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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.