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Ethyl 3-Bromo-2-Oxobutyrate

    • Product Name Ethyl 3-Bromo-2-Oxobutyrate
    • Alias Ethyl 3-bromoacetoacetate
    • Einecs EINECS 244-464-0
    • Mininmum Order 1 g
    • Factory Site Tengfei Creation Center,55 Jiangjun Avenue, Jiangning District,Nanjing
    • Price Inquiry admin@sinochem-nanjing.com
    • Manufacturer Sinochem Nanjing Corporation
    • CONTACT NOW
    VTB
    Specifications

    HS Code

    561807

    Name Ethyl 3-Bromo-2-Oxobutyrate
    Cas Number 814-78-8
    Molecular Formula C6H9BrO3
    Molecular Weight 209.04 g/mol
    Appearance Colorless to pale yellow liquid
    Boiling Point 77-80 °C at 11 mmHg
    Density 1.496 g/mL at 25 °C
    Melting Point -14 °C
    Refractive Index 1.460-1.465
    Purity Typically ≥ 97%
    Solubility Soluble in organic solvents (e.g., ether, chloroform)
    Flash Point 86 °C
    Synonyms Ethyl 3-bromoacetoacetate
    Storage Temperature 2-8 °C
    Smiles CCOC(=O)CC(Br)=O

    As an accredited Ethyl 3-Bromo-2-Oxobutyrate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

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    Application of Ethyl 3-Bromo-2-Oxobutyrate

    Applications of Ethyl 3-Bromo-2-Oxobutyrate in Industrial Manufacturing

    As a direct manufacturer of Ethyl 3-Bromo-2-Oxobutyrate, we focus on high-value intermediates supplied into industrial production lines across several established chemical sectors. The following precise application scenarios reflect commercial practices currently utilizing this specialty compound, each with their operational specifications, regulatory mandates, and integration details tailored to downstream process needs.

    1. Pharmaceutical Intermediates for Cephalosporin Antibiotic Synthesis

    Ethyl 3-Bromo-2-Oxobutyrate serves as a core acylating agent in the synthesis pathway of cephem nucleus intermediates widely used in cephalosporin antibiotic manufacturing. Drug producers employ this raw material to introduce a reactive bromo group, facilitating high-yield, stereospecific construction of side chains on β-lactam cores. The stage-specific addition carefully balances bromination and stability for controlled conversion, and the use of this product is documented in GMP-compliant active pharmaceutical ingredient (API) supply chains.

    Industry compliance standards

    • ICH Q7 Good Manufacturing Practice for Active Pharmaceutical Ingredients
    • EU GMP Guidelines Part II for pharmaceutical intermediates
    • US FDA 21 CFR Part 211 for finished pharmaceuticals
    • Chinese Pharmacopoeia, monographs on API synthesis quality and impurity profiling

    Typical usage ratio

    • 0.6 to 1.1 molar equivalents in relation to aminothiazole substrates; the ratio varies with desired regioselectivity during side-chain coupling reactions

    Downstream process integration

    • Charged during the acylation step following deprotection of the aminothiazole ring; involves low-temperature addition under inert atmosphere to minimize by-product formation

    Final product types

    • 7-ACA intermediates for cephalosporin production
    • Cephalosporin semi-synthetic antibiotics (e.g., cefuroxime axetil, cefotaxime)
    • Pharmaceutical-grade cephalosporin intermediates exported under regulated supply agreements

    2. Agrochemical Intermediate in Pyrrole and Pyrazole Herbicide Synthesis

    Crop protection formulators rely on this compound as a precursor during the construction of pyrrole and pyrazole scaffolds, which form the backbone of several patented herbicides. The unique bromo functional group enables selective ring substitution and further functionalization, contributing directly to the bioactivity of downstream actives. Use at this stage must comply with agrochemical intermediate handling standards to support downstream registration for use on food crops.

    Industry compliance standards

    • FAO/WHO Technical Guidelines for the Registration of Agrochemicals
    • OECD Guidelines for the Testing of Chemicals (GLP requirements for process residues)
    • China GB 2763 MRL Standards (for final product) – upstream producers must provide residue testing support
    • ISO 9001:2015 quality management for chemical manufacturing

    Typical usage ratio

    • 0.8–1.2 equivalents based on nucleophilic substrate; the ratio aligns with batch size and ring formation selectivity, adjusted for impurity minimization

    Downstream process integration

    • Added after diazotization of precursor for halogenated ring functionalization; bromination conducted under controlled temperature range (0–5°C) to control exotherm and by-products

    Final product types

    • Selective herbicide actives (e.g., pyrazole-derived weed inhibitors)
    • Pyrrole-based soil sterilants
    • Bulk agrochemical intermediates supplied to global formulators

    3. Fine Chemical Synthesis for Flavors and Fragrance Intermediates

    Specialty chemical producers employ Ethyl 3-Bromo-2-Oxobutyrate in the creation of bromoacetyl derivatives used as key intermediates for high-purity flavor and fragrance ingredients, such as aldehydes and ketones that form the aroma profile of consumer products. Strict control during handling and formulation preserves olfactory purity and trace impurity levels for IFRA-compliant ingredients.

    Industry compliance standards

    • IFRA (International Fragrance Association) Code of Practice
    • ISO 9235:2013 for natural and synthetic aroma chemicals
    • HACCP certification when used in food-contact flavors
    • EU Regulation (EC) No 1334/2008 for flavoring substances

    Typical usage ratio

    • 0.9–1.05 molar equivalents per esterification step, with fine adjustments based on fragrance compound chain length and purity

    Downstream process integration

    • Incorporated during initial acylation of aromatic alcohol precursors; typically processed in batch reactors with close monitoring of residual bromide and elimination of by-products via distillation

    Final product types

    • Bromo-derived fragrance aldehydes (e.g., bromoacetophenone derivatives)
    • Ketone-based flavoring ingredients for beverages and confectionery
    • Intermediates for fragrance houses supplying to global cosmetics brands

    4. Pharmaceutical Intermediate for Synthesis of α-Keto Ester Building Blocks

    API manufacturers integrate this compound in the early-phase assembly of α-keto esters, taking advantage of the bromo group’s reactivity for downstream C–C and C–N bond formation. These building blocks play a pivotal role in the synthesis of antiviral, antifungal, and anti-inflammatory drug candidates. Production lines require validated processing to conform to quality and impurity requirements for further pharmaceutical conversion.

    Industry compliance standards

    • USP-NF General Chapters on Pharmaceutical Intermediates
    • ICH Q3A/B for impurities profiling in APIs
    • EU Pharmacopoeia requirements for chemical purity
    • ISO 9001:2015 certified production management

    Typical usage ratio

    • 0.7–1.0 equivalent in Michael addition and acetoacetate functionalization; dosage is selected based on target substrate’s reactivity and final application

    Downstream process integration

    • Reacted directly with amine/aryl-containing synthons during α-functionalization; steps generally run under reflux in polar solvents to promote complete conversion and easy work-up

    Final product types

    • α-Keto ester pharmaceutical intermediates
    • Drug candidate precursors for antiviral and anti-inflammatory compounds
    • Component blocks for chiral catalyst production in pharmaceutical synthesis

    5. Key Intermediate in Dye and Pigment Manufacturing (Thiazole Dye Precursors)

    Dye manufacturers employ Ethyl 3-Bromo-2-Oxobutyrate in the preparation of thiazole and benzothiazole-based dye precursors, where its reactive bromo group enables direct integration into heterocyclic chromophores. Batch production must comply with stringent quality and residual halogen content, as these parameters directly impact the stability and performance in textile and printing inks.

    Industry compliance standards

    • OEKO-TEX Standard 100 (for controlled halogen content)
    • REACH Regulation (EC) No 1907/2006
    • GHS Classification and Labeling requirements
    • ISO 14001 for environmental management relevant to dye production

    Typical usage ratio

    • 1.0–1.3 molar equivalents, adjusted to maintain high conversion rates in heterocyclic cyclization and minimize unreacted starting material

    Downstream process integration

    • Incorporated during condensation with amines or thiols; typically heated to moderate temperatures in polar aprotic solvents for maximum yield of thiazole intermediates

    Final product types

    • Thiazole dye and pigment intermediates
    • Colorants for textile, leather, and ink applications
    • Specialty dyes used in electronic device manufacturing
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    More Introduction

    Discovering the Value of Ethyl 3-Bromo-2-Oxobutyrate

    Unlocking New Possibilities in Organic Synthesis

    It’s easy to scroll past a chemical name as unremarkable as ethyl 3-bromo-2-oxobutyrate. Yet for anyone who appreciates the hidden power of simple molecules in the modern lab, even a quick glance at this compound says volumes about its versatility. Ethyl 3-bromo-2-oxobutyrate, drawing from the trusted structure of beta-keto esters, brings together a reactive bromine with a classic butyrate backbone. Chemists handling synthetic pathways spot new possibilities the moment this reagent hits the bench.

    Putting Structure to Work

    At its core, the model of ethyl 3-bromo-2-oxobutyrate is straightforward but never boring: it contains a bromine atom fixed at the third carbon of a four-carbon skeleton with a keto group at position two and an ethyl ester finishing the chain. Nothing unnecessary weighs it down. Those who experiment with it recognize how this clean structure allows for smooth entry into acylation, alkylation, and substitution reactions.

    If you spend much time poring over synthesis papers or squinting at glassware, you know certain reagents become favorites for a reason. Ethyl 3-bromo-2-oxobutyrate delivers stable performance in established reactions, especially where careful control over substitution and rearrangement is important. Reactions demanding selectivity and reliability, like the construction of elaborate carbon skeletons or the introduction of alternative functional groups, benefit from this molecule’s personality: neat, manageable, not quick to decompose.

    Why It Matters for Industry and Research

    This compound’s draw comes from its balance of reactivity and manageability. Where many halogenated compounds suffer from volatility or troublesome byproducts, ethyl 3-bromo-2-oxobutyrate avoids these pitfalls. Synthesis teams, whether working on pharmaceuticals, agrochemical leads, or advanced materials, reach for tools that don’t add unnecessary variables or headaches. In processes that call for the formation of substituted acetoacetate esters or the preparation of alpha-bromo derivatives, this chemical stands up to rigorous handling and scale-up.

    One notable use involves the formation of new carbon-carbon bonds. The bromine group sitting three atoms away from the carbonyl oxygen sets up a scene ready for nucleophilic attack, opening the door to create more complex esters, acids, and even heterocycles. Personal experience and the stack of reaction schemes in many published protocols suggest this reagent is a workhorse for making building blocks that later enter medicines or performance materials.

    How It Compares to Related Reagents

    There’s plenty of competition in the world of halogenated butyrate esters and alpha-bromo keto compounds. Those who have handled 3-chloro or 3-iodo analogues quickly spot the differences: bromine strikes a balance between the strong leaving ability of iodine and the greater stability (sometimes sluggishness) of chlorine. The bromo group detaches at a steady pace—not so fast that reactions spin out of control, not so slow that work grinds to a halt. Synthetic campaigns count on that reliability.

    Looking at usability, some halogenated esters ask for extra caution or special ventilation setups to deal with fumes or unstable byproducts. Ethyl 3-bromo-2-oxobutyrate carries a manageable safety profile. Good lab technique—use of gloves, eye protection, and respect for chemical handling—is usually enough for its routine use. Making a choice between the bromo and chloro forms often comes down to whether you want easier displacement or more persistence under reaction conditions.

    Ethyl acetoacetate and unhalogenated esters also enter these discussions. For making direct acylations or simple transesterifications, you might pick an unhalogenated version. The real advantage of ethyl 3-bromo-2-oxobutyrate lies in its ability to introduce new substituents at precisely the right site, no extra steps required. Synthesis can be much shorter and cleaner when a strategic halogen makes the difference between a five-step detour and a single, direct transformation.

    Impacts in the Laboratory

    Any chemist who spends time in organic synthesis knows the frustration of unpredictable reagents: failed reactions, unexpected side-products, time wasted with purification. Over years spent running both small and multi-gram reactions, patterns emerge. The best tools tend to be the simplest, the most reliable, and the least likely to introduce unknowns. Ethyl 3-bromo-2-oxobutyrate belongs to that group. Repeat runs confirm it holds up on the bench, keeps its purity intact in cold storage, and doesn’t force researchers to chase after strange byproducts.

    Some of the worst days in the lab come when a synthesis that worked at the milligram scale explodes with impurities at larger volumes. You spend more hours at the column than at your own desk. Occasionally, halogenated reagents fuel those nightmares. With ethyl 3-bromo-2-oxobutyrate, scaled-up efforts for grams instead of milligrams don’t come with those hidden risks. Documented work supports this: groups reporting their use in medicinal chemistry campaigns see yields stay consistent and purification steps remain manageable. In practice, this means less wasted material and more dependable results, which matters enormously when expensive starting materials and precious time are at stake.

    Pathways and Transformations

    What allows ethyl 3-bromo-2-oxobutyrate to take on so many roles? The answer lies in its structure as well as experience from real projects. By placing a reactive bromo group in the beta position relative to both the ester and the keto group, chemists access a broad palette of transformations. For nucleophilic substitution, the carbon attached to bromine opens to a wide range of reactants: amines, oxygen-based nucleophiles, even certain sulfur compounds. That means rapid access to a library of new molecules, fitting neatly into larger projects aimed at lead optimization or functional material discovery.

    In practice, I’ve seen this compound shine in coupling reactions that make otherwise challenging skeletons possible. It steps into ring-forming reactions, leading to new heterocycles and bioactive frameworks. Its relative stability means that the product mixtures contain fewer surprises—even after heating or stirring for hours. Many researchers value this predictability, especially in multi-step syntheses where every decision compounds downstream complexity.

    When pressed for versatility, ethyl 3-bromo-2-oxobutyrate proves capable. It can act as a starting material for alpha-carbonyl alkylations, contributing to both lab research and the early stages of commercial process development. The literature backs up these uses, with reports ranging from anti-inflammatory pharmaceutical building blocks to polymerizable monomers. Such breadth ensures this compound earns space on the shelf for new and ongoing projects.

    Reflections From the Bench

    With years spent around fume hoods and glassware, it’s clear certain chemicals quietly earn an outsized respect. Not because they claim the spotlight with exotic names, but because they deliver, time and again, in both routine and ambitious procedures. Ethyl 3-bromo-2-oxobutyrate is one of those molecules. It rewards careful planning and execution without demanding constant troubleshooting.

    Some products tempt users with novel features, but wind up tangled in handling issues or difficult compatibilities. This compound rarely asks for more than standard precautions—no need for extreme refrigeration or elaborate wrappers to protect it from ambient light. You walk into the stockroom, select your bottle, and trust that methodical weighing and addition will produce the expected results.

    Over multiple projects, I’ve turned to ethyl 3-bromo-2-oxobutyrate whenever pathways require fast functionalization. It functions as both a trusted solution and a flexible building block—one that slots easily into established methods and is adaptable enough for creative assembly. That’s an underappreciated value in a research culture where shortcuts rarely exist and reliability means everything.

    Sourcing and Quality

    Navigating the world of chemical supply often means sorting through products of variable purity and consistency. For researchers and process chemists, it’s not enough to have the right compound on paper; what arrives in the bottle must match the label both in identity and purity. Ethyl 3-bromo-2-oxobutyrate is commonly available with high specification, above ninety-eight percent purity, which protects against side reactions that can trip up careful synthesis.

    Regular checks—NMR, GC, and mass spec—confirm the product entering critical reactions holds up across batches. And as colleagues in both academic and commercial settings will attest, a reliable supplier relationship removes a major source of experimental variability. Nobody enjoys tracking down odd results only to realize a single impurity in a key reagent is to blame.

    For larger-scale work, the consistency of ethyl 3-bromo-2-oxobutyrate across kilogram quantities means development teams feel confident progressing from lab to pilot scale, knowing that reaction yields and selectivities remain constant. Such predictability translates directly into reduced waste, streamlined documentation, and easier regulatory sign-off when needed.

    Addressing Drawbacks and Challenges

    Like any reactive halogenated compound, ethyl 3-bromo-2-oxobutyrate requires some mindfulness in handling and waste management. Even though it doesn’t top toxicity charts, safe disposal practices still deserve attention. Exposing waste streams to excess nucleophiles or reducing agents—standard practice—helps deactivate bromo compounds before they head for waste treatment.

    Storage conditions remain pretty basic: a cool, dry place and a caped bottle keep the product stable over long periods. In the rare event of decomposition or contamination, the breakdown is usually obvious due to color change or altered odor. Regular inventory rotation guards against unexpected degradation.

    Reactivity with strong nucleophiles sometimes asks for slower addition or careful monitoring to prevent excess heat or product decomposition. With a little planning, these risks don’t overshadow the benefits, but attention to bench safety pays dividends. Many labs appreciate specialist waste bottles for halogenated organics, further assuring safe and compliant waste management.

    Building a Reliable Chemistry Ecosystem

    A working research group, whether in academia or industry, thrives on dependable tools and honest conversations about what works. Ethyl 3-bromo-2-oxobutyrate has earned its place by doing the job, staying stable in normal conditions, and offering multiple avenues for creative synthesis. More than once, I’ve seen it make the difference between a stalled route and a surprising breakthrough in complexity or yield.

    In research, the most subtle improvements can make outsized impacts: a shortcut saves weeks, a single, robust intermediate opens new avenues for exploration, and a dependable reagent keeps costs and timelines under control. With the rising demand for faster, cleaner, and more adaptive synthesis, molecules like ethyl 3-bromo-2-oxobutyrate take on new importance.

    Working in collaboration with quality assurance teams and supply partners also strengthens the chain of reliability. Transparent paperwork, confirmed analysis, and well-documented storage procedures build trust along the entire supply route. This reduces the kind of experimental ambiguity that slows scientific progress and drains morale.

    Potential Solutions to Emerging Barriers

    With environmental and regulatory scrutiny growing each year, chemists face rising pressure to minimize waste and choose safer chemicals. Here, iterative improvement, not replacement, often makes the biggest impact. Finding ways to recover, recycle, or neutralize halogen content in spent residues is no longer just a best practice, but a responsibility. Luckily, the effective use and containment of ethyl 3-bromo-2-oxobutyrate fit well with these evolving standards.

    Forward-thinking labs adopt green chemistry principles by weighing alternatives, improving atom economy, and integrating selective reaction conditions that use milder bases or solvents. For teams scaling up processes, closed loops that capture offgas or recover reusable solvents help shrink the environmental footprint. Documenting every improvement shows practical progress for audits and aligns with societal expectations.

    Education—both for newcomers and seasoned staff—remains key. Onboarding protocols that include specific training around halogenated reagent risks anchor a culture of safety. Integrating best practices across organizations raises the baseline for everyone. Accessible resources, clear signage, and open dialogue all have their roles in keeping daily work both productive and responsible.

    The Science Behind Everyday Impact

    If the progress of organic chemistry owes much to quietly reliable reagents, ethyl 3-bromo-2-oxobutyrate deserves more recognition among them. Whether assembling drug candidates, building bioactive scaffolds, or creating functional polymers, this molecule underpins transformation after transformation, linking simple steps into complex products.

    The wave of innovation sweeping through medicine and technology often begins with modest bottles like these. Real experience shows that while no single reagent makes breakthroughs alone, dependable building blocks multiply options and lower technical barriers. As new projects call for bolder and faster synthesis, tools proven to perform under many conditions become crucial assets.

    For all its simplicity, the story of ethyl 3-bromo-2-oxobutyrate reminds us: chemistry’s progress marches on the shoulders of both discovery and dependability. It stands as a case study in how understanding a chemical’s unique features, treating it with care, and pushing for continual improvement move research forward—one flask at a time.

    Looking Ahead

    The demand for adaptable chemistry grows stronger as industries push for smarter, more efficient methods. Ethyl 3-bromo-2-oxobutyrate, by virtue of its proven track record and inherent strengths, offers a launchpad for advances not only in substances synthesized but in how teams approach safety, sustainability, and quality. More chemists are building protocols that rely on well-understood reactions and intermediates, bringing robustness to developing fields and streamlining complex projects.

    As laboratories and companies grow more interconnected worldwide, the value of trusted compounds multiplies. Ethyl 3-bromo-2-oxobutyrate finds a home in research settings from early-stage medicinal chemistry to materials labs and beyond. It sits at the crossroads where stability meets reactivity, and where a well-placed bromo group continues to empower synthesis both old and new.

    In the everyday decisions made by scientists, choices ripple far beyond the bench: cost, sustainability, and quality of work all depend on the small details that build into big achievements. Ethyl 3-bromo-2-oxobutyrate, through proven application and practical reliability, stands out as a link connecting the promise of organic synthesis to real-world results.