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4-Bromothiophene-3-Carboxylic Acid Methyl Ester

    • Product Name 4-Bromothiophene-3-Carboxylic Acid Methyl Ester
    • Alias Methyl 4-bromothiophene-3-carboxylate
    • Einecs 605-535-7
    • 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
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    Specifications

    HS Code

    914662

    Productname 4-Bromothiophene-3-Carboxylic Acid Methyl Ester
    Casnumber 134279-22-8
    Molecularformula C6H5BrO2S
    Molecularweight 221.07 g/mol
    Appearance Light yellow to brown liquid
    Boilingpoint 309.7 °C at 760 mmHg
    Purity Typically > 97%
    Density 1.670 g/cm3
    Solubility Soluble in organic solvents like DMSO, chloroform
    Smiles COC(=O)C1=CSC(=C1)Br
    Inchi InChI=1S/C6H5BrO2S/c1-9-6(8)4-2-5(7)10-3-4/h2-3H,1H3
    Refractiveindex 1.595
    Storagetemperature Store at 2-8°C
    Synonyms Methyl 4-bromothiophene-3-carboxylate

    As an accredited 4-Bromothiophene-3-Carboxylic Acid Methyl Ester factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

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    Application of 4-Bromothiophene-3-Carboxylic Acid Methyl Ester

    Applications of 4-Bromothiophene-3-Carboxylic Acid Methyl Ester in Industrial Manufacturing

    4-Bromothiophene-3-carboxylic acid methyl ester plays a targeted role as a fine chemical intermediate in several regulated industrial value chains. As a direct manufacturer, we serve downstream sectors that require strict batch consistency, analytical traceability, and material compatibility for advanced synthesis. Below we outline real-world application segments using our product and clarify the process parameters, regulatory frameworks, and integration details for each.

    1. Active Pharmaceutical Ingredient (API) Intermediate in Antiviral Drug Synthesis

    Our material is frequently used as a functionalized building block in the multistep synthesis of thienopyrimidine nucleoside analogs. These scaffolds form the core of several investigational and approved antivirals, particularly for hepatitis B and HIV. The brominated compound introduces a reactive handle, allowing precise cross-coupling and halide exchange reactions under GMP-controlled conditions. Its inclusion supports tight batch specifications, minimizing impurity profiles and facilitating regulatory approvals of API lots destined for clinical or commercial supply.

    Industry compliance standards

    • ICH Q7 Good Manufacturing Practice for Active Pharmaceutical Ingredients
    • USP-NF and Ph. Eur. monograph reference for process validation when applicable
    • 21 CFR Parts 210/211 for pharmaceutical manufacturing controls
    • DMF (US Drug Master File) and CEP (Certificate of Suitability) submission practices

    Typical usage ratio

    • Employed in targeted 1.05–1.2 molar equivalents relative to nucleophilic coupling agents, fine-tuned per synthesis step to optimize yields and minimize residual bromide content for downstream purification

    Downstream process integration

    • Added after initial thiophene formation, just prior to Suzuki–Miyaura or Buchwald–Hartwig cross-coupling in automated or semi-automated API production lines, with in-process QC by HPLC and residual solvent analysis

    Final product types

    • Pharmaceutical grade antiviral nucleoside analogs
    • Thieno[3,2-d]pyrimidine APIs
    • Clinical trial materials and reference standards
    • Commercial finished tablets and capsules incorporating the API

    2. Electronic Chemicals: Organic Semiconductor Monomer Synthesis

    The compound serves as a functionalized monomer precursor in the formulation of high-performance thiophene-based oligomers and polymers for use in organic electronics. Its brominated carboxiesters allow precision in controlled polycondensation or Stille coupling, driving tight polymer structure for applications in organic thin-film transistors (OTFTs) and organic photovoltaic (OPV) devices. Manufacturing lines require high-purity input to meet the stringent electronic-grade specifications and maintain reproducible device characteristics.

    Industry compliance standards

    • SEMI MS8-0708 Specification for Polymers Used in Semiconductor Manufacturing
    • IEC 62899-202 International Electrotechnical Commission standards for printed electronics
    • RoHS Directive (2011/65/EU) for restriction of hazardous substances
    • ISO 9001:2015 quality management system for advanced material manufacturing

    Typical usage ratio

    • Utilized at 0.8–1.3 molar ratio relative to co-monomers, exact value set by the desired chain length, electronic mobility target, and final polymer properties; molar ratios adjusted in pilot batch scaling

    Downstream process integration

    • Reacted in precision-controlled reactors following stringent raw material QC, with in-line GPC monitoring of molecular weight distribution and UV-Vis verification for monomer incorporation rates; introduction typically occurs after thiophene ring functionalization but prior to final polymerization

    Final product types

    • P-type and n-type organic semiconducting polymers
    • Active materials for flexible printed circuits
    • Donor–acceptor copolymers for OPV active layers
    • Precursor solutions for inkjet-printed or spin-coated films in display manufacturing

    3. Agrochemical Intermediate for Fungicide Synthesis

    The compound acts as a key functional intermediate in the construction of thiophene-based fungicidal actives. It allows chemists to introduce site-specific functionality via coupling reactions, forming the central core of advanced crop protection agents, especially those designed for cereal and fruit application. The process chemistry must comply with regional and global agrochemical regulations for precursor traceability and low-level impurity management.

    Industry compliance standards

    • FAO/WHO Joint Meeting on Pesticide Specifications (JMPS)
    • OECD GLP (Good Laboratory Practice) for active substance evaluation
    • REACH Regulation (EC) No 1907/2006 for registration and restriction of chemicals
    • ISO 17025:2017 testing and calibration traceability for batch release analyses

    Typical usage ratio

    • Charged at 1.0–1.15 molar equivalents in condensation/coupling with heterocyclic halides or amine nucleophiles; minor overage permitted to ensure full conversion and minimize carry-through of unreacted bromide in final formulation

    Downstream process integration

    • Introduced after primary backbone assembly, immediately before amide coupling or cyclization stages; process parameters strictly monitored for temperature and pH; subsequent purification steps remove methyl ester by-products before formulation into actives

    Final product types

    • Systemic fungicides for cereals and fruits
    • Crop protection intermediates for registered products
    • Precursor chemicals for patent-protected agroactive substances
    • Technical grade actives for local formulation into wettable powders or EC concentrates

    4. Specialty Dye and Pigment Manufacturing

    This molecule provides site-specific functionality in the custom synthesis of thiophene-derived pigments for high-end inks and specialty coatings. Its utility lies in facilitating electrophilic aromatic substitution and subsequent ring-closure to generate colorants with tailored absorption properties, critical for applications such as security printing, laser marking, and textile dyeing. Manufacturers rely on batch-to-batch reproducibility and low residual halide content.

    Industry compliance standards

    • EN 71-3 Safety of Toys – migration of certain elements (for dyes in consumer products)
    • ISO 2834-1:2006 for printability and color testing of pigment dispersions
    • Registration under REACH for dye intermediates
    • VOCs compliance per regional environmental legislation (e.g., US EPA, EU VOC Directive)

    Typical usage ratio

    • Typically 0.9–1.1 molar equivalents relative to chromophore-forming agents, with process-specific adjustment based on desired pigment intensity and solubility profile; sometimes introduced in a staged feed to control reaction exotherm and color development

    Downstream process integration

    • Fed into synthesis after initial aromatic assembly, reacted under temperature-controlled conditions to facilitate coupling and cyclization, with continuous colorimetric monitoring and post-synthesis purification to achieve pigment purity and stability

    Final product types

    • Specialty organic pigments for automotive coatings and industrial plastics
    • Functional dyes for security printing (banknotes, documents)
    • Textile dyes with enhanced lightfastness
    • Photoluminescent pigments for electronics and optoelectronic devices

    5. Fine Chemical Building Block in Flavor and Fragrance Intermediate Synthesis

    The methyl ester functions as a precursor in the selective construction of sulfur-containing ring systems that serve as intermediates for flavor and fragrance molecules. Its reactivity profile supports mild ester hydrolysis and controlled cyclization, creating unique thiophene derivatives required for high-impact, natural-identical aroma compounds. Manufacturers require low-odor, low-heavymetal input and strict compliance with food additive safety guidelines during formulation.

    Industry compliance standards

    • FEMA GRAS (Generally Recognized As Safe) status for thiophene derivatives (where applicable)
    • US FDA 21 CFR Part 172 (Food Additives Permitted for Direct Addition to Food)
    • IFRA (International Fragrance Association) Code of Practice compliance for fragrance use
    • ISO 9001:2015 for traceable sourcing and processing

    Typical usage ratio

    • 0.5–1.5 equivalents in flavor intermediate synthesis, with ratio modulated for yield versus aroma impact; in fragrance, typically 0.8–1.2 equivalents based on downstream conversion efficiency and targeted molecular structure

    Downstream process integration

    • Hydrolyzed and cyclized after initial thiophene activation, followed by selective oxidation or reduction; quality checks at this stage verify absence of off-odor residues, and subsequent blending with alcohols or esters to achieve the final scent/flavor note

    Final product types

    • Thiophene-based aroma chemicals for fine fragrances and colognes
    • Food flavor enhancers simulating natural roasted or nutty notes
    • Flavor intermediates for beverage and confectionery formulations
    • Functional scent compounds for personal care applications
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    Certification & Compliance
    More Introduction

    Introducing 4-Bromothiophene-3-Carboxylic Acid Methyl Ester: What Sets This Compound Apart

    Broadening Horizons in Chemical Innovation

    Meet 4-Bromothiophene-3-Carboxylic Acid Methyl Ester, a compound drawing interest across pharmaceutical, agrochemical, and specialty materials circles. With the push for advancement in organic synthesis, this compound gives chemists a versatile option that makes exploration down new research paths not just possible, but often more efficient.

    What Makes This Compound Unique

    From my time working with heterocyclic compounds in the lab, I’ve seen how a single atom’s placement can open or limit the doors for synthetic pathways. This is especially true in the world of thiophene derivatives. Here, the bromine atom at position 4 and the methyl ester at position 3 aren’t just arbitrary features. They shape how this molecule reacts with others, making it a preferred building block where precision counts. The bromine acts as a functional handle for cross-coupling reactions like Suzuki and Stille, which are among the go-to options when constructing more complex molecules. I remember one project where the bromo-substituted intermediates outperformed their chloro or iodo counterparts by boosting yields and cutting back time wasted on purification.

    Details That Matter: Model and Purity

    Not every batch of 4-Bromothiophene-3-Carboxylic Acid Methyl Ester is equal. The most trustworthy sources deliver this product at high purity, typically above 98 percent, which keeps downstream processes cleaner and more predictable. I recall a synthesis where trace impurities from a lower-grade product compromised our catalyst’s activity, setting our work back by days. Consistent quality matters more than many realize until it’s gone.

    In my experience, the model most frequently used in research labs sticks to the methyl ester form, as it balances reactivity with manageable handling. Free acids can complicate storage, attracting moisture and reducing shelf life. The ester stays stable longer, which matters during long-term projects or when sharing reagents between teams in different locations.

    Key Uses That Drive Progress

    This methyl ester’s greatest strength lies in its flexibility within organic synthesis. Chemists use it for forging new bonds through a variety of cross-coupling methods. Its role in pharmaceutical research extends to constructing intermediates that eventually lead to bioactive molecules, experimental drugs, and diagnostic tools. In my experience, the electron-withdrawing effect of the ester group changes reactivity just enough to open pathways often blocked with the more electron-neutral thiophene systems.

    Agrochemical development teams follow similar logic. The search for effective pesticides or herbicides often hinges on tweaking molecular frameworks for selective toxicity and breakdown in the environment. Incorporating this methyl ester has helped teams design candidates that degrade more predictably or avoid certain side reactions.

    Materials scientists see value in this compound for its ability to fine-tune electronic properties in polymers and small-molecule devices. Modified thiophenes have found their way into OLED screens and solar cells, often because that bromine or ester allows for further functionalization late into synthesis. From my time collaborating with a team working on conductive polymers, we watched how the methyl ester group improved solubility and film-forming properties without sacrificing the charge-carrier mobility we needed.

    Comparing Apples to Apples: Differences from Other Products

    Anyone who’s spent time evaluating thiophene derivatives knows how seemingly minor substitutions can tip the scales between a project’s success and a stalled experiment. Let’s break down what sets this methyl ester apart from other commonly used analogs.

    Starting with 4-bromothiophene: on its own, this parent compound makes a decent coupling partner, but lacks the added vector for reactivity provided by the carboxylic acid ester. Introducing the ester group means chemists can perform additional functional group interconversions that aren’t possible with the base compound, such as saponification to yield the acid, or amidation for linking with larger biomolecules. During one collaboration, we realized that simply switching from the acid chloride to the methyl ester let us skip tedious protection-deprotection steps entirely.

    Contrast this with methyl 3-thiophenecarboxylate: lacking the bromine, there’s no point of attachment for transition-metal catalyzed couplings. While methyl 3-thiophenecarboxylate might be fine for some syntheses, anyone chasing new carbon-carbon bonds through palladium-catalyzed reactions will find themselves at a dead-end. Introducing bromine at the 4-position is a classic workaround and tends to give more consistent coupling yields than its 2- or 5-bromo isomers due to steric and electronic positioning.

    There's also a strong case for using this specific ester over free carboxylic acids. As anyone who’s stored or shipped both forms recognizes, the methyl ester holds up better during transit. This comes into play in multinational research or supply chains where conditions can swing between extremes. Fewer clumped samples and lower rates of hydrolysis translate to less waste and consistent results, especially on a tight grant schedule.

    Trust and Traceability

    No discussion about chemical intermediates is complete without touching on safety and sourcing. With increasing scrutiny over supply chain transparency, researchers demand reliable documentation about the origin, purity, and handling of every batch. Years spent in regulated lab environments taught me how even a single ambiguous certificate stirs up questions during audits or paper submissions.

    Labs and companies now turn to suppliers who provide verified analytical data—like NMR, HPLC, and elemental analysis—right up front. This isn’t just to meet regulatory hoops. Well-documented batches speed up troubleshooting and keep projects moving when surprises inevitably appear. The fact that leading suppliers typically retain reference samples for each lot means that, if something ever goes awry, tracing it back and learning from the misstep becomes much easier.

    Responsible Use and Safety Considerations

    4-Bromothiophene-3-Carboxylic Acid Methyl Ester, while immensely helpful for synthetic chemistry, prompts a discussion about safety in the lab. With a bromine atom in the structure, this compound demands careful storage and ventilation practices. From what I’ve observed, teams benefit when everyone respects the hazards and uses proper gloves, lab coats, and eye protection.

    Protocols for handling spills and disposing of waste are just as vital as reaction planning. In one academic lab, mismanaging a halogenated by-product led to regulatory headaches and a week of cleanup that no one enjoyed. Simple steps—labeling containers, having the right absorbent materials on hand, and keeping accurate inventory—make all the difference. Training new researchers in these habits from day one pays off in both safety and project continuity.

    Improving Access and Collaboration

    Accessing high-quality chemicals used to mean negotiating long wait times, unclear pricing, and the occasional surprise customs issue. These supply side stories used to slow research or push projects onto the back burner. The expansion of digital catalogs and improvements in communication make it much easier to source the right batch, at the purity required, with a paper trail that tracks from the manufacturer right to the bench.

    Some suppliers now offer tailored documentation packages that help teams in regulated industries—like pharmaceuticals or electronics—stay in compliance with evolving standards. I’ve seen how these improvements bring more confidence to group purchasing decisions and let lab managers focus on innovative work, not just paperwork.

    Opportunities For Green Chemistry

    As demands for environmentally responsible chemistry grow, researchers look for intermediates that combine effectiveness with minimized waste. 4-Bromothiophene-3-Carboxylic Acid Methyl Ester presents possibilities for more sustainable pathways. Some teams have reported that the selectivity afforded by the bromine and ester functional groups can reduce side reactions and improve atom efficiency during coupling and hydrolysis steps.

    There’s room for further progress. Manufacturers and end-users can work together to refine synthetic routes, exploring catalysts that generate less waste or allow for easier solvent recycling. In my own projects, scaling up reactions using this methyl ester prompted adjustments—switching from classic solvents to those with a better safety and environmental profile, for example. The flexibility of this compound gives it an edge as research teams strive to meet green chemistry benchmarks without compromising the science.

    Supporting Innovation in Drug Discovery

    The landscape of medicinal chemistry never stands still. Each year, teams race to build new molecular frameworks and chase the next effective therapeutic agent. Compounds like 4-Bromothiophene-3-Carboxylic Acid Methyl Ester support this quest, as their unique combination of functional groups can unlock bond-forming opportunities not accessible with simpler building blocks.

    I recall a phase of a project where we faced difficulty introducing new linkages between heteroaromatics and small peptide molecules. The methyl ester group served as both a protective group through the early steps and, later, a functional bridge allowing peptide coupling under mild conditions. Not all analogs performed with the same ease or efficiency. As researchers sift through hundreds of candidate intermediates, practical details like these influence what ends up actually used at the bench or in pilot plant settings.

    Boosting Efficiency in Synthetic Workflows

    High-throughput chemistry and automation keep gaining ground. These trends create pressure to standardize, automate, and scale synthesis while minimizing the risk of bottlenecks. 4-Bromothiophene-3-Carboxylic Acid Methyl Ester holds up well under these conditions due to its stability and predictable reactivity. Automated liquid handlers, often sensitive to viscosity and solubility variations, tend to perform more reliably with methyl esters than with free acids—fewer clogs mean more smooth cycles.

    From a project management view, this reliability shortens timelines and reduces the number of “fire drills”—the last-minute troubleshooting when a critical reagent fails to perform as expected. It’s not just about bench work, either. Analytical and process chemists benefit, since the product’s well-defined behavior helps NMR or chromatography teams quickly identify impurities or degradation products, making data reporting more straightforward.

    Challenges and Solutions: What Still Needs Fixing

    No chemical intermediate is perfect. Experienced chemists know that certain challenges can pop up when working with 4-Bromothiophene-3-Carboxylic Acid Methyl Ester—batch-to-batch consistency, moisture sensitivity, or variable cost depending on bromine pricing in global markets.

    Tackling these issues means forming closer partnerships with suppliers. Some of the most reliable sources now provide lot-specific analysis and a direct line for support, speeding up problem-solving before a discrepancy derails an entire synthesis. Sharing feedback—both good and bad—helps everyone along the chain adjust and improve. I remember times when quick access to a knowledgeable technical service rep meant salvaging weeks of work, whether the question related to solubility, purification, or residue handling.

    Long-term solutions might include investing in alternative, less hazardous bromination methods at the manufacturing level, as well as expanded documentation for new regulatory requirements. As synthetic chemistry shifts toward data-driven approaches, more robust databases on how functional group substitutions alter reactivity or stability could further cut down wasted effort and speed up discovery.

    Encouraging Education and Best Practices

    Everyone benefits from a workforce that really understands the tools at their disposal. Too often, the excitement to start a new synthesis overshadows the need for fundamental training—how to handle halogenated aromatics, how to avoid cross-contamination, why it matters to record subtle color changes or pH shifts. It only takes a few hours of practical instruction to prevent incidents and keep research on track.

    Companies and research institutions can reinforce best practices by making high-quality reference materials and method development guides broadly available. My mentors always stressed the value of “trust but verify”—never just accept a bottle at face value, but check every batch and document every use. These lessons stick with researchers through every step in their careers, supporting results that others can trust and repeat.

    The Takeaway: A Contributor to Next-Generation Science

    4-Bromothiophene-3-Carboxylic Acid Methyl Ester may look like another line on a lab inventory sheet, but to anyone pushing at the boundaries of modern chemistry or materials science, it’s more than that. Its unique combination of bromine and methyl ester functionality gives researchers a flexible, robust platform for innovation—whether that’s in new electronics for a greener future, next-generation medicines, or more sustainable materials.

    My direct experience and many conversations with colleagues tell me that success in science rarely hinges on the most glamorous ingredient. More often, it’s a well-chosen intermediate—stable, versatile, and properly documented—that makes a discovery possible and an outcome reproducible. This methyl ester stands out because it removes several hurdles along the way, giving researchers space to focus on what matters most: discovering, understanding, and building the next breakthrough.