Bromoacetyl Bromide: From Historical Curiosity to Modern Reagent
Historical Development
Bromoacetyl bromide entered the chemist’s toolkit during the flurry of halogen compound exploration in the late nineteenth century. Back then, early researchers like Victor Meyer and his peers probed halogen reactions and stumbled onto derivatives like bromoacetyl bromide while mapping out the chemical landscape. The ability to introduce functional groups with precision changed the rules for synthetic chemistry. Early applications stayed pretty limited, mostly academic, but over time, industry started pulling compounds like this into more practical uses. The interest in organobromine compounds grew as pharmaceuticals and crop science demanded new building blocks, and bromoacetyl bromide’s unique reactivity gave it a strong claim over certain synthesis steps.
Product Overview
Describing bromoacetyl bromide, you’re looking at a colorless to pale yellow liquid. A strong smell hits anyone who’s opened its bottle. As a bifunctional halide, it brings both a bromo and a carbonyl group into play, which explains its draw for more difficult acylation reactions. Suppliers tend to deliver it in amber glass, tightly sealed and sometimes even under an inert gas blanket, just to keep it from decomposing or reacting with moisture in the air. This stuff earns a spot in labs where high-precision, high-reactivity intermediates stay in demand.
Physical & Chemical Properties
Handling bromoacetyl bromide requires respect for its physical traits. It boils between 111-113°C at atmospheric pressure, and solidifies below room temperature. Its density pushes past 2 g/cm³, and it mixes poorly with water but dissolves easily in non-polar solvents like chloroform and diethyl ether. That hints at the kind of reaction partners it prefers—non-polar substrates thrive, but even trace water ignites violent hydrolysis. This hydrolysis spits out hydrobromic acid and bromoacetic acid vapor, both capable of irritating lungs and eyes in seconds. This kind of reactivity gives the compound its edge, but also drives strict storage and operational rules.
Technical Specifications & Labeling
Regulation insists on clear labeling for bromoacetyl bromide. Any reputable supplier provides purity, batch number, lot analysis, and recommended shelf life right on the bottle. The CAS number is always present, and thanks to several regulatory lists, hazard pictograms cover flammability, toxicity, and environmental risk. Technical specs often include IR and NMR fingerprint data, plus moisture content and stability notes. From my own lab work, seeing a bottle marked “Protect from light and moisture; keep tightly closed in a dry, cool environment” carries just as much weight as the chemical formula printed next to the hazard diamonds.
Preparation Method
For decades, most chemists have generated bromoacetyl bromide from the reaction of bromoacetic acid with phosphorus tribromide or thionyl bromide. Adding the acid to the halogenating agent under cold, dry conditions generates strong fumes, so the setup demands strong ventilation and glassware able to handle corrosive byproducts. After the reaction finishes, distillation removes unwanted reactants and byproducts, usually under reduced pressure to lower the risk of thermal runaway. Adjusting the process can swing the yield and purity, meaning the best labs watch temperature, reagent ratio, and equipment cleanliness to avoid dangerous decomposition or formation of unwanted tars.
Chemical Reactions & Modifications
Bromoacetyl bromide thrives as an acylating agent. It attaches the bromoacetyl group to amines, alcohols, and even some aromatic rings. Once attached, that bromo atom acts as a handle for additional transformation—substitution with azide, displacement with thiol, or opening up more complex ring systems for medicinal or agricultural chemistry. Many antibiotics, herbicides, and enzyme inhibitors find their origins in a reaction with bromoacetyl bromide. Chemists working with this molecule learn to control the reaction’s exothermic kickback, often cooling their flasks and planning for fast workup to avoid dangerous fuming or equipment damage.
Synonyms & Product Names
Chemists know bromoacetyl bromide by several names. Some call it Acetyl Bromide, Bromo-; others stick to Bromoacetic acid bromide; more technical catalogs prefer Bromoacetylbromid or 2-Bromoacetyl bromide. Whether you read through German catalogs or American safety sheets, the CAS number 598-21-0 keeps everyone on the same page. Real-world use involves careful communication, since shipping or ordering the wrong halide can set a project back by days.
Safety & Operational Standards
Bromoacetyl bromide takes a heavy hand when it comes to safety. Even trace inhalation of the fumes provokes coughing, burning eyes, and in some cases, delayed pulmonary edema. As a practicing chemist, I always worked in a certified fume hood, double-gloved with heavy nitrile and safety goggles. Emergency showers and eyewash stations stay non-negotiable, since a drip on exposed skin blisters rapidly and contaminates air with acidic vapor. Waste gets neutralized in a controlled fashion using sodium thiosulfate and water, but only after checking ventilation and keeping spill kits close. Over the years, several incidents have proven that even vigilant workers fall victim to lapses, which is why the best labs use small quantities and demand documented training before anyone opens a bottle.
Application Area
Few chemicals shape the backbone of modern pesticides and pharmaceuticals like bromoacetyl bromide. Agrochemical companies rely on it to create new herbicide backbones resistant to metabolic breakdown in plants. Pharma teams use it as a starting point for beta-lactam antibiotics, antiepileptics, and cancer drugs, exploiting the molecule’s acylating strength and bromo-leaving group. Even in peptide research, bromoacetyl bromide appears as a tool to install bromoacetyl handles for fluorescent labeling or crosslinking studies. Anyone in academia working with protein modification or small-molecule drug discovery has probably wrestled with its fuming bottle at least once.
Research & Development
R&D teams track changing regulations and look for greener pathways to halogenated intermediates like bromoacetyl bromide. The harsh reagents used in its synthesis, paired with environmental pressure to reduce halogen waste, drive research into catalytic and electrochemical substitutions. One promising approach swaps in less volatile brominating agents, which helps control the rapid onset of hazardous fumes. Another stream of research explores immobilized reagents or microfluidic reactors, cutting risk and improving the reproducibility of scaled production. The momentum of biological and medicinal research keeps fueling demand, pushing scientists to think smarter about how to use and reuse every gram they handle.
Toxicity Research
Studies on bromoacetyl bromide’s impact point to acute lung toxicity, skin necrosis, and severe environmental harm. Rodent studies reveal that even low-dose inhalation triggers measurable loss of lung function and persistent tissue damage. The hydrobromic acid byproduct causes additional irritation, forcing labs to implement strict waste controls and rapid neutralization routines. Over the years, occupational health records have logged several near-misses and minor exposures, confirming the need for constant PPE and engineered safety controls. Manufacturers and research firms alike check regulatory updates monthly, since government agencies tighten controls in step with new findings.
Future Prospects
Bromoacetyl bromide has carved out a niche that won’t disappear soon, but mounting pressure for safer, more sustainable reagents sits right around the corner. Next-generation synthesis platforms, perhaps involving photochemistry or biocatalysis, hold promise for cutting out the traditional reliance on hazardous bromine sources. Young chemists starting out now receive more training in green chemistry and risk assessment, and this new generation shows less tolerance for avoidable hazards. To keep its foothold, bromoacetyl bromide’s production and handling will adapt, finding balance between reactivity and safety. As more industries raise the bar for environmental stewardship and worker safety, the labs that call themselves leaders will look beyond tradition for answers, driving new research and smarter use of one of chemistry’s more challenging reagents.
Opening the Laboratory Door
Bromoacetyl bromide lands on the bench in a small brown bottle. It smells harsh, catches in the throat, and wears a warning label for a reason. I remember my own time in the university synthesis lab, the tang in the air persistent every time someone opened a fresh ampoule. Long lab coats, gloves, careful movements—nothing about this chemical ever felt casual. It sits in the toolkit for organic synthesis, not something most households will ever worry about, but its fingerprints turn up across the chemical industry.
The Workhorse of Synthesis
Inside organic chemistry labs, bromoacetyl bromide carries special weight for building more complex molecules. Pharmaceutical companies and research groups count on it to make intermediates. Drop it into a reaction, and it swaps out simple atoms for a bromoacetyl group, like upgrading car parts to build a race car. It’s especially useful in producing peptides, certain antibiotics, and protective groups for amino acids. Without reagents like this, much of modern drug discovery would grind to a halt.
How Bromoacetyl Bromide Earns Its Keep
This reagent lets chemists customize molecules quickly. If a scientist aims for a new cancer medicine or pesticide, running into a dead end, bromoacetyl bromide sometimes opens a new path. Its strength comes from a dramatic story at the molecular level. It reacts fast and with purpose, swapping out hydrogen with a bromoacetyl group and saying, “Your molecule isn’t done yet—now you can add more.” Plenty of patents name it as a key ingredient in producing enzyme inhibitors. Research points to its essential part in the synthesis of local anesthetics and special dyes, produced in volumes big enough to keep suppliers on their toes. In biotechnology, attaching fluorescent molecules to DNA can depend on using bromoacetyl bromide as a starting scaffold.
Risks That Travel Beyond the Lab
The dark side of such power lies in its danger to health and the environment. Forget eye protection, and you might learn about its corrosive bite the hard way. Inhalation can damage the lungs, and skin contact brings immediate burns. That alone urges for heavy training before using it. Production and handling keep specialist companies on alert. Once, in a smaller facility I visited, every transfer happened in a glove box, and spills meant lockdowns rather than quick cleanups. Regulations around the world follow this reality: Bromoacetyl bromide counts as a hazardous substance and stirs special shipping restrictions.
Safety and Looking Forward
Could science do without it? That’s still under debate. For projects demanding precision tools, bromoacetyl bromide fills a niche tough to replace. Some university labs have begun to search for less hazardous alternatives or at least greener methods for using and disposing of irritants like this one. Green chemistry seeks newer, safer building blocks and better protections for workers. Companies can invest in enclosed transfer systems, improved fumigation, and rigorous training. Those steps might look expensive up front, but they spare headaches—and sometimes lives—down the road.
Bromoacetyl bromide keeps a low public profile, but chemists know its significance. Balancing progress in synthetic chemistry with the safety challenges shows the bigger story playing out in every research lab: the need to respect the tools that push science forward.
Why Working with Bromoacetyl Bromide Raises Red Flags
Stepping into a lab for the first time and seeing a bottle labeled “bromoacetyl bromide” would make anyone pause. This chemical doesn’t get handled like table salt in a kitchen. With two reactive bromine atoms attached to an acyl group, bromoacetyl bromide belongs to a group of chemicals that turn serious the moment a bottle cap comes loose. Inhaling even a small whiff can hammer your lungs. I learned early on that rushing through safety habits with chemicals like this is a shortcut to the emergency room.
Personal Protective Equipment: The Front Line
I remember a training where an older chemist told us stories about gloveless hands and ruined careers. Handling bromoacetyl bromide, I’ve never skipped on thick nitrile gloves, a proper lab coat, and splash-proof goggles. Not safety glasses, but goggles with a side and bottom seal. This isn’t overkill—it’s basic defense. A single splash on skin or eyes burns for days and leaves scars. Avoiding open-toed shoes, and sometimes even wearing a face shield for overhead work, keeps the margin for error slim.
Fume Hood: Not Just a Suggestion
The sharp, acrid odor of this compound hints at the risk. Only handling bromoacetyl bromide in a properly working fume hood keeps those toxic vapors out of your lungs. Hood sashes should stay low, arms under the sash line, never leaning close. One researcher I knew ignored this, and he ended up on oxygen support that day. The vapor isn’t just an irritant; it chews up tissue before most people realize what’s happened.
Storage and Spill Preparedness
Sealed glass bottles stored in ventilated, cool cabinets marked with hazard labels keep everyone in the lab out of danger. Never use plastic, because even some thick plastics don’t stand up to bromoacetyl bromide. Clear labeling and regular checks for leaks or degraded bottle caps matter more than most realize.
Spills demand directed action. I keep a spill kit nearby stocked with sodium bicarbonate, sand, absorbent pads, and a sturdy container. Plenty of people freeze up or try to mop up dangerous chemicals with paper towels. That just spreads disaster. Team training and clear instructions mean someone can act fast without calling a supervisor during a real emergency.
Fire Risk and Emergency Protocols
Bromoacetyl bromide reacts violently with water, so having a standard water-based extinguisher doesn’t help—dry chemical extinguishers stand ready near storage and workstations. Knowing where the safety showers and eyewash stations sit is basic, but too many labs treat it like trivia. Drills aren’t a box-ticking exercise. Over the years, I’ve seen that teams who take drills seriously prevent injury when something goes wrong.
The Cost of Overlooking the Basics
Many accidents with chemicals like bromoacetyl bromide stem from complacency—rushing a procedure, skipping a double-check, storing next to an incompatible chemical. Root cause comes back to habits. Following safety data sheets, working methodically, and sharing warnings with newer team members aren’t just formalities. Labs can get complacent, especially when everyone’s pressed for time or tired after a long day. Building a culture where people speak up about safety—and act on it—means fewer close calls and more careers with all limbs and senses intact.
Why Extra Care Matters with This Reagent
Bromoacetyl bromide stands out as a reagent with a notorious sting. I remember the first time I came across it during my early research days. Even now, the sharp, pungent odor comes back to me. The real reason careful storage matters with compounds like this is simple: health and safety. Years of field experience taught me that one cracked cap, or one unsealed container, endangers not just the chemical but the people nearby.
Understanding Its Hazards
This substance is aggressive on contact—skin, eyes, airways, and equipment all face immediate threats if things go wrong. The fumes alone cause irritation or worse. A quick scan of the CDC’s chemical safety summaries makes it clear: exposure can lead to coughing, burning, or severe lung damage. Spills rapidly spiral into emergencies. With records of fires and violent reactions, you don’t cut corners just because a bottle sits quietly on the shelf.
The Value of Dry, Cool, and Airtight Storage
Years spent in academic and industrial labs showed the importance of more than just stashing reagents on any free shelf space. Bromoacetyl bromide reacts with water and humid air, which means moisture ruins purity and risks pressure build-up. Heat accelerates decomposition, producing toxic gases. Any chemist with real-world bench experience recognizes the signs: warped containers and that unmistakable sweet-acidic smell hint at chemical breakdown. Storing it far from light and heat—locked up in a ventilated chemical refrigerator—makes the difference between safe use and hazardous mistakes.
Compatible Containers and Secure Facilities
I’ve learned stainless steel and high-grade glass work best for containment. Cheaper plastics or makeshift lids absorb fumes and soon crack or warp. You want a cap that’s solid and leakproof—no improvisation. The best labs have purpose-built acid cabinets, double-sealed and well-marked, tucked away from general traffic. Access goes only to trained personnel. Records show that accidental mixing, especially with amines, alcohols, or water, can result in explosions or dangerous smoke. That's not theory—lab safety audits often trace close calls right back to a rushed storage decision or a mislabeled bottle shoved out of the way.
Routine Checks and Staff Training Reduce Incidents
Experience taught me that even the right cabinet and bottle don’t matter if people aren’t diligent. I check seals, labeling, and log storage dates—a few minutes every month spare big headaches later. The teams I’ve seen fare best run safety drills, refresh spill response plans, and limit who handles anything volatile. Could things still go wrong? Human error never goes away entirely. A culture of respect for procedures always trumps reminders pasted on the wall.
Modern Tracking and Emergency Readiness
With digital inventory systems, it’s now easier to know what you have and where you keep it. These tools cut down on lost bottles and outdated stock. Emergency neutralizers—sodium carbonate and activated charcoal—sit near the storage zones for fast response. I still recall an incident at a university lab—one whiff was enough for the team to recognize a bad seal. Shared vigilance, not just personal memory, lets everyone react quickly and reduce drama.
If you’ve handled bromoacetyl bromide, the lesson sticks: proper storage isn’t paperwork, it’s the first step in protecting health, research, and the reputation of any lab. Ignoring best practices invites accidents and sleepless nights.
Anatomy of Bromoacetyl Bromide
Bromoacetyl bromide’s formula looks simple at first—C2H2Br2O. Behind those letters lies a molecule with plenty of stories. Think of it as a carbon backbone with a bromine atom at both ends, bookending a reactive core. Plenty of chemistry textbooks spell it out: it’s a derivative of acetic acid, where the methyl group wears bromine instead of hydrogen, and acyl chloride comes swapped for bromine too. In structure, a central carbon links directly to a bromine (Br), a carbonyl (C=O), and a bromomethyl group. Mapping it out, you’d stagger the bromines at opposite poles of the two-carbon chain, staring back at each other across a short stretch. Chemists like drawing it as BrCH2COBr.
Living With Its Reactivity
You don’t cross paths with bromoacetyl bromide without respecting its volatility. It’s not friendly to skin, eyes, or lungs. My first encounter with it in a university lab set off the building’s alarms. The compound releases strong fumes, and reacting with water generates hydrobromic acid. One story that sticks in my mind—an accident involving a broken vial landing on wet benchtop. The white vapor sent students scrambling for safety. This stuff does serious harm, and its reactive nature serves as a reminder: chemistry demands vigilance.
Why Chemists Chase Bromoacetyl Bromide
It’s prized for making other complex chemicals. Pharmaceutical labs use it for making certain drugs via acylation, where it drops its bromoacetyl group onto other molecules. Organic synthesis often borrows its punch to build blocks for more advanced molecules. The bromine atoms, sitting like flags on the molecule, make it easier to swap in other groups. A personal favorite application—making intermediates for local anesthetics. Researchers often face hurdles trying to replace its use with safer options, but nothing matches its straightforward reactivity.
Safety and Environmental Impact
The hazards don’t stop at toxicity. Spills can result in fumes that threaten both workers and the neighborhood. Bromoacetyl bromide requires thick gloves, splash shields, and a fume hood. Any time it escapes into the environment, it ends up in the atmosphere or waterways as acidic byproducts. Agencies like OSHA and the EPA keep a close eye on its handling. Some labs now try switching to less aggressive reagents. I also remember a colleague lobbying for automated dispensing to protect staff. Progress arrives slow, pressured by both the utility of this molecule and the risks that come with it.
Balancing Progress and Precaution
The need for bromoacetyl bromide won’t dry up soon. Its efficiency in synthesis means researchers will keep coming back to it. Some manufacturers now invest in storage and material transfer systems designed for high risk. Meanwhile, green chemistry research continues hunting for gentler replacements—work that could mean fewer alarms and safer benches for students. For those working with this compound, education and vigilance prove just as important as the molecule itself.
What Makes Bromoacetyl Bromide Dangerous?
Bromoacetyl bromide serves a purpose in chemical synthesis, but its hazards far outweigh its convenience for anyone not working inside a chemical lab. This stuff hits the body hard—fast. It irritates skin, eyes, throat, and lungs, and even small splashes or inhaled vapors trigger burning pain, redness, and coughing.
This isn’t the kind of chemical you’d want to even accidentally bump into. It releases corrosive gases that can damage the mucous membranes, making the simple act of breathing a risk. Some people might not realize how offensive the smell or sting could be until they're already in trouble. If someone ignores the warning signs or doesn’t have protective gear, exposure can lead to real health emergencies—think severe eye damage, blistered skin, or dangerous swelling in the throat making breathing tough.
What Happens to People Exposed?
Speak with anyone who's experienced a lab accident, and there’s a clear message: fast action makes a difference. Bromoacetyl bromide causes immediate discomfort, from watery eyes and chest tightness to rapid burning or blistering on exposed skin. Swallowing the stuff is out of the question—it damages the digestive tract and can quickly turn into a life-threatening situation.
Accidents get worse once the chemical reaches the eyes or gets inhaled. Permanent vision loss can result without quick flushing. Inhaling vapors could lead to throat closure or lung injury, which means someone might lose consciousness or stop breathing if nothing is done in time. I remember reading accounts from chemists who shared stories about colleagues being rushed to the emergency room because a few minutes’ delay nearly cost their eyesight or lungs.
First Aid: Quick Steps Matter
Working around bromoacetyl bromide means knowing what to do—and not waiting to act. If a spill lands on skin, the response is to strip off all affected clothing and wash the area under running water for at least 15 minutes. No "just wipe it off" or "wait it out"; water, lots of it, is the only answer until a doctor can see you.
Splashes in the eye call for the eyewash station, not a wet towel or your own hands. Hold lids open and flush eyes for a solid 15 minutes. Don’t rub—rubbing burns in the chemical even deeper. If breathing problems start, it's crucial to get out of the room right away and into fresh air, then emergency medical care is next. Don’t tough it out—lung and throat swelling gets worse by the minute and home remedies offer no help.
Swallowing isn’t likely for most, but lab mistakes happen. Don’t try to throw up, and forget the water glass—just get medical help as fast as possible. Doctors know how to handle the damage to internal organs much better than anyone at the scene.
What Prevents These Accidents?
In my experience, nothing beats training and double-checking safety gear before opening a single bottle of bromoacetyl bromide. Gloves, goggles, face shields, and lab coats make all the difference between a safe experiment and a trip to the emergency department. Fume hoods aren’t just for show—they’re a line of protection when dealing with fumes that can scar tissues in a single breath.
Labs that have firm safety cultures—clear procedures, routine drills, no shortcuts—see fewer incidents. The right mindset among workers, especially new students, does more than any warning sign. Hazardous chemicals demand respect, and real stories about accidents ripple through a lab community, making the risks vivid and reminding people not to get complacent.
| Names | |
| Preferred IUPAC name | 2-bromoacetyl bromide |
| Other names |
Acetyl bromide, bromo-
Bromoacetic acid bromide Bromoacetyl bromide Bromacetylbromid Bromoacetyl dibromide |
| Pronunciation | /ˌbroʊ.moʊ.əˈsiː.tɪl ˈbroʊ.maɪd/ |
| Identifiers | |
| CAS Number | 1519-30-8 |
| Beilstein Reference | 3596801 |
| ChEBI | CHEBI:51101 |
| ChEMBL | CHEMBL1377 |
| ChemSpider | 10146 |
| DrugBank | DB08761 |
| ECHA InfoCard | 100.019.739 |
| EC Number | 205-855-4 |
| Gmelin Reference | 10508 |
| KEGG | C19205 |
| MeSH | D001957 |
| PubChem CID | 65341 |
| RTECS number | AG8925000 |
| UNII | 732X27FZ1I |
| UN number | UN1737 |
| CompTox Dashboard (EPA) | DJ7PAU888M |
| Properties | |
| Chemical formula | C2H2Br2O |
| Molar mass | 230.82 g/mol |
| Appearance | Colorless to light yellow liquid |
| Odor | Pungent |
| Density | 1.977 g/mL at 25 °C |
| Solubility in water | Decomposes |
| log P | 1.68 |
| Vapor pressure | 3 mmHg (20°C) |
| Acidity (pKa) | -8.2 |
| Magnetic susceptibility (χ) | -7.36 × 10⁻⁶ cm³/mol |
| Refractive index (nD) | nD 1.527 |
| Viscosity | 3.109 cP (20°C) |
| Dipole moment | 2.60 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 285.9 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | −215.7 kJ·mol⁻¹ |
| Std enthalpy of combustion (ΔcH⦵298) | -473.7 kJ/mol |
| Hazards | |
| Main hazards | Toxic if swallowed, inhaled or in contact with skin; causes severe burns and eye damage; may cause respiratory irritation; reacts violently with water. |
| GHS labelling | GHS02, GHS05, GHS06 |
| Pictograms | GHS05,GHS06 |
| Signal word | Danger |
| Hazard statements | H301 + H311 + H331, H314, H330 |
| Precautionary statements | P210, P260, P261, P264, P271, P280, P301+P330+P331, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P370+P378, P403+P233, P405, P501 |
| NFPA 704 (fire diamond) | 3-2-2-W |
| Flash point | Flash point: 43°F (6°C) |
| Autoignition temperature | 170 °C |
| Lethal dose or concentration | LD50 (oral, rat): 640 mg/kg |
| LD50 (median dose) | LD50 (median dose): 75 mg/kg (rat, oral) |
| NIOSH | AC4025000 |
| PEL (Permissible) | PEL: 1 ppm (5 mg/m³) |
| REL (Recommended) | 25-35°C |
| IDLH (Immediate danger) | 50 ppm |
| Related compounds | |
| Related compounds |
Acetyl bromide
Chloroacetyl chloride Bromoacetic acid Bromoacetyl chloride |
