Ethyl 2-Bromopropionate: Origins, Properties, Development, and Prospects
Tracing Ethyl 2-Bromopropionate's Early Days
Ethyl 2-Bromopropionate didn’t appear out of thin air. It rides on the shoulders of pioneers who sought practical and reproducible chemical transformations a century ago. Laboratories in Europe and North America scoured halogenated alkanoates for their synthetic range, laying groundwork in both academic and industrial settings. Early patents and chemical bulletins from the mid-1900s show interest in brominated esters for pharmaceutical intermediates and agricultural chemistry. Today’s protocols build on decades of methods for safe halogenation and refined esterification—without those earlier steps, chemists would still be stuck wrestling unreliable yield and poor purity in daily work.
Product Overview: More than a Simple Reagent
Ask around in any good organic lab, and someone will point to Ethyl 2-Bromopropionate as a reliable building block. This ester shows up as a colorless liquid with a distinct, slightly sharp odor. People prize it for the useful combination of reactivity and stability. It can sit on the shelf without fuss, yet still reacts briskly where needed. Its structure, with a bromine atom on the second carbon and an ethyl ester group, lends itself to substitution and elimination chemistry—key moves any synthetic chemist wants on call.
Physical and Chemical Properties: What You’re Handling
The compound boils at around 146-148°C under normal atmospheric pressure, which provides a safe working window for many reaction setups. With a density clocking in at about 1.38 g/cm³, it rests heavier in the flask compared to non-halogenated cousins. Ethyl 2-Bromopropionate dissolves well in common organic solvents like ether or chloroform, but water won’t easily mix with it. This hydrophobic nature makes it great for two-phase systems in extraction or workup. The bromine group gives it that signature reactivity, making nucleophilic substitution a breeze when forming new carbon-carbon or carbon-heteroatom bonds.
Technical Specs and the Labels That Matter
Read any commercial label—Ethyl 2-Bromopropionate’s purity often clocks in above 97%. NMR, GC, and titration methods certify what’s in the bottle. Packaging leans toward amber glass, tamper-evident seals, and chemical-resistant stoppers, protecting contents from light and accidental moisture seepage. Storage advice usually lines up with best practices for volatile brominated organics: keep cool, shield from direct sunlight, and avoid open flames or ignition sources in the vicinity.
Making It: Preparation Method in Practice
Labs prepare Ethyl 2-Bromopropionate using a reliable two-step process. They start with propionic acid or its ethyl ester, then treat with phosphorus tribromide or another brominating agent. The reaction often happens under cooling to control exothermicity, and careful distillation follows to purify the final product from any leftover acid or unreacted starting material. Waste streams receive neutralization with basic aqueous solutions—one of the less glamorous but important safety measures. Improper handling of reagents like PBr₃ has hurt more than a few enthusiastic chemists, so training and focus pay off big in this process.
Chemical Reactions and Structural Tweaks
This ester’s main claim to fame rests in its use as an alkylating agent. Chemists exploit the compound’s bromine to introduce the 2-propionate group onto nucleophiles—amines, thiols, enolates. The compound works in both batch and continuous flow systems, and its reactions extend to advanced pharmaceutical syntheses, chiral auxiliaries, and agrochemical side chains. Modifications include swapping out the ethyl group for others using transesterification, giving end users custom-tailored esters for further downstream chemistry.
Names Beyond the Basics: Synonyms and Product Tags
Depending on country, supplier, or the industry, Ethyl 2-Bromopropionate also arrives labeled as 2-Bromopropionic acid ethyl ester, Ethyl alpha-bromopropionate, or just "alpha-bromopropionic acid, ethyl ester." CAS number 535-11-5 usually follows closely behind. The variety in naming stems partly from the compound’s roots in both nomenclature systems and proprietary cataloging. Being aware of these alternate names helps avoid confusion, especially with customs forms or global purchasing.
Safe Handling and Operational Realities
Every technician who’s handled this liquid learns it stings the nose and should not touch skin. Ethyl 2-Bromopropionate can cause ophthalmic and dermal irritation. In poorly ventilated rooms, inhalation risk steps up. Working with appropriate gloves—nitrile, for best protection—and a lab coat matters. Face shields or goggles keep accidental splashes at bay. Chemical fume hoods provide a steady stream of airflow, pulling vapors away from breathing space. Labels demand proper disposal methods; waste mustn’t go down the drain. Even with solid protocols, spills do happen, so spill kits and absorbent materials stay nearby in professional facilities.
Where the Work Happens: Application Area
Pharmaceutical companies lean on Ethyl 2-Bromopropionate to build amino acid derivatives and synthetic intermediates. Industrial chemists include it in protocols for herbicide or fungicide precursors. Academic groups highlight it in methodology development, using it to demonstrate transition metal catalysis or asymmetric induction. Researchers value its role in introducing handles for further functionalization. The ester’s predictability and shelf stability mean it stays in regular rotation for both routine teaching labs and grant-funded research projects.
Innovation and R&D in Current Laboratories
Research teams continue advancing greener, less wasteful synthesis by tuning reaction temperatures, catalysts, or choice of solvent. Exploration into continuous flow setups promises better control, faster throughput, and improved safety, particularly by minimizing human exposure to hazardous reagents. Analytical scientists focus on tighter impurity profiling, aiming for higher purity without sacrificing yield. Some start-ups and multinational companies pour energy into new applications, guided by machine learning screens that predict novel couplings or biological activity for undiscovered analogs.
Looking Into Toxicity: What the Evidence Says
Toxicology studies flag risks of skin and respiratory irritation and highlight concerns for aquatic organisms. Exposure limits help shape workplace controls, and environmental monitoring ensures concentrations outside the plant perimeter don’t climb too high. New cell assays and animal models provide a finer-grain picture of metabolite fate and possible chronic effects, pushing industry toward formulations and usage scenarios that meet stricter environmental guidelines. Safety reviews update recommendations as fresh data comes in, so regulatory compliance requires a steady hand on the literature.
Where Progress Points: Future Prospects
Looking to the years ahead, demand for Ethyl 2-Bromopropionate shows no sign of slowing. The compound finds use in ever more selective chemical transformations, supported by advances in catalyst discovery and process safety. Environmental health and safety goals will continue influencing production scale and distribution. A shift toward biodegradable, less harmful alternatives could become a major driver for those able to match its unique chemistry with greener options. At the same time, the push for digitalization and automation in chemical production could redefine efficiency and control, letting chemists spend less time troubleshooting, more time innovating. Growth in bioactive molecule development, especially for unmet medical needs or sustainable farming, keeps this old-school brominated ester squarely on the radar for both industry giants and nimble research groups charting new paths forward.
Driving Forces Behind Chemical Synthesis
Ethyl 2-bromopropionate might sound obscure, but it draws real attention in chemical labs and factories. Chemists work with this compound for one main reason: its usefulness as a building block. The three-carbon chain, with a bromine atom clinging at just the right spot, makes this molecule a trusted starting point for building more complex chemicals. That piece—where the bromine hangs—turns out to be a pretty handy place for swaps and tweaks.
The Engine of Pharmaceutical Discovery
Talk to anyone in drug research, and they will share stories about hours spent hunting for new ways to make molecules that fight disease. Ethyl 2-bromopropionate fits into these stories as a foundation. Its reactive site lets scientists trade out the bromine for other groups, paving the path to entirely new compounds that can become medicines. Much of today's pharmaceutical pipeline depends on agile, flexible molecules.
The process often focuses on what's called “alkylation”—a way to connect small molecules into large, purposeful structures. In my time working alongside medicinal chemists, I saw how this molecule became the backbone for a range of candidate drugs. For example, its structure helps build amino acids, esters, and all sorts of specialized reagents. Some research even moves toward creating antiviral and anticancer compounds using it as a springboard.
Importance in Crop Protection
Take a walk through any modern farm, and behind the scenes you’ll discover a lot of chemistry. Ethyl 2-bromopropionate finds its way into the agrochemical world, where it shapes the formulas of herbicides and pesticides. Many crop-protecting substances start as simple molecules like this one. Getting the right functional groups in place allows companies to create powerful, selective weed- and pest-controlling ingredients. By leaning on these building blocks, food growers can support healthy yields and protect their investments from hungry bugs and stubborn weeds.
Wider Impact in Material Science
Not all impact lands in medicine or agriculture. Polymer scientists have also tapped into ethyl 2-bromopropionate. The molecule's reactivity helps create polymer chains with special features. Materials like coatings, adhesives, and specialty plastics benefit from such chemical roots. The role may not catch headlines, but these innovations show up in everything from electronics to sporting goods—places you wouldn’t expect.
Navigating Risks and Safety
Working with reactive chemicals carries risks. Anyone using ethyl 2-bromopropionate faces hazards due to its bromine content and strong odor. Skin contact, vapor exposure, and accidental spills can cause serious health problems. In every lab I’ve been, professionals learn to use gloves, fume hoods, and good judgment. This connects to broader principles of responsible science—prioritizing safety means more discoveries with fewer setbacks.
Building Toward Greener Chemistry
Every industry relying on reactive agents faces tough choices about waste and pollution. Brominated compounds, especially, can leave a tricky environmental footprint. More companies are thinking about alternative starting materials or better containment methods to limit unwanted byproducts. A smart move forward involves investing in research that finds greener pathways—methods that cut out toxic side products and protect both people and ecosystems.
Final Thoughts
Ethyl 2-bromopropionate stands as a behind-the-scenes driver in science and industry. From new medicines to advances in agriculture and materials, this simple molecule opens the door to real progress. By respecting the risks and seeking out safer, cleaner approaches, researchers create lasting value far beyond the lab bench.
Molecular Formula and Weight Matter for a Reason
Ethyl 2-bromopropionate often shows up in chemistry labs. Its molecular formula is C5H9BrO2, which means five carbon atoms, nine hydrogen atoms, a bromine atom, and two oxygen atoms make up the compound. Every experienced chemist recognizes how each element plays a role in both handling and application. The molecular weight checks in at 181.03 g/mol. Knowing these values can save hours during experiments, especially when precise measurements count.
What This Means for Students and Professionals
Young researchers might just see numbers in a textbook. After a few late nights puzzling over lab results, those numbers turn into vital tools. Ethyl 2-bromopropionate’s molecular makeup determines how it reacts and what safety measures are necessary. It fits squarely in the list of alkyl halides that introduce the bromo group into new molecules. This reactive nature makes it valuable in synthesis, but also a potential hazard with the wrong storage or disposal practice.
During my own undergraduate studies, I handled similar compounds and learned quickly that accurate molecular weights keep stoichiometry honest. One misplaced decimal could botch an entire synthesis. Many ambitious students ignore this, thinking calculators will catch their mistakes. Chemical safety and process efficiency rely on understanding a compound’s true identity. Imagine starting a project, buying bulk chemicals, just to realize later a simple mix-up in formula cost significant money and time.
Facts from Real Chemistry
Ethyl 2-bromopropionate’s bromine atom stands out. Bromine increases the molecular weight significantly. Chemists choose this compound for that specific property, especially in reactions that need heavier atoms or halogen introduction. Saponification of esters like this one produces bromo acids and alcohols, essential in creating medicines, flavors, and more. The compound’s volatile nature also calls for solid fume hoods—not something to skip, especially in academic labs.
Organic synthesis teams also use the ester group. Combine that with bromine’s reactivity, and you get versatility in building blocks for important molecules. Pharmaceutical researchers often turn to ethyl 2-bromopropionate to make starting materials for enzyme studies or cancer drug candidates. Understanding that molecular weight—181.03 grams per mole—means cost-effective scaling, especially if producing large batches. Waste management also depends on molecular identification. Labs with a reputation for safety double-check formulas before disposing, to avoid environmental fines or worse.
Improving Lab Practice and Efficiency
Simple strategies go a long way. Double-checking formulas against trusted chemical databases like PubChem helps avoid confusion. Laboratories posting clear molecular weights and formulas at every workstation makes things easier for everyone, from new technicians to experienced researchers. Students should practice calculating molecular weights by hand at least a few times, not just hitting up digital apps. This habit sharpens focus and can catch supplier mislabels, preventing batch contamination in high-stakes setups.
Ethyl 2-bromopropionate’s structure and value lie in the details. Knowing the exact formula and weight helps get the chemistry right and the workflow smooth. That’s a lesson learned the hard way by anyone who’s seen a reaction veer off course for want of double-checking a label or calculation. This practical attention to core details creates better results, yields, and most importantly, safer labs.
Recognizing the Hazards
Storing chemicals like ethyl 2-bromopropionate always makes me rethink the idea of “just keeping it on the shelf.” Anyone who has ever worked in a lab knows: a misplaced bottle or a loose cap can turn an ordinary day into something memorable for all the wrong reasons. This compound carries risks you can’t ignore. Inhalation, skin contact, or a spilled container could cause serious reactions. The sweet, fruity odor shouldn’t fool anyone. Every year, incidents happen because someone underestimates the dangers of proper chemical storage.
Storage That Puts Safety First
Storing ethyl 2-bromopropionate calls for a well-ventilated, cool spot away from sunlight. Heat speeds up decomposition, and that can get ugly fast. Friends who manage chemical storerooms often talk about the difference a simple dedicated ventilated cabinet makes. Direct sunlight or heat sources like radiators only tempt fate. Humidity creeps in through poor seals, and moisture can make some chemicals hydrolyze, producing unwanted byproducts or hazardous fumes. Keeping the bottle tightly sealed and double-checking the cap every time goes a long way.
Anyone stacking bottles together in open spaces risks more than just spills. Incompatible chemicals set off dangerous chain reactions—acid fumes, fire, or worse. I learned early to keep halogenated organics, like ethyl 2-bromopropionate, far from metals, bases, and oxidizers. Color-coded storage and clear labeling save you from scanning through worn-out stickers or relying on memory during late-night lab work.
Personal Protective Equipment: Not Optional
Latex gloves, goggles, and a sturdy lab coat stand between you and chemical burns or eye irritation. Rushing through work in regular clothes or skipping gloves opens the door to avoidable injuries. I’ve seen coworkers lose weeks of work to skin exposure from mishandling solvents because they figured “it’s just a drop.” Splash goggles, not just safety glasses, should be the norm for all transfers or pipetting. Thin nitrile gloves give just enough dexterity and protection, and changing them out if a splash happens prevents a minor problem from turning into a medical visit.
Practical Processes for Safe Handling
Transferring ethyl 2-bromopropionate should happen inside a fume hood every time. If a hood is taken up, waiting your turn beats the risk of exposure. Lifting or tilting containers over open benches spreads fumes instantly. For spills, spill kits aren’t just a suggestion locked away in the corner—you want them nearby, with neutralizers ready. Everyone should know where the eyewash or safety shower sits, and regular drills make sure no one panics during a real event.
Training new staff on safe chemical practices shouldn’t be a once-a-year slideshow. Rotating who gives safety talks or demonstrations gets more people thinking and watching for mistakes. Refresher sessions after a near-miss reinforce why these rules matter. Maintaining chemical safety in labs or storerooms boils down to respecting the risks every day, not just on safety inspection days.
Real-World Lessons in the Lab
Chemical safety doesn’t always grab headlines, but the wrong move with the wrong compound can change lives. In my early graduate days, I worked with Ethyl 2-Bromopropionate. Clear liquid, strong smell, label covered with warning symbols—no rookie ever forgot to wear gloves with this one. Just a splash on the skin could bring sharp irritation. Once, a classmate’s glove ripped, and even with a quick wash, a red welt stuck around for days. It’s a common wakeup call for chemists. Direct skin and eye contact from this chemical can produce much worse injuries. I now treat all halogenated organic compounds with double layers and fresh goggles, habits that never fade.
Vapor Dangers and Breathing Risks
Every time a bottle of Ethyl 2-Bromopropionate opens, a sharp scent escapes. Standing too close, even briefly, brings watery eyes and a cough. The material safety data sheet lists it as harmful if inhaled, and colleagues have reported headaches and sore throats after cleaning up an accidental spill. Fume hoods always run full steam in our lab—no exceptions. Extended exposure to its vapors can inflame airways and damage lung tissue. Those warnings aren’t just for show. In busy, poorly ventilated labs or factories, failure to control fumes can stack up risk and slow productivity as well.
Flammability and Fire Hazards
Ethyl 2-Bromopropionate may not light up as quickly as lighter hydrocarbons, but don’t mistake that for harmlessness. Flammable vapors concentrate around open bottles. Ignition sources linger everywhere: Bunsen burners, hot plates, even static from lab coats. At one plant tour, a minor fire broke out near a storage drum because a technician set down a heat gun nearby. Damage was contained, but the fire marshal’s report hammered home the point—any organic compound with a bromine atom demands respect. Good safety teams store this chemical in tightly sealed containers, away from open flames and anything that sparks.
Long-Term Health Concerns
Continuous, low-level exposure doesn’t always cause clear-cut symptoms right away. The long-term impact of handling organic bromides raises questions about chronic problems like asthma or liver stress. Some studies point to possible changes in blood chemistry in lab animals, though large-scale human data still falls short. I never discount gut feeling—cautious folks in the industry tend to rotate staff to limit long exposure, step up health screenings, and keep impeccable documentation.
Solutions for Staying Safe
Proper handling routines matter far more than slick protocols. Gloves, face shields, lab coats, strong ventilation, and rapid cleanup supplies stand ready at every bench I use. Labels wear down quickly when wiped, so fresh hazard icons help everyone spot the dangers in a rush. First-aid kits include supplies to counter chemical burns, and everyone knows exactly how to wash out eyes fast. Teams must communicate. Shared knowledge saves skin—literally. Community counts: No one shrugs off a small spill or skips the fume hood, because one careless act puts everyone at risk. Industry and academia keep learning—both from old mistakes and new incidents, adjusting policies to make handling safer each year.
Why Purity Makes All the Difference
Anyone who’s spent time measuring, weighing, or mixing chemicals can point to purity as a crucial detail, not just a box to tick. With Ethyl 2-Bromopropionate, most labs and manufacturers will look for options in the range of 97% up to 99%. Contaminants matter—even a percent or two of impurity can throw off results or compromise product stability. Pharmaceutical synthesis and specialty chemicals work demand consistency. If someone tried running a reaction with low-grade material, the yield could nosedive, or regulatory paperwork could hit a snag.
China and India source significant volumes, usually offering between 98% and 99%, while some Western suppliers stay in the high 99% range if buyers are chasing even tighter specs. GC analysis (Gas Chromatography) backs these purity claims, a must-have for quality control teams. And always, there’s a list of expected impurities—some ethanol, water, or trace bromides—which buyers check to ensure nothing comes back and bites the process down the line.
The Industry’s Go-To Specifications
Specification sheets usually read like a checklist. The CAS number for Ethyl 2-Bromopropionate is 535-11-5, and the formula C5H9BrO2. Every reputable source will include this, but the real meat lies in limits and appearances. Buyers expect a clear, colorless to pale yellow liquid, sometimes with a barely-there fruit scent. Acidity falls below 0.005%, checked by titration. Water content almost always sits under 0.1%, verified with Karl Fischer titration, since moisture impacts both shelf life and reactivity.
Assay by Gas Chromatography tells if a batch lives up to its promise—suppliers boasting an assay of 98.0% or higher gain more trust. Density hovers around 1.36–1.40 g/mL at 20°C. Boiling points show up too, typically between 155–160°C, which signals if a batch might have other volatiles mixed in. Refractive index (often not exceeding 1.4340 at 20°C) gives buyers an extra angle to double-check consistency batch to batch.
Real Quality Means Real Accountability
Every time a chemist uncorks a new bottle, that accountability echoes. Regulatory compliance means more than following a spec sheet; it calls for documentation and transparent batch tracing. Some environments—drug R&D, pesticides, electronic materials—require certificates of analysis with every delivery. Buyers check for heavy metals, residual solvents, and halide content especially if any toxicological concern lingers in the end-use.
Storing Ethyl 2-Bromopropionate highlights another critical point: humidity and air exposure erode both shelf life and integrity. Tight sealing, cool rooms, and amber glass minimize breakdown and keep acids from forming. Over my years in labs, I’ve seen more than one otherwise decent bottle wasted simply because storage details got ignored. And since this compound can serve as an intermediate for active pharmaceuticals, every spec and precaution doubles in importance.
Paths Toward Better Practice
Manufacturers ramp up their analytical work to keep up with changing expectations. Adding HPLC and advanced spectroscopy catches impurities before they cut into downstream results. Suppliers can boost confidence by sharing batch testing reports, plus providing stability data on degradation.
Those in charge of procurement should press for up-to-date safety sheets and push for dialogue around actual use cases. Not every application demands 99.5%; for some, 97% paired with detailed impurity profiling saves both cost and headaches downstream. Decision-makers win big by insisting on clear paperwork and direct, no-BS supplier relationships.
In the end, specifications for Ethyl 2-Bromopropionate aren’t just fine print—they’re a handshake of trust between manufacturer, lab bench, and the compliant products that follow. As standards inch upward, both transparency and practical handling make a world of difference.
| Names | |
| Preferred IUPAC name | Ethyl 2-bromopropanoate |
| Other names |
Ethyl α-bromopropionate
2-Bromopropionic acid ethyl ester Ethyl 2-bromopropanoate |
| Pronunciation | /ˈiːθɪl tuː ˌbrəʊməʊprəˈpɒneɪt/ |
| Identifiers | |
| CAS Number | 535-11-5 |
| Beilstein Reference | 3581331 |
| ChEBI | CHEBI:113278 |
| ChEMBL | CHEMBL2151800 |
| ChemSpider | 54672 |
| DrugBank | DB13983 |
| ECHA InfoCard | 03b9669e-fada-44c4-94ae-381fc752f586 |
| EC Number | 205-804-1 |
| Gmelin Reference | 7378 |
| KEGG | C06423 |
| MeSH | D017225 |
| PubChem CID | 12309 |
| RTECS number | UF9100000 |
| UNII | QTI9G2FA3B |
| UN number | UN2342 |
| CompTox Dashboard (EPA) | urn:cpdat:2800 |
| Properties | |
| Chemical formula | C5H9BrO2 |
| Molar mass | 181.04 g/mol |
| Appearance | Colorless to yellow liquid |
| Odor | sweet |
| Density | 1.464 g/mL at 25 °C(lit.) |
| Solubility in water | slightly soluble |
| log P | 0.97 |
| Vapor pressure | 1.2 mmHg (20°C) |
| Acidity (pKa) | 21.0 |
| Magnetic susceptibility (χ) | -7.89 × 10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.4360 |
| Viscosity | 1.613 cP (20°C) |
| Dipole moment | 2.05 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 199.7 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -516.6 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -1992.7 kJ/mol |
| Pharmacology | |
| ATC code | |
| Hazards | |
| GHS labelling | GHS02, GHS07 |
| Pictograms | GHS07 |
| Signal word | Warning |
| Hazard statements | H315: Causes skin irritation. H319: Causes serious eye irritation. H335: May cause respiratory irritation. |
| Precautionary statements | P210, P261, P264, P271, P301+P312, P305+P351+P338, P337+P313 |
| NFPA 704 (fire diamond) | 2-2-0 |
| Flash point | 70 °C |
| Autoignition temperature | 437 °C |
| Explosive limits | Upper: 12%; Lower: 2.2% |
| Lethal dose or concentration | LD50 oral, rat: 2,850 mg/kg |
| LD50 (median dose) | LD50 (oral, rat): 2,255 mg/kg |
| NIOSH | VJ8925000 |
| PEL (Permissible) | PEL: Not established |
| REL (Recommended) | REL (Recommended Exposure Limit) for Ethyl 2-Bromopropionate is: "No REL |
| Related compounds | |
| Related compounds |
Methyl 2-bromopropionate
Isopropyl 2-bromopropionate Ethyl 2-chloropropionate Ethyl 3-bromopropionate Ethyl 2-bromoacetate n-Propyl 2-bromopropionate |
