Tert-Butyl Bromoacetate: Progress, Properties, Safety, and Prospects
Historical Development
Once, organic synthesis stayed limited by unreliable reagents and inconsistent purity. Rewinding to the roots of tert-butyl bromoacetate, chemists in the early 20th century dealt with simple bromoacetic acid chemistry, though with frequent problems from corrosivity and instability. Tert-butyl esters changed that game. By the 1950s and 1960s, a new focus on protecting groups in peptide synthesis and pharmaceutical laboratories led scientists to tert-butyl bromoacetate. Its stable tert-butyl group buffered sensitive molecules through rough synthesis steps, helping researchers make purer compounds and expand their toolkits for everything from new antibiotics to early HIV therapeutics. As time marched on, researchers traded notes on improved routes of synthesis, tweaking reaction times and solvents for better yields.
Product Overview
Tert-butyl bromoacetate stands out as a reagent, acting as a building block in the preparation of esters and as a reliable alkylating agent. Chemists appreciate its compact design: a bromine atom, highly reactive, paired with the familiar tert-butyl group, which retreats with a bit of acid or base when chemists call for it. Many research suppliers carry it in liquid form, sometimes off-white, sometimes nearly clear, depending on how well the storage and handling procedures have kept water and air at bay. Those who have worked with this compound usually know its distinctive, sharp scent – a reminder of potent reactivity. Chemical suppliers label containers tightly, noting hazards and the need for lab gloves and goggles.
Physical & Chemical Properties
This chemical sits in a liquid state at room temperature, with a boiling point near 156°C and a molecular weight around 195.07 g/mol. It dissolves readily in common solvents such as dichloromethane and ether, opening up wide avenues for transformation. Tert-butyl bromoacetate doesn't resist hydrolysis in water, especially if traces of acid lurk around. The ester group makes it easier to handle than free bromoacetic acid, reducing volatility and making it less strenuous on standard glassware. In air, it tends to stay stable unless hit with strong bases, acids, or nucleophiles. That simple change – swapping a hydrogen for a tert-butyl group – lengthens its shelf life and makes storage less maddening.
Technical Specifications & Labeling
Every container has a list of essentials: chemical purity (usually north of 97%), CAS number 5292-43-3, molecular formula C6H11BrO2. Reliable suppliers provide certificates of analysis, NMR and GC-MS purity results, and detailed safety warnings. The bottle usually comes lined with a PTFE cap to avoid leaks or corrosion, wrapped in absorbent material to trap any accidental spills. You’ll catch pictograms showing acute toxicity, an exclamation mark for irritation, and stern warnings about skin contact. Labels avoid ambiguity, spelling out exact concentrations for solution forms and marking batch lot numbers.
Preparation Method
Labs typically prepare tert-butyl bromoacetate by esterifying bromoacetic acid with isobutylene in the presence of a strong acid like sulfuric acid, or by treating bromoacetyl chloride with tert-butyl alcohol and a mild base. Some large-scale processes swap these reagents for less hazardous chemicals, but the principle stays the same: build the tert-butyl ester, then append the bromine. In my own experience, careful control of water and temperature during the reaction keeps side products minimal, though patience becomes vital when pushing for those final few grams of yield.
Chemical Reactions & Modifications
Tert-butyl bromoacetate earns its keep as an alkylating agent, introducing the bromoacetate group to nucleophiles such as amines or thiols, and paving the way for new peptide bonds or couplings. After the desired reaction, chemists can strip off the tert-butyl group using trifluoroacetic acid or even acidic resins, freeing the bromoacetic acid for subsequent transformations. In multistep syntheses, it acts as a “masked” version of bromoacetic acid, passing through harsh reaction steps that might otherwise tear the molecule apart. Many medicinal chemists rely on it to build molecules in a stepwise, modular way, giving them test compounds with high purity for biological assays.
Synonyms & Product Names
Those who look through literature may find tert-butyl bromoacetate under a patchwork of alternative names: 2-bromoacetic acid tert-butyl ester, Bromoacetic acid tert-butyl ester, or simply “TBBA.” Each catalog or supplier might use house brand labels, but the structure always comes back to the same skeleton. While this can get confusing for young researchers, seasoned synthetic chemists quickly catch on. A quick scan of the CAS number often clears up mixups.
Safety & Operational Standards
Working with this compound demands common-sense lab protections. Nitrile gloves, goggles, and a strong extractor fan save researchers from skin or eye contact. Even brief exposure can trigger redness, irritation, or chemical burns. Inhalation brings risk of respiratory distress and nausea. Storage guidelines keep the chemical in cool, dry conditions with tight seals – any water will eat away at it, sometimes generating hazardous fumes. Labs teach their teams safe disposal in halogenated waste streams, not regular drains, to avoid environmental contamination. Many manufacturers push for improved packaging with tamper-evident seals and informative labeling, reducing chances of an accident. Strict training remains the backbone of handling – no shortcut ever ends well in the long run, as accidents with alkylating agents can bring hidden, long-term health problems.
Application Area
The versatility of tert-butyl bromoacetate drives its use in drug discovery workflows and polymer chemistry. Chemists reach for it when crafting peptide and oligonucleotide intermediates, especially where flexible blocking and deprotection tactics are crucial. In the hands of radiochemists, tagged versions become radiolabeling reagents for specialized imaging agents. Agricultural researchers turn to it while exploring modifications of bioactive molecules to boost selectivity or reduce side effects. Its role rarely ends in the marketed product; the compound works behind the scenes, enabling late-stage modifications or helping introduce robust, functional linkers.
Research & Development
The story of tert-butyl bromoacetate remains in motion, shifting as organic chemistry tools advance. Many academic and industry labs now pursue greener, higher-yielding synthesis strategies, swapping out harsh solvents or acids for milder and more sustainable reagents. Some projects focus on broadening the scope of coupling reactions – not just with nitrogen nucleophiles but also with complex heterocycles or peptide chains. In my own encounters, I’ve seen young researchers develop micro-scale “flow” systems that automate addition and workup, saving hours and reducing waste. As demand grows for tailor-made building blocks, small manufacturers now offer custom derivatives, tested and packaged for specific R&D pipelines.
Toxicity Research
Whenever a compound sees wide use in chemical synthesis laboratories, toxicity data builds up over years. Tert-butyl bromoacetate poses sharp risks by skin, eye, or inhalation exposure. Animal studies highlight the harm relies on bromine’s high reactivity: damage comes not just from its direct effect, but also from toxic metabolites released after hydrolysis and breakdown. Chronic low-level exposure can lead to organ irritation and possible long-term damage in poorly ventilated settings. Despite this, modern labs and manufacturing plants maintain low incident rates thanks to mandatory risk assessments, strong engineering controls, and worker medical monitoring. Efforts keep evolving; testing now often involves more accurate in vitro models and expanded environmental fate studies, helping regulators assess broader impacts beyond immediate lab exposures.
Future Prospects
The next decade will likely see tert-butyl bromoacetate pushed into new frontiers, partly because researchers want safer, cleaner, and more scalable synthesis. Startups and academic groups are chasing benign catalysts, recyclable solvents, and automated purification platforms that treat hazardous byproducts before they leave the fume hood. Interest grows in using bio-based feedstocks for its synthesis, tying into the broader push for sustainable chemistry. The shift toward high-throughput miniaturized screening in drug discovery could drive higher demand, as researchers look for custom-labeled or tagged versions for fast hit validation. Regulatory trends point toward stricter labeling and exposure guidelines, improving transparency about what goes into every flask. In the long run, the reliability and adaptability of tert-butyl bromoacetate give it an enduring spot on the chemical workbench, as long as researchers and manufacturers keep their eyes on safety, sustainability, and robust supply chains.
Why Formula Matters Beyond Chemistry Class
Chemistry feels distant to plenty of folks—the kind of topic that faded from memory after high school labs. Still, a compound like Tert-Butyl Bromoacetate has a bigger role than most people realize. Its chemical formula, C6H11BrO2, might look cryptic, but it helps chemists control the way medicines, dyes, and other chemicals come to life.
Understanding formulas becomes vital the deeper you get into healthcare, agriculture, or materials science. C6H11BrO2 describes not just the kinds of atoms in Tert-Butyl Bromoacetate but also the rules those atoms follow. Mess up the formula—a missed hydrogen, a swapped bromine for chlorine—and suddenly a harmless reagent turns unsafe or ineffective. The margin for error stays tight when you scale up production. I’ve watched junior chemists stress over simple transcription errors, and that’s enough to send a whole chemical batch down the drain.
This Compound’s Real-World Applications
Folks outside labs might shrug at chemical details, but they’re everywhere in the things people use daily. Tert-Butyl Bromoacetate, with its six carbons, eleven hydrogens, one bromine, and two oxygens, fits the bill as a starting material for pharmaceuticals. Chemists often use it because it reacts in predictable ways, transforming into building blocks for antiviral drugs or anti-inflammatory agents. It’s also handy in peptide synthesis, where reactive intermediates need to behave themselves without surprise side-effects.
Getting the formula right leads to safer manufacturing. Consider the challenge: batch reactions scale up to hundreds of liters, and any slip-up—wrong ingredient, off-ratio—means wasted resources and potential hazards. Firms face sharp fines and long-term costs if they mismanage hazardous compounds. Bromo-group containing substances demand respect because bromine’s reactivity can trigger environmental and personal safety emergencies. I’ve walked through plants where Floor Supervisors double-check raw materials every morning, knowing a single mislabelled bottle spells trouble.
Accuracy Means Safety and Innovation
C6H11BrO2 as Tert-Butyl Bromoacetate tells regulatory bodies what to expect. Environmental agencies need this information for audits and spill responses. Emergency rooms depend on it too; if someone has an exposure incident, clinicians want exact formulas for quick action. Over my own years working with chemicals, nothing beats the relief of handing paramedics a straight answer about what they’re dealing with, instead of a blind guess.
Innovation relies on these formulas. Startups hunting for new antiviral molecules bank on known compounds like Tert-Butyl Bromoacetate as stepping stones. Synthetic pathways grow more complex each year, but they all stand on the shoulders of well-understood reagents. A single typo in notes from the lab bench can slow projects by weeks.
Improving Chemistry Culture and Practice
Chemistry educators carry a heavy responsibility. Memorization alone doesn’t foster understanding or safe habits. Younger chemists learn to double-check everything, especially formulas like C6H11BrO2, because the cost of being sloppy stays high. Companies encourage an environment where slowing down to verify every calculation earns praise, not side-eye. Technology helps out too, with modern lab software flagging mistakes before any mixing begins.
Perhaps most importantly, real trust emerges through shared vigilance: everyone from interns to senior scientists reviews labels, recipes, and logbooks. Safe practices and clear formulas keep industry efforts moving forward, protecting both people and progress. That’s the mark of responsible science—and a culture worth building, one correct formula at a time.
Making Molecules for Medicine
I’ve always found drug discovery fascinating—so much skill goes into piecing together the right molecules. Tert-butyl bromoacetate plays a subtle yet vital role in this process. Chemists often pick it for making building blocks used in pharmaceutical research. The tert-butyl group provides stability during complex reactions, protecting other sensitive parts of the molecule.
The real game changer comes in amino acid chemistry and peptide synthesis. Building peptides involves adding and trimming groups from molecules like you’re assembling a puzzle. Tert-butyl bromoacetate helps introduce carboxylic acid fragments in a controlled way, smoothing the process of chaining together critical biological molecules. This cuts down on failed reactions and wasted resources, which always matters in a high-stakes lab environment.
Preparing Fine Chemicals
Research labs and chemical manufacturers keep tert-butyl bromoacetate on hand as a reliable alkylating agent. Picture a chemist needing to add a specific fragment onto a growing ring-shaped molecule. This compound provides the bromo (or bromide) unit, which acts as a handy “handle” for connecting other pieces. The tert-butyl ester group, which is bulky and protective, keeps that section of the molecule from reacting at the wrong moment. After the heavy lifting is done, a few steps can strip away the protective group, revealing a useful acid ready for the next stage.
This stepwise approach brings more precision and fewer unwanted byproducts. Time lost troubleshooting impure batches in the lab often means slower progress, higher costs, and missed deadlines. Tert-butyl bromoacetate supports a smoother process by cutting down on these headaches.
Expanding the Toolkit for New Materials
Many fields push for smarter, more efficient materials—think of plastics, coatings, or polymers designed for specific jobs. Chemists use tert-butyl bromoacetate as one of their tools for tweaking molecular structures. It helps introduce key fragments onto a backbone, creating sites for future modification.
For example, in crafting specialty polymers that show unique properties (like temperature sensitivity or selective permeability), scientists often build up from core monomers. The compound at hand lends itself to controlled reactions, delivering structure where it’s needed without derailing the process with unwanted side reactions. Getting this right opens possibilities, whether it’s a self-healing coating or a sensor that reacts to its environment.
Steps Toward Safer Laboratories and Cleaner Chemistry
In my time spent with chemistry researchers, safety conversations come up regularly. Tert-butyl bromoacetate’s use calls for careful handling. It can be toxic and irritating, especially with skin or inhalation exposure. Labs working with it usually enforce gloves, goggles, and fume hoods as standard practice. Proper waste disposal keeps harmful residues out of the water supply and air. Good safety training and modern fume extraction systems reduce incidents, letting teams focus on the science.
Green chemistry advocates also push for better substitutes where they improve environmental impact. Some labs explore milder alkylating reagents or hope for even safer protocols using the same protective groups. Education on best practices continues to play a key role in making advanced chemistry both productive and responsible.
Moving Science Forward, One Compound at a Time
In the end, tert-butyl bromoacetate does more than sit on a reagent shelf. It connects the dots between research, product development, and safe workplace practice. Learning from each project, scientists refine their choices to create value for medicine, industry, and society.
Why Tert-Butyl Bromoacetate Needs Careful Storage
Tert-Butyl Bromoacetate often shows up in organic chemistry labs, popping up in synthesis work or drug discovery. People who use or store this chemical get serious about handling because it doesn’t forgive carelessness. Ask any chemist who’s cleaned up after a leaky bottle in a fume hood—responsibility starts with storage.
Understanding the Hazards
Tert-Butyl Bromoacetate has a fairly volatile personality. Flammability, corrosive action, and potential for toxic fumes aren’t just small print in the safety data sheet. The chemical can bite skin and eyes, and if left exposed, it starts breaking down, sometimes without much warning. Leaks or accidental contact can turn a quiet lab session into an emergency.
Temperature and Environment Matter
People who store this compound should keep it in a cool spot, usually below 8°C. Heat forces decomposition, so even a lazy fridge shelf is far safer than a room that gets sunlight or fluctuates through the seasons. If you’ve ever watched a bottle sweat in a warm lab, you know that just a few degrees can start affecting stability. On a hot summer day, one failed air conditioner can change everything in a matter of hours.
Containers Make a Difference
Tert-Butyl Bromoacetate plays well only with glass or well-chosen plastic containers that don’t react with bromine or esters. The cap must seal tightly—those disposable plastic wraps folks sometimes use with food storage just invite fumes and evaporation. A container that doesn’t fit tightly or gets reused inappropriately brings risk that’s easy to avoid with a little discipline and the right supplies.
Labeling and Segregation
Clear labels belong on each container, with the name, concentration, and the date it arrived on the shelf. Some people add hazard warnings or emergency instructions—such habits cost nothing but pay off in clarity and safety. Storing this chemical away from acids, bases, and water sources helps prevent unplanned reactions. I’ve seen rushed workers stumble into trouble by stashing incompatible chemicals together on crowded shelves, distracted after a long day or lulled by routine.
Handling Routine
Wear gloves, safety glasses, and a lab coat when reaching for tert-butyl bromoacetate. More than one person has reached for a quick transfer or measurement only to remember too late that chemical burns don’t mess around. Fume hoods aren’t just for dramatic experiments, either—they keep low-level exposure out of your lungs, day after day.
Spill Plans and Disposal
No matter how careful the team, spills happen. Absorbent materials go right next to storage areas, not buried in a distant supply closet. Training everyone in cleanup and proper disposal removes confusion and panic from tense moments. Designated waste containers for halogenated solvents mean the chemical chain stays unbroken.
Building Solid Habits
Labs that make these storage standards routine run smoother and safer. New chemists learn from the veterans who never cut corners. Establishing smart habits lowers risks, keeps projects on track, and helps everyone reach the end of the day without incident—common sense at every step.
Chemical Work Demands Respect
Tert-Butyl Bromoacetate often shows up in research labs and chemical synthesis work. Over my years around labs, certain chemicals, even if they don’t carry explosive warnings, still make me uneasy. This one fits that category. Tert-Butyl Bromoacetate carries a reputation for being more than just a mild irritant. Anyone who’s spilled a few drops on their gloves knows you don’t ignore it; the fumes hit the nose and throat, and the sharp, persistent odor lingers long after cleanup.
Health Risks and Real-world Exposure
Stories matter more than safety data sheets. Friends in organic chemistry have shared close calls: red eyes, persistent coughing, headaches after accidental whiffs in poorly ventilated spaces. The warning labels—irritant, toxic by inhalation and skin absorption—reflect what chemists have learned the hard way.
Once this chemical touches skin, it doesn’t just annoy; it burns. Direct contact sometimes leaves a scar. Overexposure to vapors can lead to serious respiratory distress. I remember one lab closing shop early after a poorly sealed bottle leaked, forcing everyone outside as headaches spread. The material can also cause liver and kidney damage with repeated or large-scale exposure. That’s not mere speculation—it lines up with animal studies and lab safety incidents documented in industry case reports.
Why the Threat Goes Beyond the Lab
Some solvents and reagents feel safe, especially with gloves and goggles. Tert-Butyl Bromoacetate lowers that comfort margin. It’s not only about burning eyes or stained gloves. This chemical finds its way into waste streams. Small spills on the floor can evaporate and affect many people in the building. Labs in older buildings may not have the best ventilation, multiplying the hazard. Poor handling creates risk for everyone in the area, not only the person working directly with the bottle.
Responsible Handling Changes the Risk
Fume hoods and full-face shields do more than check boxes. Always treat tert-Butyl Bromoacetate as a chemical demanding containment and planning. I’ve learned to keep neutralizing agents handy and never turn my back on an open container, even for a moment. Never trust a used glove—replace it. Store the chemical away from acids, bases, and open flames. Dispose of it quickly and responsibly. Every staff member in the space, even those outside chemistry, deserves training on what that faint fruity odor might mean.
Better Habits and Shared Responsibility
I have seen teams adopt new routines after a close call—eye wash stations tested weekly, fume hoods re-certified twice a year, and notes left on every hazardous bottle. It’s easy to think one person’s care matters less, but someone else might come into contact with forgotten droplets the next day. Regular air checks in older labs provide real information, not just peace of mind.
Conclusion: Respect Chemical Hazards
Every chemical professional benefits from honest stories and real-world cases. Tert-Butyl Bromoacetate can seem routine—until something goes wrong. Over the years, I’ve seen that respect for chemicals grows from learning, not ignoring the risks. By building routines, encouraging immediate cleanup, and talking frankly about hazards, everyone goes home safer.
Looking Closely at This Chemical
Tert-Butyl bromoacetate carries the formula C6H11BrO2 and tips the scale at 211.06 g/mol on the molecular weight front. Chemists will tell you, it’s not simply about memorizing that number. In the lab, that value unlocks more than conversions on paper—it helps shape choices that eventually influence outcomes down the line, whether it’s designing a synthetic route for a medication or scaling up to create a consumer product.
The Weight Sets the Stage for Synthesis
Organic synthesis has always felt like navigating with a map—you need coordinates and clear paths, or you get lost along the way. Molecular weight stands tall as one of those guiding posts. Take Tert-Butyl bromoacetate. Its molecular heft doesn't just fill a space in a textbook table. That figure controls how much to weigh out to get a precise mole. Miss that by a few grams and the difference multiplies in every reaction step down the line. This chemical gets picked often as an alkylating or esterifying agent. Small errors snowball. During grad school, I watched a newcomer underestimate the accuracy needed and the final product yield suffered—an expensive lesson.
Safety Connects Directly to Molecular Size
Molecular weight ties straight into basic safety. Inhaling or spilling a large amount of Tert-Butyl bromoacetate without understanding its density or volatility can go sideways. Heavier compounds behave a bit differently—sometimes lingering where you’d expect them to disperse, sometimes reacting more aggressively. Safety data sheets always mention molecular weight for a reason. Calculating exposure limits, fume hood settings, and even fire risk comes down to that figure. I’ve seen an incident where a miscalculation meant PPE wasn’t chosen properly, and it led to a bad day for a colleague with skin irritation. Handling chemicals without detailed knowledge, especially something reactive like a bromoacetate, isn’t a guessing game.
Drug Development and Manufacturing Relies on These Details
The pharmaceutical world runs on tight tolerances. Tert-Butyl bromoacetate sometimes plays a role in assembling building blocks for active pharmaceutical ingredients. Its molecular weight helps production chemists figure out how much solvent to add, how long a reaction should run, and the kinds of purification needed. Even pricing and shipment calculations use this number. I remember a manufacturing setup where an overlooked decimal on molecular weight forced a recalculation of every batch sheet, eating up hours and money. Nearly every cost-saving process hinges on nailing the math early.
Accuracy Is the Start of Trust
Trust in a research or industrial process starts with honest, careful measurements. That 211.06 g/mol forms the bridge between a scribble in a lab notebook and a real product people might use or ingest. Application guides and regulatory documents never skip over this figure, showing respect not just for scientific tradition, but for the real risks and responsibilities at stake. I always tell new technicians—the smallest details, like a molecule’s weight, anchor the whole process.
Building Better Habits with Solid Knowledge
In my experience, giving attention to things like molecular weight pays off in speed, confidence, and fewer surprises. For those using Tert-Butyl bromoacetate, reading the label is just the first step. Understanding that 211.06 isn’t just a background number, but the core of every decision, improves lab work, keeps people safer, and smooths out headaches from procurement to production. We can unlock real progress by focusing on fundamentals, and molecular weight is as fundamental as it gets.


| Names | |
| Preferred IUPAC name | tert-butyl 2-bromoacetate |
| Other names |
Bromoacetic acid tert-butyl ester
tert-Butyl 2-bromoacetate t-Butyl bromoacetate 2-Bromoacetic acid tert-butyl ester |
| Pronunciation | /ˌtɜːrtˈbjuːtɪl broʊˈmæsoʊteɪt/ |
| Identifiers | |
| CAS Number | • "5292-43-3 |
| 3D model (JSmol) | ``` C(C(=O)OC(C)(C)C)Br ``` |
| Beilstein Reference | 1721394 |
| ChEBI | CHEBI:52034 |
| ChEMBL | CHEMBL429027 |
| ChemSpider | 69834 |
| DrugBank | DB14115 |
| ECHA InfoCard | 06e07b0c-7b8b-49b0-bf26-c7d80c24c8b9 |
| EC Number | 602-215-0 |
| Gmelin Reference | 81898 |
| KEGG | C06928 |
| MeSH | D017653 |
| PubChem CID | 12540 |
| RTECS number | EO1575000 |
| UNII | 174UD7H929 |
| UN number | 3265 |
| Properties | |
| Chemical formula | C6H11BrO2 |
| Molar mass | 181.06 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Odor | pungent |
| Density | 1.286 g/mL at 25 °C (lit.) |
| Solubility in water | Insoluble |
| log P | 1.93 |
| Vapor pressure | 0.4 mmHg (20°C) |
| Acidity (pKa) | 23.5 |
| Basicity (pKb) | 1.99 |
| Magnetic susceptibility (χ) | -6.18 × 10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.437 |
| Viscosity | 2.09 cP (20°C) |
| Dipole moment | 2.51 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 383.6 J·mol⁻¹·K⁻¹ |
| Pharmacology | |
| ATC code | Not assigned |
| Hazards | |
| GHS labelling | GHS02, GHS07 |
| Pictograms | GHS02, GHS07 |
| Signal word | Warning |
| Hazard statements | H302, H315, H319, H335 |
| Precautionary statements | P210, P261, P280, P301+P312, P305+P351+P338, P337+P313 |
| NFPA 704 (fire diamond) | 1-2-0 |
| Flash point | 80 °C |
| Lethal dose or concentration | LD₅₀ (oral, rat): 2,400 mg/kg |
| LD50 (median dose) | LD50 (median dose) of Tert-Butyl Bromoacetate: "780 mg/kg (rat, oral) |
| PEL (Permissible) | Not established |
| REL (Recommended) | 50 ppm |
| IDLH (Immediate danger) | Not established |
| Related compounds | |
| Related compounds |
Bromoacetic acid
Ethyl bromoacetate Methyl bromoacetate tert-Butyl chloroacetate tert-Butyl acetate |