|
HS Code |
298213 |
| Chemical Name | 3,5-Dibromo-2-Methylthiophene |
| Molecular Formula | C5H4Br2S |
| Molecular Weight | 271.96 |
| Appearance | Pale yellow to light brown solid |
| Cas Number | 134441-08-0 |
| Smiles | CC1=CC(=CS1Br)Br |
| Melting Point | 48-52°C |
| Density | 2.07 g/cm3 (approximate, 20°C) |
| Purity | Typically ≥ 97% |
| Solubility | Soluble in organic solvents (e.g., DCM, chloroform) |
| Synonyms | 2-Methyl-3,5-dibromothiophene |
| Storage Temperature | Store at 2-8°C |
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Specialty chemicals have a way of quietly shaping the modern world, and every so often, a molecule comes along that brings a real edge to cutting-edge research and production. Take 3,5-Dibromo-2-Methylthiophene, for example—a compound that’s found its way into labs and workshops focused on innovation. Chemists who spend long hours looking for dependable aromatic building blocks won’t have a hard time spotting the practical value that 3,5-Dibromo-2-Methylthiophene brings to the workbench.
At first sight, this is a clear to pale yellow liquid, sometimes appearing as a solid at lower temperatures. Packaged in bottles that protect it from moisture, this compound features a thiophene ring substituted with two bromine atoms at positions 3 and 5 and a methyl group at position 2. The arrangement might sound esoteric, but for anyone involved in organic synthesis, this is a winning combination. It offers both reactivity and stability, which is rare in molecules that pack such functional groups so closely together.
Researchers count on thiophene derivatives because sulfur rings make excellent backbones for more complex molecules—especially in pharmaceuticals, specialty polymers, and certain types of agricultural chemistry. This specific model, featuring two bromine atoms and a methyl group, stands out from the crowd due to its unique substitution pattern. Those bromine atoms open the door to a variety of coupling reactions—Suzuki, Stille, Heck, you name it—while the methyl group fine-tunes both electronic and steric properties. That gives chemists more ability to tweak a target molecule’s behavior down the track.
From my own time in academic labs, I’ve seen how single reagents can define the success or failure of a route. One bottleneck in synthesizing heteroaromatic compounds is often the initial selection of the halogenated starting material. Conventional thiophenes, such as 2-bromothiophene or unsubstituted thiophene, often lack the selectivity or offer less control in subsequent steps. This is where the 3,5-dibromo-2-methyl version stands apart. It gives researchers a head start on selectivity and functional group compatibility, making life easier for those looking to engineer more sophisticated molecules, without wasting time on tedious protection and deprotection sequences.
Makers of advanced materials use this product because it can serve as a pivot in oligomer or polymer synthesis. For those working on organic electronics—think OLEDs or certain solar cell materials—precision in the substitution pattern means more predictable results. In the pharmaceutical sector, the molecule’s unique substitution allows medicinal chemists to explore new territory in drug design, since bromine atoms can be swapped for more complex side chains with relative ease through cross-coupling reactions. The endgame is usually greater biological activity or better pharmacokinetics—goals that are often hard to hit with other scaffolds.
It might be tempting to put all thiophenes into one basket. The reality diverges quickly for anyone who has ever tried to move from lab scale to pilot or production scale. Lots of industries view 3,5-dibromo-2-methylthiophene as a gold standard because of its consistent behavior in multi-step processes. Even in physically demanding conditions—high heat, strong bases, or metal-catalyzed environments—the thiophene ring remains intact, and the clean reactivity of the bromines keeps the process running smoothly. Other related compounds can sometimes form nasty by-products or slow the reaction down, requiring extra purification and hiking up costs.
Specialists in synthetic chemistry have seen shifts in their approach as new reagents demonstrate their worth. Twenty years ago, a typical project would rely heavily on monosubstituted bromothiophenes, but these lack the same flexibility afforded by the 3,5-substitution. Adding a methyl group doesn’t just change the electronics—it can also impact solubility, physical handling, and downstream reactivity. For instance, in certain palladium-catalyzed couplings, this substitution prevents unwanted by-products and limits overreaction, which saves both material and time. There’s less risk of your project derailing because of an off-pathway reaction.
Sustainability is more than a buzzword. In many facilities, selecting the right starting materials directly impacts not just the efficiency of a project, but also its footprint. Using a reliable, clean-reacting compound helps reduce waste, minimize solvent use, and avoid tricky purification steps. That puts less pressure on researchers, technicians, and the environment. I’ve worked on projects where swapping in 3,5-dibromo-2-methylthiophene turned a multi-day, solvent-heavy sequence into a cleaner, faster operation. The difference boils down to fewer chromatography cartridges, easier lot tracing, and smoother compliance with green chemistry metrics.
Some competing halothiophene derivatives show patchy reactivity or introduce side reactions that complicate things in the middle or late stages of synthesis. These hiccups not only annoy the folks on the bench, but they can also ramp up costs and delay the path from idea to actual product. 3,5-dibromo-2-methylthiophene, on the other hand, offers consistent yields in common metal-catalyzed couplings and stands up to a variety of demanding reagents without breaking stride. Its design keeps the process simple, helping small labs and larger production units alike stay focused on the end goal instead of fixing problems halfway through.
Through direct experience and a steady stream of feedback from those working in pharma, specialty materials, and research labs, it’s become clear that certain reagents do more than just fill a spot on a shelf. They become central to how projects progress. This molecule stays competitive not by being the loudest or most exotic, but by showing its worth where it matters. Chemists constantly compare yields, ease of handling, and process robustness among halogenated thiophenes. Here, the 3,5-disubstitution pattern gives better odds at making targeted C–C bonds, whether you’re building up an electron-rich molecule for a drug discovery campaign or laying out building blocks for next-generation polymers.
In practice, the model number or CAS isn’t just a reference for ordering; it serves as shorthand for a set of physical and chemical promises. Its boiling point and solubility in standard organic solvents make it approachable for a range of reaction setups. Those who handle scale-ups often face logistical nightmares when by-products build up or when reaction cords break down unpredictably. 3,5-Dibromo-2-Methylthiophene offers a welcome level of predictability, lowering the stakes of each new batch and smoothing over the path to larger quantities—traits seasoned chemists learn to value over flashier but trickier alternatives.
Working in both academic and industrial labs has shown me that the best materials don’t just impress with purity or shelf life—they play nicely across equipment and teams. Early-stage medicinal chemists need clean, high-yielding transformations, while process chemists on the back end demand scalability and rugged performance. Bridging that divide cuts both headaches and hours from development. I remember fielding calls from both sides of the process line: one team thrilled that a key intermediate came together without a hitch, another team pleased that there wasn’t any gunk fouling up the reactors. When all eyes are on cost and time, cutting out problem reagents becomes a necessity, not a luxury.
Students, postdocs, and senior scientists alike influence the popularity of a reagent. I’ve lost count of the times people favor feedstocks that ‘just work’ over those that force you to fine-tune every parameter for each batch. For more niche applications, having two bromine atoms positioned at 3 and 5 on the thiophene ring—rather than just one or a mispositioned pair—provides key entry points for building complexity. Many frontline researchers find themselves swapping stories about which reagents stand up to real-world stress; 3,5-dibromo-2-methylthiophene lands on the shortlist every time the conversation turns to reliability and convenience.
Data from published organic synthesis studies show strong uptake of dibromo-thiophenes in large combinatorial libraries, particularly for generating small-molecule inhibitors and high-performance materials. The methyl group at the 2-position of this model boosts selectivity in certain Pd- or Ni-catalyzed couplings, reducing unwanted dialkylated or oligomeric by-products. That boosts atom economy, lowers risk, and improves process safety—a triple win for operations required to meet international regulatory and environmental standards.
In the context of specialty plastics, especially those involved in flexible electronics and sensors, small changes in starting material purity can have outsize effects on device performance. Weak links in the chain sometimes originate from impurities in building block chemicals, causing expensive hiccups further along. Technicians who lean on 3,5-dibromo-2-methylthiophene have reported strong, repeatable results across different batches and scales. That sort of track record speaks to solid manufacturing control and thoughtful quality assurance on the supplier side.
Research into sustainable and efficient synthetic pathways—funded by both public and private bodies—often points to halogenated thiophenes as key enablers. Reagents that work cleanly in aqueous or mixed-phase chemistry, resist base- or acid-driven decomposition, and show regularity in purification, all help decrease the burden of downstream waste treatment. With mounting attention on environmental and workplace safety benchmarks, chemical producers now aim to source reagents that won’t punch above their environmental weight.
Looking across the shelf of thiophene derivatives, you’ll find a collection of isomers and analogues: 2-bromothiophene, 3-bromothiophene, 2,5-dibromothiophene, and methyl-substituted relatives. Simple monobrominated compounds provide entry to some cross-coupling protocols but fall short when dual functionalization matters. Compounds like 2,5-dibromothiophene lack the methyl substitution, leading to differences in solubility, volatility, and reactivity profiles. For those who care about final product attributes—crystallinity in polymers, pharmacophore docking in drug molecules, or even the color and photophysical changes in OLED materials—these small details become strategic levers.
The inclusion of a methyl group alongside the double bromination enables less-crowded reactions when complexing with metal catalysts. That means fewer false starts, less tinkering with solvents, and less fiddling with temperature and pressure settings. Practicing chemists soon realize they can’t swap out 3,5-dibromo-2-methylthiophene for simpler models without risking changes in product profile or yield. In large-scale or compliance-driven facilities, these “minor” differences carry real regulatory implications, since process repeatability and impurity profiles face close scrutiny from auditors and health authorities.
I’ve known projects to stall by taking the cheaper, less-specialized route, only for teams to double back and return to the more sophisticated starting material. Narrowing the field to the best reagent for the intended purpose isn’t just about convenience—it builds confidence in the whole chain from bench to market, lowers recall rates, and lets teams keep their focus on innovation instead of last-minute troubleshooting.
No honest commentary would skip practical realities. The brominated and methylated thiophene is best stored in tightly sealed glass bottles away from heat and light sources. Anyone who has worked in synthetic labs knows that unexpected volatility or decomposition can set a project back. While this thiophene stands up to regular bench handling, appropriate personal protective equipment always makes sense—gloves, goggles, and fume hood protocols. Its relatively low volatility compared to smaller thiophenes offers a safer working environment, especially during scale-up. Waste streams from reactions with this compound typically include bromide salts and organic by-products, which are manageable by standard chemical disposal protocols.
Many suppliers include purity checks such as NMR and GC-MS readings, which are a boon for quality control. Those working in regulated environments appreciate any documentation supporting traceability and consistent behavior. Any minor investment in quality reagents can pay back exponentially on the time and cost side.
Every chemical has limits, and 3,5-dibromo-2-methylthiophene is no exception. Supply chain resilience, price spikes in brominated feedstocks, and transport restrictions related to hazardous materials remain challenges for some regions and smaller buyers. Addressing these issues calls for broader industry coordination, investment in greener routes to bromothiophenes, and improvements in regional supplier networks. Initiatives that support domestic production capacity and less hazardous brominating technologies could insulate users from shocks and help decouple costs from global supply volatility. While recycling and recovery of bromine sources are gaining ground, further research and implementation could help make the supply of these specialty chemicals both cleaner and more stable.
There is always room for improvement in packaging, batch tracking, and end-of-life management. Packaging built for safety and environmental compliance already prevents most spill and contamination risks, but streamlined transportation for small-volume R&D operations would smooth access to this valuable reagent. More suppliers publishing full analytical dossiers and supporting documentation would give users more confidence and could accelerate regulatory acceptance in sensitive applications.
Small molecules like 3,5-dibromo-2-methylthiophene might not make headlines, but their impact continues to grow as new technology fields demand ever more reliable, tailored building blocks. Whether in the next blockbuster drug, a new kind of flexible display, or specialized agrochemical products, this benzothiophene derivative quietly raises the quality and reliability of research and manufacturing. Choosing the right starting material can be the difference between a breakthrough and a dead end. That’s something both bench chemists and industry leaders come to appreciate after years in the field. As markets demand smarter, safer, and greener solutions, dependable reagents like this one will continue to hold their ground as essentials in both established and emerging sectors.