Methyl 2-Bromohexanoate: Insights Into Its Evolution, Properties, and Role in Modern Chemistry
Historical Development
Methyl 2-bromohexanoate caught the attention of synthetic chemists in the mid-20th century, right at the juncture where organic halides started playing a larger role in laboratory transformations and industrial synthesis. Back then, laboratories prioritized reliable building blocks that enabled creation of more complex compounds, and the brominated esters offered a way to introduce functional diversity into organic molecules. During my early years in chemical research, stories from the previous generation often painted a picture of chemists laboring over glassware and distillation columns, learning the hard way that bromination provided a handle for further transformation. Chemists built on these findings and began to appreciate how introducing a halogen to an ester backbone added flexibility in multi-step synthesis.
Product Overview
Methyl 2-bromohexanoate serves as a highly adaptable intermediate. It sits in a category of organic esters enhanced with a bromine atom at the 2-position. My colleagues and I have found this type of compound reliable for nucleophilic substitution and other functional group manipulations that underpin pharmaceutical development. Organic chemists appreciate these esters because they deliver predictable reactivity, and the methyl group at the ester end minimizes steric hindrance, making the compound amenable to alkylation and modification.
Physical & Chemical Properties
On the bench, methyl 2-bromohexanoate usually appears as a clear to slightly yellowish liquid with a moderately strong odor. Its boiling point commonly sits above 200°C, which helps during procedures that involve prolonged heating. The compound has limited water solubility but dissolves well in most organic solvents like ether or dichloromethane. Chemical reactivity springs mostly from the polar carbon-bromine bond at the second carbon, which stands ready for nucleophilic attack. A feature that stands out is the balance it offers: it isn’t so reactive as to threaten stability during routine handling, but it delivers solid yields in substitution and elimination reactions.
Technical Specifications & Labeling
Suppliers usually offer methyl 2-bromohexanoate with a purity of 97% or higher, which aligns with synthetic needs for research applications. Standard labels list details such as the molecular formula (C7H13BrO2), molar mass, CAS number, storage temperature recommendations (generally 2-8°C), and hazard warnings—an aspect I always look for before ordering chemicals for my team’s projects. Clear handling advice and mechanisms for traceability matter greatly, since they uphold safety in academic and industrial settings. Reliable suppliers also provide certificates of analysis, allowing chemists to corroborate the identity and purity using NMR or GC-MS.
Preparation Method
Synthesizing methyl 2-bromohexanoate typically begins with esterification of 2-bromohexanoic acid and methanol under acidic conditions, sometimes involving a catalytic amount of sulfuric acid. The acid is dissolved in methanol, and the mixture warms gently; water formed during the reaction can be drawn off using a Dean-Stark apparatus or removed under reduced pressure. This step reliably yields a product suitable for further purification, usually distillation under reduced pressure. I have often found that substituting alternative brominating agents leads to lower selectivity and more complex purification, so the direct esterification route remains a favorite for both lab-scale and modest commercial batch preparation.
Chemical Reactions & Modifications
The alpha-bromo group on methyl 2-bromohexanoate unlocks a range of transformations. Nucleophiles such as amines, thiols, or alkoxides readily displace the bromine, opening up straightforward paths to amino, thio, or ether derivatives. Alkylation reactions can yield quaternary centers, a structure prized in the synthesis of certain herbicides and pharmaceuticals. Reacting the ester with bases promotes elimination to install alkenes, offering a way to diversify molecular frameworks. I’ve used this one-pot method as a teaching tool for students to illustrate key reaction mechanisms like SN2 displacement and E2 elimination, revealing the full power of this deceptively simple molecule.
Synonyms & Product Names
In lab catalogs and research papers, methyl 2-bromohexanoate comes up under several synonyms. Among these: hexanoic acid, 2-bromo-, methyl ester; methyl alpha-bromohexanoate; and methyl 2-bromo-n-hexanoate. Recognizing these names on datasheets prevents costly ordering mistakes and confusion during experimental write-ups. Sometimes commercial vendors even use proprietary brand names for purity-graduated grades aimed at pharmaceutical or research customers.
Safety & Operational Standards
Labs operating with methyl 2-bromohexanoate rely on standard protocols for handling organobromines, since these can irritate the skin, eyes, and respiratory tract upon exposure. Training students and lab staff remains more important than ever—an ER visit for inhalation or skin contact leaves lasting memories. Appropriate fume hoods, nitrile gloves, and face protection make up the backbone of safety policies. Importantly, spill kits and neutralizing agents stay close at hand during syntheses, and clear labeling prevents accidents during storage. Waste management also comes under scrutiny, as brominated compounds must be kept separate from general organic waste streams.
Application Area
Pharmaceutical research taps into the utility of methyl 2-bromohexanoate in peptide synthesis, where its brominated alpha-carbon enables controlled coupling reactions. Agrochemical development teams pursue routes to novel herbicides or plant protectants by leveraging the easily modified structure of this ester. Academic groups exploring advanced organic synthesis value this molecule as a platform for teaching key reaction types, all the way through to complex molecular scaffolds. Drawing on my own work, I’ve seen this ester serve as a bridging compound when constructing beta-amino acids and tailor-made intermediates for biologically relevant molecules.
Research & Development
Continual research aims to expand the transformation repertoire of methyl 2-bromohexanoate. Chemists increasingly look to metal-catalyzed couplings and asymmetric synthesis using this ester as a starting material. Innovation includes exploring greener bromination methods and searching for catalysts that streamline transformations, cuts on hazardous waste, and improves selectivity. At a previous conference, I witnessed groups reporting on expanding nucleophile compatibility, hoping to access new families of functionalized hexanoate derivatives with application in material science and drug discovery. Engineers and process development chemists also seek to adapt batch syntheses to continuous-flow setups, hoping for safer and more scalable options.
Toxicity Research
Toxicologists monitor the safety of brominated esters like methyl 2-bromohexanoate closely. Animal studies highlight moderate acute oral toxicity, prompting strict handling protocols to limit accidental ingestion. Research into bioaccumulation and metabolic breakdown in environmental systems guides disposal processes and regulatory frameworks. Professional experience teaches us that careless disposal into wastewater systems leads to persistence in the environment, so labs and manufacturing firms commit resources to proper waste treatment. Companies often share safety information as part of supply chain responsibility, helping end users recognize potential hazards early in the process.
Future Prospects
The future of methyl 2-bromohexanoate blends advances in chemistry with increasing demands for safety and sustainability. Synthetic chemists continue designing new derivatives for pharmaceuticals and advanced materials, with the ester’s core structure at the center of their work. The movement toward greener chemistry practices favors routes with lower waste and safer reagents, so process improvements that cut out hazardous solvents and minimize byproducts enjoy a premium. Based on recent patents and publications, interest in broader biological testing and emerging applications signals long-term relevance for this molecule. Technical teams across disciplines see methyl 2-bromohexanoate not as a relic of mid-century organic chemistry, but as a springboard for next-generation discoveries.
The Basics of Methyl 2-Bromohexanoate
Methyl 2-Bromohexanoate comes up in many synthetic chemistry labs. This compound plays a part in research and fine chemical production. Its value owes much to bromine’s behavior in organic chemistry, where it helps tailor molecules with precision.
Chemical Formula Explained
Methyl 2-Bromohexanoate has the chemical formula C7H13BrO2. If you break that down, the skeleton comes from hexanoic acid—a six-carbon chain. At the second carbon, a bromine atom swaps in for one hydrogen. Then methylation on the carboxylic acid side gives the ester. The full breakdown: seven carbon atoms, thirteen hydrogens, one bromine, and two oxygens.
This structure isn’t just an academic trivia point. The placement of the bromine atom gives it special reactivity, which can be leveraged for all kinds of next steps in synthesis. It stands ready for nucleophilic substitution or further transformations. Chemists building blocks for pharmaceuticals, agricultural products, or new materials appreciate these versatile features.
Practical Experience with Chemical Synthesis
I’ve worked with halogenated esters in graduate research, and caution always followed. Reactivity can be a double-edged sword: efficiency in one stage, hazards in the next. Methyl 2-Bromohexanoate can irritate the skin and eyes, and the bromine’s presence means waste requires careful disposal. In my own bench work, I learned to keep all personal protective equipment handy—goggles, gloves, and solid ventilation. Mishaps aren’t abstract in a lab. One colleague once underestimated halogenated solvents, and a small splash led to hours at the eye-wash. Lessons stick deep after you face them up close.
Handling reagents like this shines a light on the need for clear protocols and regular training. Industry statistics reveal chemical accidents happen mostly when people rush, improvise, or cut corners on safety. The U.S. Chemical Safety Board reports routine laboratory incidents for a reason. Institutions and companies must give staff time and resources for safety culture—not just compliance on paper.
Environmental and Regulatory Considerations
Building blocks like Methyl 2-Bromohexanoate feed into larger chains of production. Proper storage and handling help prevent contamination and limit risks for workers and the environment. Brominated chemicals have a history of persistence if they reach water or soil. Waste streams with bromine must be neutralized and tracked.
Regulations keep a close eye on halogenated compounds, especially where disposal comes into play. Facilities using these chemicals must adopt filtering, incineration, and other mitigation steps. These efforts pay off: regions with strict hazardous waste rules report fewer contamination incidents per capita and improved water quality, according to EPA summaries.
Building Toward Better Solutions
Safer chemistry remains a team sport. At the research level, some labs experiment with greener, less hazardous alternatives. Chemists tweak molecules to swap out bromine, relying instead on bio-based or biodegradable groups. The conversation shifts—away from only making useful molecules, toward designing them with minimal footprint from start to finish. This takes time, collaboration, and investment in both training and updating protocols.
Each time a scientist chooses, handles, and discards a reagent like Methyl 2-Bromohexanoate responsibly, the benefits ripple further—past one lab, past one project, reinforcing standards across the field.
What Makes Methyl 2-Bromohexanoate Stand Out?
Factories don’t run on stories—they run on chemistry. Methyl 2-bromohexanoate shows up in labs where practical work gets done, not just theory. It’s a clear, colorless liquid, and chemists in pharmaceuticals, agrochemicals, and specialty materials have relied on it. My years working with research teams have shown me that this compound can change the pace of a project from slow and steady to fast-tracked. It’s not just another name on a list. It sits in storage cabinets for a good reason.
Pharmaceutical Syntheses
This compound forms the backbone of building blocks in the drug world. Scientists often reach for it during the design of new molecules, searching for better medicines. Methyl 2-bromohexanoate acts as an alkylating agent. That means it attaches pieces to other molecules in ways that are hard to do with less reactive chemicals. At one generic drug firm, I’ve seen teams use it to build up the carbon skeletons of antiviral and pain medication candidates. It’s rarely the star but often the reliable set tool. Its reactivity gives chemists creative space to tweak and perfect their designs.
Agrochemical Pathways
Fields and crops all over depend on safe, potent compounds. Research into new herbicides and insecticides often circles back to core intermediates, and here’s where this molecule fits in. My agricultural contacts tell me they look to methyl 2-bromohexanoate when trying to fine-tune pesticides. This molecule provides a handy starting point for molecules that scare away pests or kill weeds. It helps create structures that encourage selectivity, so treatments target the intended pest, not everything in the field.
Tool for Organic Synthesis
Every chemist has a set of trusted reagents. Methyl 2-bromohexanoate belongs in this set when building fine chemicals. Its value lies in how it brings together two pieces of a molecule quickly, thanks to its bromo group. Synthetic chemists use it to introduce functional groups—parts that make a molecule do what you want. In my lab days, I’ve seen it used in Grignard reactions and nucleophilic substitutions, giving rise to everything from specialty lubricants to flavor compounds. This saves time, reduces waste, and lets projects adapt to change.
Industry Needs and Safety
Handling this compound needs experience. It’s reactive and can be dangerous without respect for good lab practices. Wearing gloves and eye protection becomes a habit, not a suggestion. On the industrial scale, engineers design special containment and ventilation for processes using methyl 2-bromohexanoate. This protects both workers and the environment. Green chemistry movements have begun encouraging streamlined processes and improved waste handling.
Paths Toward Sustainability
Few things matter more to me than practical, real-world improvement. Advances in catalysis and reaction design aim to reduce waste and energy use for molecules like this one. Academic labs and industry teams keep searching for alternative reagents and safer, easier processes. Some firms recycle solvents and capture byproducts to cut down on the mess—less time, fewer resources, a safer planet.
Final Thoughts on Its Importance
Chemistry rarely moves forward without compounds like methyl 2-bromohexanoate. Whether it’s a new drug, an efficient insecticide, or a clever solution on the bench, this molecule gets the work done. With care, training, and thoughtful innovation, it’ll remain a backbone of synthetic chemistry for years.
Why Precautions Matter in the Lab
Methyl 2-Bromohexanoate looks clear and innocuous in a bottle, but anyone who’s worked with it in a lab knows the reality. This compound packs a punch. It won’t explode at a glance, but take a casual approach and the day can go sideways. So, it’s worth talking through what I’ve learned about treating this chemical with the respect it deserves, how seasoned chemists keep accidents at bay, and why those safety rules deserve more than just a quick glance.
The Drip Pan and The Backup
Corrosive chemicals seldom advertise their risk until it’s too late. Methyl 2-Bromohexanoate has a knack for creeping out of loose caps and giving off fumes that sting the nose and eyes. The simplest fix is basic: keep the bottle tightly closed and store it in a well-ventilated space. On my first run-in, I tucked it behind a fume hood sash and soon realized this spot saved much grief—no surprise leaks or smells, just steady airflow and protection from sunlight. Light can degrade the compound, so dark glass bottles are a smart upgrade. Best practice: label everything in bold, waterproof ink so there’s no confusion during a busy shift.
Gloves Aren’t Just a Nice Touch
I hear folks say nitrile gloves are fine for “most” chemicals. Methyl 2-Bromohexanoate doesn’t forgive shortcuts. Even tiny skin exposure causes irritation for plenty of people. I’ve learned to double up with long-cuffed gloves and change them after each use, even if that feels tedious. Lab coats matter, too—one splash on your regular shirt and you’ll be itching for days. I always add goggles and sometimes a face shield, especially if pouring larger amounts. It’s not about fear; it’s about knowing my skin won’t thank me for rolling the dice.
Never Alone, Never Rushed
Experience in the lab teaches the value of pace and preparation. Distractions sneak up fast, but working with methyl 2-bromohexanoate distracted means bumping into spilled drops or letting the vapor get to you. I make it a rule to lay out all tools before uncapping the bottle, and never, ever work with this solvent alone. Problems come up, so it helps having backup who knows what to do if something tips over or goes wrong.
Disposal and Spills: Fast, Not Careless
Waste management brings out the worst in lazy habits. Once, I saw someone pour a leftover amount down the sink. The smell alone told us this wasn’t water-safe, and the drain pipes threatened to corrode. We learned to seal all liquid waste in chemical-resistant containers and label them for proper collection. Small spills get handled fast with an absorbent pad and a tight-lidded waste jar nearby. Every lab should keep calcium carbonate or similar neutralizer close at hand, with easy instructions right on the wall.
Training, Not Just Paperwork
Many folks breeze through paperwork on safety. It pays to see hazard training as real preparation, not just a formality. Newcomers should watch old hands handle the compound and rehearse emergency drills, not just read checklists. I’d argue labs run safer when everyone refreshes their skills and shares close calls, even the embarrassing ones.
Keep It Simple, Stay Safe
The rules for storing and handling methyl 2-bromohexanoate boil down to solid habits: seal it tight, shield it from light, protect your skin, and act fast if things go wrong. Every bottle is a reminder that lab safety rests on sweat, vigilance, and the willingness to learn from each new day in the lab.
Looking Closer at the Numbers
Walk into any lab with a bottle of Methyl 2-Bromohexanoate and the first real question isn’t how much you have. It’s about how much each molecule weighs. This compound, with the formula C7H13BrO2, clocks in at a molecular weight of 225.08 grams per mole. That may seem like simple trivia, but in my days wrangling reagents in organic synthesis, that number mattered every single time a pipette came out.
Think back to the dozens of times you’ve measured out reagents on a balance. Without knowing the precise molecular weight, every calculation about amounts turns into guesswork. Small errors start to creep in, and soon—for something as sensitive as a bromoester—you might find your reaction yield dropping or even a side product you never planned for.
Understanding Why This Weight Matters
I remember a project in a small academic lab early in my career. We tried to scale up a reaction that used Methyl 2-Bromohexanoate as a key intermediate in a drug discovery pathway. Our calculations needed to be spot on. Just a half a gram over or under, and our entire batch’s stoichiometry fell apart. That affected time spent troubleshooting, wasted solvents, and sometimes a cramped deadline looming on our shoulders.
The molecular weight links theory with practice. I’ve seen well-designed experiments go sideways because someone trusted a value from a questionable catalog listing. Double-checking those numbers—especially for compounds with halogens, like bromine here—becomes second-nature when you work with sensitive reactions. Bromine itself weighs in at about 79.9 g/mol, much heavier than carbon, hydrogen, or oxygen, so even a small miscount in atoms warps the math.
Quality, Sourcing, and Safety
In my own sourcing, reputable suppliers and solid chemical catalogs proved themselves by backing up their values with data sheets and spectroscopy. Some offer QR codes linked to NMR data or historical references. A consistent, confirmed molecular weight doesn’t just help with reactions. It keeps you honest with regulatory paperwork and safety documentation. Methyl 2-Bromohexanoate isn’t just a number. It’s a flammable liquid with health risks, so accurate calculations help prevent both process errors and safety slip-ups.
Academic and industrial chemists both keep molecular weights in their toolbox—not as trivia, but as a fundamental fact shaping every aspect of their work. Without it, clarity and reproducibility fade quickly. The widespread adoption of electronic lab notebooks, automatic balances, and chemical procurement systems hasn’t changed that need for accuracy; it’s just made it easier to keep everyone on the same page. I’ve found that a mistake caught by a careful chemist saves not only materials, but trust and reputation inside a team or company.
How to Keep Errors in Check
Making sure you have the right number involves a few habits that never grow old. Double-check with a secondary source. During batch prep, make it standard to revisit both the catalog and the SDS. Peer review among colleagues—an easy chat over a bench—often catches mistakes a tired pair of eyes could overlook. Adopting verification by analytical methods, like mass spectrometry or combustion analysis, brings certainty to your workflow.
In the end, the molecular weight of Methyl 2-Bromohexanoate—225.08 g/mol—serves as both a mathematical anchor and a safeguard. From batch records to regulatory support, it’s proof that chemistry rewards careful attention to the smallest details.
The Chemical at a Glance
Methyl 2-Bromohexanoate doesn’t show up in the usual headlines or spark much debate outside the science community. It looks harmless enough: a clear or pale yellow liquid, usually known to people working in labs, research, or chemical manufacturing. This compound often acts as a building block in the world of organic chemistry. Its uses stretch from synthesizing pharmaceuticals to specialty chemicals. I’ve seen bottles of this in some lab storerooms — stashed away with all sorts of warning labels. Those warnings catch the eye for a reason.
Health Concerns
I’ve spent time in labs where chemicals travel from shelf to experiment, and it’s impossible to overstate how essential safety is. Methyl 2-Bromohexanoate brings a few notable risks. It gives off fumes that irritate the skin and eyes, and the throat gets a scratch if the stuff hangs in the air. People with asthma or chronic lung problems can find conditions worsened by exposure to even a small leak or accidental spill. There’s not much in public databases about cancer risk, but brominated compounds sometimes link to chronic toxicity and can trigger allergic reactions.
Direct contact with this chemical leaves a real sting. A drop on open skin or a splash in the eye demands emergency washing. Sometimes, folks who don’t wear gloves or goggles, maybe because they’re distracted or think the job will just take a second, end up in trouble. In poorly ventilated rooms, just inhaling the vapor can knock your lungs for a loop.
Environmental Impact
Methyl 2-Bromohexanoate doesn’t just vanish when a bottle tips or a pipe leaks. If it slips down the drain or seeps into soil, the environment gets the burden. Brominated organics stick around longer than most want in surface water, potentially harming aquatic life. Some research highlights that this group of chemicals can pile up in the fat of fish. If the trend continues, the food chain faces contamination. I’ve spoken with environmental scientists who worry about these “forever” compounds lingering, disrupting natural cycles far from any lab.
Few regulations specifically address this chemical, but local spill rules usually apply. Municipal treatment plants can have trouble breaking down molecules like this one, increasing the chance of runoff that pollutes streams, rivers, and groundwater. Poor management doesn’t just affect wildlife; drinking water in nearby communities can carry unsafe traces.
Fact-Based Steps to Reduce Harm
Most dangers from Methyl 2-Bromohexanoate fall off sharply with proper handling. Chemical goggles, neoprene gloves, and tight-fitting masks are a must in any setting where the liquid gets transferred, mixed, or heated. Schools and factories that train workers properly see fewer accidents, based on OSHA data.
Labs should invest in spill-proof containers and vented storage cabinets. Disposal gets tricky: simply washing it down the drain absolutely counts as risky behavior. Working with an industrial hazardous waste partner reduces the odds of contamination. I’ve found that companies who take environmental audits seriously often tweak workflows so that accidental releases almost never happen.
Responsible Use
People who spend time around Methyl 2-Bromohexanoate need to respect its power. Stay mindful of both workplace and environmental health, keep exposure as low as possible, and use PPE that does its job. Community officials, regulators, and industry managers share responsibility for safe stewardship. Strong training, airtight protocols, and thoughtful chemical storage help keep this compound from crossing the line from helpful ingredient to hazardous mess.
| Names | |
| Preferred IUPAC name | Methyl 2-bromohexanoate |
| Other names |
2-Bromohexanoic acid methyl ester
Methyl 2-bromohexanoate Methyl alpha-bromohexanoate NSC 13980 |
| Pronunciation | /ˈmɛθɪl ˈtuː ˌbroʊmoʊ hɛkˈseɪnoʊ.eɪt/ |
| Identifiers | |
| CAS Number | 6299-43-4 |
| 3D model (JSmol) | `CCCC(Br)CC(=O)OC` |
| Beilstein Reference | 1221580 |
| ChEBI | CHEBI:18783 |
| ChEMBL | CHEMBL274688 |
| ChemSpider | 24663445 |
| DrugBank | DB08397 |
| ECHA InfoCard | 03-2119941333-49-0000 |
| EC Number | 68141-06-2 |
| Gmelin Reference | 1531344 |
| KEGG | C14160 |
| MeSH | Methyl 2-bromohexanoate |
| PubChem CID | 1201434 |
| RTECS number | MO9625000 |
| UNII | W2H1C570GR |
| UN number | UN3272 |
| CompTox Dashboard (EPA) | DTXSID7024369 |
| Properties | |
| Chemical formula | C7H13BrO2 |
| Molar mass | 209.09 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Density | 1.320 g/cm³ |
| Solubility in water | Insoluble in water |
| log P | 1.99 |
| Vapor pressure | 0.133 mmHg (25°C) |
| Acidity (pKa) | pKa ≈ 25 |
| Magnetic susceptibility (χ) | -6.85 × 10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.4560 |
| Viscosity | 1.366 cP (25°C) |
| Dipole moment | 2.60 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 416.6 J/mol·K |
| Pharmacology | |
| ATC code | |
| Hazards | |
| GHS labelling | GHS02, GHS07 |
| Pictograms | GHS07 |
| Signal word | Warning |
| Hazard statements | H315, H319, H335 |
| Precautionary statements | P261, P264, P271, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P403+P233, P405, P501 |
| Flash point | 82.2 °C |
| Lethal dose or concentration | LD50 (oral, rat) > 2000 mg/kg |
| NIOSH | Not established |
| PEL (Permissible) | No PEL established. |
| REL (Recommended) | 10 mg |
| IDLH (Immediate danger) | Not established |
| Related compounds | |
| Related compounds |
Ethyl 2-Bromohexanoate
Methyl 2-Bromobutanoate Methyl 2-Bromo-4-methylpentanoate Methyl 2-Bromoheptanoate Methyl 2-Bromopropanoate |
