |
| log P | 0.56 |
| Vapor pressure | Negligible |
| Basicity (pKb) | 4.9 |
| Magnetic susceptibility (χ) | −6.1×10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.493 |
| Viscosity | 370 cP (20°C) |
| Dipole moment | 6.463 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 322.8 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | −360.2 kJ·mol⁻¹ |
| Pharmacology | |
| ATC code | T01AX01 |
| Hazards | |
| Main hazards | Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. |
| GHS labelling | GHS07, Warning, H315, H319, H335 |
| Pictograms | GHS07 |
| Signal word | Warning |
| Hazard statements | Harmful if swallowed. Causes serious eye irritation. Causes skin irritation. |
| Precautionary statements | P264, P270, P273, P301+P312, P305+P351+P338, P330, P501 |
| NFPA 704 (fire diamond) | NFPA 704: 1-0-0 |
| Flash point | > 102 °C |
| Lethal dose or concentration | LD50 (oral, rat): 2500 mg/kg |
| LD50 (median dose) | LD50 (median dose): >5 g/kg (oral, rat) |
| NIOSH | XN8575000 |
| PEL (Permissible) | Not established |
| REL (Recommended) | 10 mg/m3 |
| Related compounds | |
| Related compounds |
Tetrabutylammonium chloride
Tetrabutylammonium iodide Tetrabutylammonium fluoride Tetrabutylammonium hydrogen sulfate Tetrabutylammonium perchlorate |