Ethyl Bromoacetate: A Practical Look from History to Modern Lab Bench
Historical Development
Ethyl bromoacetate first showed up in chemistry texts during the late nineteenth century. Early chemists in Europe, tinkering with various synthetic routes, found that swapping different elements onto simple molecules created a wave of new reagents. Once production of ethyl bromoacetate became reliable, research groups started using it for synthetic routes in the rapidly growing field of organic chemistry. This clear, colorless liquid soon became a staple in academic and industrial labs, with applications evolving alongside the bigger picture of industrial growth and expanding chemical manufacturing.
Product Overview
Ethyl bromoacetate serves as a handy building block in chemical synthesis. It contains a bromo group and an ester, two reactive sites that let chemists perform a huge variety of transformations. Bottles of this chemical line the shelves in universities, contract research organizations, and pharmaceutical facilities. If you’ve watched someone work with it, you’ll recognize the sharp, pungent odor that comes from its volatility. Folks rely on its reactivity for both small molecule drug work and material science projects.
Physical & Chemical Properties
Ethyl bromoacetate looks like a typical colorless liquid. It has a distinct, almost biting odor, a boiling point near 158°C, and a density just above that of water at about 1.5 g/mL. Its molecular formula is C4H7BrO2, giving it a molar mass close to 167 g/mol. What sets it apart is the polar ester and the highly reactive carbon adjacent to the bromine. It dissolves best in organic solvents, and the volatility demands careful ventilation in the lab. Exposure to air for too long sends vapors wafting throughout the workspace, and accidental spills can linger in the nose for hours.
Technical Specifications & Labeling
You’ll find commercial ethyl bromoacetate labeled with purity, water content, and key hazards. The most common assay runs above 98%, fitting most synthesis needs. Suppliers have to spell out the product’s hazards under GHS rules. Labels warn about flammability, acute toxicity, and risk of skin burns. That red diamond pictogram tells even the most seasoned chemist to grab the right gloves and goggles before cracking open the container. Transport follows guidelines for hazardous chemicals, typically as a flammable, toxic liquid. Safety Data Sheets provide all the needed details for safe handling and emergency cleanup.
Preparation Method
In any undergraduate lab, someone has probably tried making ethyl bromoacetate by reacting bromoacetyl bromide with ethanol in the presence of a base. The classic method uses bromoacetic acid and ethanol, with acid catalysis driving the esterification. Large-scale facilities favor continuous reactors for steady, safe control over the exothermic steps. I’ve watched a bench chemist carefully measure out reagents, mindful of every drop to avoid excess bromoacetic acid that can make workups miserable. Washing and drying bring the product to an acceptable lab quality, sometimes followed by distillation for high-purity needs.
Chemical Reactions & Modifications
Ethyl bromoacetate plays well in alkylation and nucleophilic substitution reactions. Chemists count on its bromo group for SN2 attacks by carbanions, amines, and thiols. It’s the go-to reagent in making α-amino acids, and without it, many amino acid syntheses would crawl instead of sprint. The ester group can undergo hydrolysis or be swapped for others through transesterification. Some research teams apply it in preparing intermediates for pharmaceuticals and agrochemicals, using its structure to plug reactive fragments into more complex molecules. There’s almost a pride in seeing a messy reaction mixture yield beautiful crystals of some new α-bromo ester.
Synonyms & Product Names
Few chemicals wear as many names as ethyl bromoacetate. The core identifiers—ethyl 2-bromoacetate, 2-bromoacetic acid ethyl ester—show up in catalogs and academic literature. Some manufacturers settle on shortened product codes or proprietary names, but every chemist recognizes the blue streak on the label and the unmistakable aroma in the workroom. There’s a sort of underground language among seasoned lab folk for naming it, with a few grins about avoiding confusion during late nights of column chromatography.
Safety & Operational Standards
Nobody should treat ethyl bromoacetate like vinegar. Toxicity ranks high, capable of causing skin burns and eye damage, and even inhalation can spark respiratory issues. Standard PPE—nitrile gloves, lab coat, goggles—protects against splashes, but spills require quick thinking and plenty of ventilation. Facilities store it in flammable liquid cabinets, segregated from acids and oxidizers. Training covers handling, spill response, and how to use emergency eyewash stations. My own rule: never work with it on an empty stomach or when feeling rushed, since carelessness leads straight to trouble.
Application Area
Ethyl bromoacetate forms a backbone in synthetic organic chemistry. Medicinal chemistry teams use it to create amino acid derivatives, key fragments in peptide synthesis, and specialized agents for complex natural product projects. Agrochemical development relies on it when building certain herbicide or fungicide scaffolds. Material science finds uses for it in surface modification reactions, setting up the introduction of functional groups on polymers or specialty coatings. You can walk into any serious synthetic lab and spot a graduate student shaking a flask that almost certainly contains a few drops of this stuff. Its reliability means chemists come back to it, year after year, project after project.
Research & Development
Academic research still drives plenty of new chemistry using ethyl bromoacetate. Graduate students develop routes for heterocycles, bioactive molecules, and enzyme inhibitors. Some pharmaceutical companies have invested in automating synthetic workflows that start with this molecule, looking to speed up drug discovery. Specialty manufacturers keep tweaking processes to make production greener, with less waste and smaller energy footprints—a growing concern as regulatory pressure mounts. I’ve seen a few projects stall out until someone reached for a bottle of ethyl bromoacetate, and with one careful reaction, everything clicked back into motion.
Toxicity Research
Toxicologists flagged ethyl bromoacetate as hazardous decades ago. Inhaled or absorbed through skin, it causes irritation and, at higher doses, more severe symptoms. Animal studies showed impacts on liver and nervous system function when doses run high. Recent work focuses on identifying the exact breakdown products in living systems, as researchers want to better predict occupational hazards. Regulations now require proper disposal, with waste handled as halogenated solvent streams, not just dumped down the drain. Safety committees publish periodic updates, keeping the data fresh for labs across the world.
Future Prospects
The outlook for ethyl bromoacetate ties closely to the growth of green chemistry and automation. Engineers and process chemists develop new catalytic methods that either avoid hazardous halogenated reagents or recover them with less waste. Artificial intelligence nudges its way into reaction optimization, streamlining syntheses that still rely on key bromoesters as starting points. Market demand continues, but expectations shift toward safer, sustainable, and cost-effective manufacturing. I hear more conversations about closed-system handling, preventing both environmental release and worker exposure. For as long as synthetic chemistry matters, ethyl bromoacetate will keep earning a place in labs worldwide, a chemical with a messy past and plenty of potential ahead.
From Laboratory Bench to Factory Floor
Ethyl bromoacetate looks like another chemical name best left to scientists, but its reach goes well beyond a shelf in a research lab. It shows up in the hands of folks working on real-world problems—a quiet player in medicine, industrial chemistry, and beyond. Many have never heard of it, yet it’s stitched into the story of modern chemistry.
Chemistry’s Swiss Army Knife
I remember seeing bottles of ethyl bromoacetate labeled boldly in my university’s organic prep lab. Researchers valued it for its reactivity. Add it to the right mix, and suddenly you can build molecules that treat diseases or help crops grow. Ethyl bromoacetate makes an excellent source of the “bromoacetyl” group, which attaches easily to many starting materials. That flexibility has made it a go-to choice for those trying to link together the building blocks of life—like amino acids and peptides.
It pops up in textbooks every year, often as a simple “alkylating agent.” Basically, it helps stick one carbon chain onto another. This small trick finds a role in making cancer drugs, local anesthetics, and even complex pesticides. Its power lies in how efficiently it can add a carbon “handle” to molecules, letting chemists shape substances for the needs of medicine or agriculture.
Inside the World of Pharmaceutical Synthesis
Drug makers often need shortcuts to batch-produce lifesaving compounds. Ethyl bromoacetate plays the quiet workhorse here, especially in the early stages of medicine development. For example, in the creation of benzocaine—a local anesthetic commonly used by dentists—ethyl bromoacetate lays the foundation. Without it, companies would need longer steps or more expensive starting materials.
Its reach doesn’t stop there. Chemists turn to it when creating certain amino acid derivatives and peptidomimetics, which imitate protein fragments. These specialized compounds help in designing experimental drugs for diseases ranging from bacteria to cancer. Ethyl bromoacetate’s presence streamlines these processes, which can shave months off complicated syntheses.
Industrial and Agricultural Impact
On the agricultural side, ethyl bromoacetate helps in crafting some important crop protection agents. For example, some herbicides rely on the unique chemistry it provides. Its impact shows up in fields thousands of miles from any laboratory, woven into modern food systems.
In industry, this reagent makes its way into dyes and flavors, often as a starting ingredient for more elaborate compounds. It takes skilled hands to manage, since it can cause burns and needs careful storage. Still, manufacturers in pharmaceuticals, dyes, and specialty chemicals choose it for the sheer versatility it offers.
Safety Concerns and Smarter Solutions
Ethyl bromoacetate isn’t something to handle lightly. Even as a trained professional, I needed gloves, fume hoods, and a good respect for its risks. Exposure can lead to breathing troubles or serious skin irritation. This points to a larger issue: the chemical industry keeps moving, seeking safer alternatives where possible. Some newer reagents offer similar benefits with fewer hazards, but the old standby stays on the shelf because of reliability and cost.
Looking Ahead
What’s needed: better handling education, investment in safer chemical alternatives, and support for researchers pursuing greener routes. Safer processes don’t just protect chemistry students or workers. They ripple out, raising standards for the whole supply chain—from the factory to the food on the table or the pills in a medicine cabinet.
No single molecule has all the answers, but compounds like ethyl bromoacetate show how everyday science rides on careful choices and steady hands.
Recognizing the Hazards Upfront
Ethyl bromoacetate shows up in organic chemistry labs, known for helping in making flavors, medicines, and dyes. I remember my first time opening a bottle—the sharp, irritating smell was enough to make me double-check if my goggles fit tightly. Its strong odor isn’t just unpleasant. It means danger. This stuff can damage eyes, burn skin, and cause long-term breathing trouble if you get careless. Many students skip reading labels or safety sheets, trusting their usual lab routine. That’s a risk that catches up fast. Ethyl bromoacetate soaks through gloves and skin before you know it. Even a splash or fume exposure can leave you sore and coughing.
Personal Protective Equipment: Your Best Bet
The first rule: don’t touch the bottle unless you have proper gloves—nitrile or butyl rubber, not standard latex. Lab coats and splash-proof goggles go on before you open a bottle. One day, I rolled up my sleeves during a warm afternoon, thinking short sleeves would keep me cool. I brushed a drop on my wrist and felt irritation set in within minutes. Never trust bare skin near this chemical. A good set of gloves and a reliable face shield or goggles guard against splashes and unpredictable spills. Put them on as if your safety depends on it, because it does.
Protecting Your Lungs and Avoiding Fumes
Ethyl bromoacetate isn’t just a contact risk. Breathing the vapor can hurt your lungs and nervous system. Use a fume hood every time, no excuses. A busy lab might make it tempting to just “grab and mix” at the bench, but any shortcut can cost you your health. I’ve seen too many cases of sneezing and burning sinuses, all preventable by taking an extra step to use the hood. Make sure the sash is as low as possible, with hands and chemicals kept inside the airflow.
Good Storage Habits Save Lives
After working with ethyl bromoacetate, never leave it on a shared bench. The chemical gets into the air and onto surfaces without warning. Seal containers tightly and label them clearly. Store away from heat and sunlight in a chemical cabinet made for organics and toxics. A lab mate once left a flask out after an experiment, forgetting the fumes would creep into the whole room. The clean-up took hours, and headaches lasted longer. Secure storage is as important as safe handling.
Unexpected Spills and Emergency Steps
Despite best intentions, accidents can happen. Know exactly where to find the eyewash station and safety shower. In one case, I watched someone freeze after a glass tube broke—hesitation just made things worse. Grab the spill kit, soak up liquid with absorbent pads, and throw away any contaminated gear in the hazardous waste. Never try to mop spills with regular towels. Call for backup if you get splashed or breathe in fumes; don’t tough it out or hope symptoms pass.
Solutions: Training and Mindset
Chemistry is unforgiving about shortcuts. Keep training current and stay sharp about the latest guidelines. Pair new lab workers with experienced team members for practical demonstrations. Emphasize that safety checks are as routine as weighing reactants. Up-to-date material safety data sheets must be close at hand, and regular safety drills prepare everyone for real mistakes. Behind every rule lies a real story about someone who tried luck with chemicals and paid for it.
Getting to Know Ethyl Bromoacetate
Ethyl bromoacetate has a chemical formula of C4H7BrO2. At first glance, that might look like a tangle of letters and numbers, but that formula lays out the real story of what’s inside each molecule: four carbons, seven hydrogens, one bromine, and two oxygens. This simplicity doesn’t stop the molecule from playing its own interesting role in both lab benches and chemical industries.
Opening Up the Structure
This molecule begins with an ethyl group (CH3CH2-) attached to an oxygen. This oxygen links up, ester-style, with a bromoacetic acid fragment. So, if you sketch it, the structure rolls out as BrCH2COOCH2CH3. The bromine sits at the far end of the chain, attached to a carbon that’s further joined to the carbonyl and then to the oxygen holding the ethyl group. Looking at it in three dimensions, the bromo-acetate chunk brings the chemical punch, while the ethyl group dials up solubility and reactivity.
Where It Shows Up and Why It Counts
Ethyl bromoacetate’s real draw comes from how it reacts with other compounds. It’s not something people bump into on grocery shelves, but research chemists—including folks on my university bench—pull it out whenever they need to build something new. Its value comes from that bromine; this atom doesn’t like to hold onto the carbon too tightly, which makes reactions easier to run. Swapping in a new group or stretching a carbon chain suddenly becomes a whole lot simpler.
I’ve watched it change the course of a project myself. Trying to piece together a tricky ring system for an undergraduate research project, ethyl bromoacetate let us stitch together a chain through nucleophilic substitution, an old-school but reliable move. The results didn’t just show off good yields; they proved the molecule can create new bonds that never existed before. That flexibility turns ethyl bromoacetate into a bit of a Swiss Army knife for organic chemists, especially for making new drugs, dyes, or specialty chemicals.
Risks on the Bench
The same chemistry that makes ethyl bromoacetate useful comes with some real risk. Bromine compounds demand respect, and this one sticks to that trend. Breathing it in can lead to a cough that hangs around, headaches, and a sore throat. Skin contact won’t go unnoticed either—it burns and irritates. Nobody in my lab touched the stuff without a fume hood and thick gloves. Responsible handling doesn’t just follow a rulebook; it protects anyone close by from some harsh surprises.
Working Toward Safer Chemistry
Safer practices come from repeated habit, smart storage, and substitution where possible. Some newer labs look for alternatives or work with smaller batches to limit risk. Manufacturers put tighter controls in place as more data comes out, and that leads to better training and awareness across the board. People in charge of teaching or workplace safety can cut incident rates just by sharing their own stories—mistakes and all. Simple adjustments, like using proper ventilation or prepping neutralizing agents, create safer spaces without sacrificing the progress that molecules like ethyl bromoacetate make possible.
Supporting the Future
Research communities always weigh the benefits and hazards of compounds like ethyl bromoacetate. This molecule’s structure, its formula, and the risks it packs remind everyone that chemistry pulls together curiosity and responsibility. Watching the practical side up close, the lessons run deeper than textbooks alone can offer.
Understanding the Substance
Ethyl bromoacetate shows up in many organic chemistry labs thanks to its use as an alkylating agent. With a low boiling point and a tendency for volatility, it doesn’t play well with water, strong bases, or open air. The vapor irritates the eyes and lungs, and even a small spill spreads a strong, unpleasant odor through the work area. So, this isn’t the type of bottle anyone leaves on a regular benchtop.
Choosing the Right Storage Spot
Lab safety rules don’t exist just to fill up the pages of a manual. Over the years, I’ve seen firsthand what neglecting these guidelines can bring—leaky storage bottles, fumes, sometimes an impromptu evacuation drill. For a reagent like ethyl bromoacetate, a dedicated flammables safety cabinet is the clear choice. These cabinets slow down flames while a built-in vent helps control fumes. Keeping this chemical cool proves important, so I look for storage areas away from direct sunlight and heat sources. Room temperature in a well-ventilated, climate-controlled lab works fine, as long as temperatures don’t get too hot. Steady conditions keep the liquid stable and limit vapor formation.
Preventing Reactions and Leaks
Ethyl bromoacetate reacts strongly with strong bases, water, or oxidizers. Any spill, even a few drops, can create fumes or even trigger a small reaction. Placing it far away from caustic soda, peroxides, or strong acids prevents headaches and real emergencies. On my own shelves, I keep incompatible supplies at least one compartment away, using clear labeling and separated storage bins.
Choosing the right bottle matters too. Original glass bottles with plastic or Teflon-lined caps do the job best, as the reagent can eat through rubber and ordinary plastics. After sealing, each bottle gets a layer of parafilm and a secondary containment tray—a simple dish or bin—to contain leaks. This habit already saved me from a tough cleanup once, when an old cap started corroding over winter break. I prefer to check bottles now and then for signs of residue, bulging, or discoloration. Anything that looks odd gets flagged for disposal.
Looking Out for the People Around You
Personal protection steps can’t get skipped. Nitrile gloves, goggles, and a long-sleeve lab coat keep skin safe. Working with ethyl bromoacetate right under a fume hood limits exposure. The smell alone will push most people to finish quickly. Good ventilation and air monitoring stop exposure from creeping up over time. I keep the least-used chemicals low, at the back of a shelf, and update my inventory every couple months. These habits stop the buildup of forgotten toxins and old, unstable bottles. If someone else handles storage or cleanup, training should highlight the risks and reinforce these routines.
Improving Practice and Limiting Harm
Experience has taught me that dedicated storage routines pay off in safety and efficiency. Ethyl bromoacetate, though handy, demands respect. Regular checks, careful labeling, strong secondary containment, and clear records limit the chances for leaks, spills, or confusion. In my group, we’ve set up a simple logbook for chemical checks. This move, which only takes a moment, gives people peace of mind and helps meet regulatory guidelines. Good habits like these mean more time on real science, less stress, and a safer workspace for everyone involved.
The Hazards No One Should Brush Aside
Ethyl bromoacetate turns up in labs for making medicines, flavors, and chemical research. Its usefulness comes with a punch—this liquid irritates skin, eyes, and lungs, and the fumes make folks cough or worse if they breathe too much in. Too many stories go untold about near-misses in school labs or chemical storage closets. Folks get a whiff, their eyes burn, and panic hits. That’s why safety isn’t up for debate.
Why Down-the-Drain Doesn't Cut It
Some might wonder why something so simple as pouring leftovers away could become a disaster. Ethyl bromoacetate reacts with water, making hydrobromic acid and other nasties. Once it hits the sink, it doesn’t just vanish. It finds its way to public water or corroded pipes, raising alarms for anyone with a nose for environmental trouble. Workers at treatment plants shouldn’t shoulder risks you send along through careless disposal.
Real Steps For Safe Disposal
You walk through any well-run lab and see lined up safety bottles and fume hoods for a reason. Most labs keep clear glass containers with tight seals, marked for halogenated organics. Safeguarding people starts before any disposal happens—protective gear goes on, windows go open, and fume hoods soak up the vapors. Anyone handling this liquid wears gloves, goggles, and smart folk add a lab coat with fitted sleeves. No shortcuts. The right bottle never holds more than it should, avoiding heat and sunlight. That label tells everyone what’s really inside, which isn’t always the case when bottles get shuffled or old habits sneak in.
Chemical Treatment Beats Wishful Thinking
No one who’s been trained will choose a standard landfill or trash run for ethyl bromoacetate. Chemists handle it through chemical neutralization. One way uses sodium thiosulfate or strong base to break up the harmful parts. These treatments change the structure, making it safer and less reactive. Any leftovers or mix is cooled, labeled, and stored away from acids and heat until professional disposal comes around. Trusting a trained hazardous waste contractor keeps dangerous stuff out of soil and water for good. I’ve seen more than one group think they can handle “small amounts,” only to realize smell or leaks ruin everyone’s day. The lesson sticks—better to call for help than read about an accident later.
Facility Protocols Matter Every Time
Universities, research firms, and chemical suppliers drill this lesson into anyone stepping near ethyl bromoacetate. They're not just following rules—they’re protecting students, janitors, and delivery drivers. OSHA and EPA rules aren’t just paperwork—they’re a shield for people who don’t get a say. I think back on safety seminars where everyone groaned about paperwork, yet no one argues after hearing real stories of accidents from lazy habits. Proper training, clear signage, and fire-ready storage save lives, and that deserves respect.
Stopping Problems Before They Start
Folks keep things safer by buying only what they use quickly, storing leftovers in secure chemical storage with alarms and secondary containment trays. Inventory checks every few months spot leaks before they run wild. Even if it sounds like extra work, that checklist or training video saves trouble every time. Community hazardous waste events, chemical take-back programs, and online experts take out the guesswork for smaller operations or schools. Never letting old chemicals collect dust avoids emergencies later.
Accountability Needs Everyone’s Attention
Safe disposal means more than ticking a box or reading a procedure. It’s a blend of responsibility—care for coworkers, promise to communities, and respect for the environment. I’ve seen chemistry students take serious pride in turning out a safe, clean bench and clear records. It isn’t just habit—it’s knowing their work makes a difference beyond the lab. Every step builds trust and keeps the next headline from being a chemical spill with regrets all around.
| Names | |
| Preferred IUPAC name | Ethyl 2-bromoacetate |
| Other names |
Bromoacetic acid ethyl ester
Ethyl 2-bromoacetate Ethoxycarbonylmethyl bromide Ethyl bromoacetate Bromoacetate ethyl ester |
| Pronunciation | /ˈiːθɪl ˌbroʊmoʊ əˈsiːteɪt/ |
| Identifiers | |
| CAS Number | 105-36-2 |
| Beilstein Reference | 1209227 |
| ChEBI | CHEBI:17608 |
| ChEMBL | CHEMBL141995 |
| ChemSpider | 54684 |
| DrugBank | DB08398 |
| ECHA InfoCard | 01e28c16-11bd-43aa-98ac-13aafd98a3d3 |
| EC Number | 205-490-3 |
| Gmelin Reference | 8575 |
| KEGG | C01756 |
| MeSH | D019325 |
| PubChem CID | 7486 |
| RTECS number | AF9625000 |
| UNII | FDU7TVX1DR |
| UN number | UN1891 |
| Properties | |
| Chemical formula | C4H7BrO2 |
| Molar mass | 167.98 g/mol |
| Appearance | Colorless to light yellow liquid |
| Odor | fruity |
| Density | 1.533 g/mL at 25 °C (lit.) |
| Solubility in water | Slightly soluble |
| log P | 0.97 |
| Vapor pressure | 2.7 mmHg (20°C) |
| Acidity (pKa) | 2.35 |
| Basicity (pKb) | Ethyl Bromoacetate has no significant basicity (pKb) value, as it is not a base. |
| Magnetic susceptibility (χ) | -48.5 × 10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.434 |
| Viscosity | 1.826 cP (20°C) |
| Dipole moment | 2.20 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 354.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -398.75 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -699.7 kJ/mol |
| Pharmacology | |
| ATC code | '' |
| Hazards | |
| GHS labelling | GHS02, GHS06 |
| Pictograms | GHS02,GHS06 |
| Signal word | Danger |
| Hazard statements | H302, H312, H315, H319, H332, H335 |
| Precautionary statements | P210, P261, P280, P301+P312, P305+P351+P338, P405, P501 |
| NFPA 704 (fire diamond) | 2-3-1-W |
| Flash point | 72 °C |
| Autoignition temperature | 435 °C |
| Explosive limits | Lower: 1.5% ; Upper: 10.6% |
| Lethal dose or concentration | LD50 (oral, rat): 131 mg/kg |
| LD50 (median dose) | LD50 (median dose): Oral rat 850 mg/kg |
| NIOSH | PA8575000 |
| PEL (Permissible) | PEL (Permissible Exposure Limit) for Ethyl Bromoacetate: 1 ppm (6 mg/m3) as recommended by OSHA. |
| REL (Recommended) | REL: 5 ppm |
| IDLH (Immediate danger) | 500 ppm |
| Related compounds | |
| Related compounds |
Ethyl iodoacetate
Methyl bromoacetate Bromoacetic acid Ethyl chloroacetate |
