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HS Code |
427336 |
| Chemical Name | 5-Bromo-2-Methyl-4(1H)-Pyrimidinone |
| Molecular Formula | C5H5BrN2O |
| Molecular Weight | 189.01 g/mol |
| Cas Number | 51504-25-7 |
| Appearance | White to off-white solid |
| Melting Point | 187-191 °C |
| Purity | Typically ≥98% |
| Solubility | Slightly soluble in water, soluble in DMSO and DMF |
| Storage Conditions | Store at 2-8°C, keep container tightly closed |
| Smiles | CC1=NC(=O)NC=C1Br |
| Inchi | InChI=1S/C5H5BrN2O/c1-3-7-4(6)2-8-5(3)9/h2H,1H3,(H,7,8,9) |
| Synonyms | 5-Bromo-2-methyluracil |
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The field of chemical synthesis hosts a roster of molecules few outside research labs ever hear about. Among these options, 5-Bromo-2-Methyl-4(1H)-Pyrimidinone builds real utility into a compact template. After spending years in labs and talking with researchers stuck on sluggish synthetic pathways, I know that a good heterocyclic intermediate can rewrite timelines for both small startups and big pharmaceutical teams. This pyrimidinone, with its subtle bromine substitution and methyl group, stands out not because it sits at the center of a flashy marketing campaign but because of how it quietly solves real problems for chemists grinding out new candidates day after day.
The structure of 5-Bromo-2-Methyl-4(1H)-Pyrimidinone tells much of its story. A bromine at position 5 and a methyl at position 2: on paper, these seem like tiny variations. In hands-on applications, these substitutions mean tangible differences in reactivity and compatibility with common cross-coupling, alkylation, and functionalization methods. I’ve watched bench chemists switch from generic pyrimidinones to this molecule during screening campaigns when tricky selectivity issues slow everything down. The bromine supports versatile derivatization without the uphill climb that comes from less-reactive halogens, while the methyl shifts both physical properties and substrate recognition profiles in downstream steps.
Lab professionals often complain about specification sheets that might as well be written in code. Real-world synthesis rarely cares as much about catalog numbers as about reliable purity, batch-to-batch consistency, and the simple predictability that lets you actually plan an experiment instead of gambling with unknowns. From conversation with process development folks at medium-sized pharma, I’ve learned the headaches caused by variable impurities or unpredictable melting points. In the best products, you’ll see clear white to off-white powder, melting somewhere in the 180-200°C window, and offering solubility that makes it manageable in both organic and some mildly aqueous conditions. Genuine value surfaces when those numbers translate to smoother filtration, shorter purification, and robust coupling steps down the line, rather than just checking off boxes on an online catalog.
I’ve run screens with half a dozen pyrimidinone derivatives, flipping between them in search of viable lead series. Most pyrimidinone core structures tend to blend together, but the switch to a bromine—without drifting into the pitfalls of trifluoromethyl or larger halogens—gives a sweet spot for functional group tolerance. Many colleagues chasing kinase inhibitors, anti-viral scaffolds, or agricultural chemistry prototypes lean on the 5-bromo variant. It manages to walk the line between sufficient reactivity for Suzuki or Buchwald-Hartwig coupling and not falling apart under basic or slightly acidic conditions. The bulkier halogens can introduce steric hindrance or drag down yields; fluorines might offer metabolic stability but lack the same flexibility in late-stage diversification.
Walk through an R&D unit working on small-molecule drugs, and you’ll spot pyrimidinones almost everywhere. The 5-Bromo-2-Methyl-4(1H)-Pyrimidinone offers a more streamlined approach for those who need to modify their molecules using Pd-catalyzed reactions or protect delicate functionalities during synthesis. In my own runs synthesizing analog libraries for SAR (Structure Activity Relationship) studies, swapping to this compound eased several bottlenecks. Its solubility in polar organic solvents can shave hours off work-up and minimize product loss, a small but important advantage during crunch periods. Medicinal chemists have flagged the bromine as a site for modular functionalization—offering a strategic anchor point without locking the rest of the molecule into unmanageable or overly-inert frameworks.
Every chemist eventually faces the monotonous task of tweaking substituents for days on end, driven by minor SAR trends or patent landscape concerns. At surface level, the methyl group at the 2-position doesn’t rewrite the rules, but it delivers subtle benefits in both solid-state properties and steric profile. Methyl at C2 slightly boosts lipophilicity without veering into territory where metabolic stability drastically suffers. In environmental persistence studies, such small tweaks often push a series into more sustainable territory, sidestepping the sort of late-stage failures regulatory teams fear. Bromine at C5 is a proven workhorse, opening doors for halogen dance reactions, selective metalation, or as a precursor for amination strategies relevant in developing APIs (Active Pharmaceutical Ingredients).
Having tested a range of halogenated and alkylated pyrimidinones, the temptation is always to chase after heavily functionalized, supposedly innovative scaffolds. In practice, added complexity rarely delivers proportional benefit. Chloro- or fluoro-derivatives may cost less, but they can restrict scaffold hopping or downstream derivatization due to their stubborn reaction profiles. I’ve observed more flexible workflow with the 5-bromo substitution, which leaves the door open to both further manipulation and a range of cross-coupling possibilities without demanding harsh or specialized conditions. I’ve heard from agrochemical synthesis veterans that bromo derivatives allow more rapid exploration of analogs without the time penalty of rigorous optimization after every step. For scale-up chemists, this can mean a difference of weeks—sometimes months—during the leap from gram to kilogram batches needed for pilot trials.
Back in one academic project tracking new anti-infective agents, I watched a postdoc struggle with solubility issues using unsubstituted pyrimidinones through several synthesis steps. The group later pivoted to 5-Bromo-2-Methyl-4(1H)-Pyrimidinone and reported an almost immediate drop in crystallization headaches and improved yields at scale. The patent literature also reflects this pivot; screening campaigns repeatedly turn toward bromo-pyrimidinones in hit-to-lead programs focused on enzyme inhibition. I’ve been part of a startup team trying to expand crop protection options, where a small adjustment—like the methyl group—sometimes makes all the difference in field trial stability or storage shelf-life. Having such a tool in the kit means less time down the rabbit hole of troubleshooting and more freedom to test useful molecular diversity before moving to expensive animal studies.
It’s common in bench-talk to downplay the importance of boring topics like batch consistency—until an unexpected impurity sets back weeks of work or triggers a regulatory inquiry. 5-Bromo-2-Methyl-4(1H)-Pyrimidinone, when sourced from suppliers who maintain tight quality controls, brings crucial peace of mind. Labs relying on consistent melting range and absence of common contaminants reduce revalidation fatigue and project interruption. From speaking to QA experts in pharmaceutical outsourcing, I know the extra investment in solid sourcing pays off, especially with a compound whose utility depends on how reproducibly it plugs into longer multistep syntheses. The alternative is running the risk of introducing variable side-products, spiking batch failures, or scrambling to explain failed reactions during audits.
The world of core lab chemicals always features a cost-benefit negotiation. While the bromo-methyl pyrimidinone isn’t the cheapest catalog item in its family, it occupies an important middle ground—available at larger scales when needed, but refined enough to avoid the common headaches of discount chemical sources. Cost-conscious buyers could pick simpler analogs, yet I’ve seen time after time how a few extra dollars up front can save significantly on downstream purification or reruns. Even in academic labs tied to rigid budgets, principal investigators are slowly moving away from false savings on sketchy intermediates and betting on declines in attrition rate when deployable, high-quality material enters the mix.
Sustainability gets talked about endlessly across the modern chemical industry. The truth is, the bulk of environmental footprint for medicinal and agrochemical R&D stems from failures, wasted material, and inefficient work-up steps. With its reliable reactivity and manageable side-product profile, 5-Bromo-2-Methyl-4(1H)-Pyrimidinone helps teams carry more reactions through to completion without ballooning the solvent or reagent consumption. In my own experience, less downtime handling stubborn by-products and less failed purification means less total chemical waste. Safety-wise, the compound doesn’t carry the acute handling risks of strongly basic, pyrophoric, or air-sensitive intermediates—another side benefit appreciated by safety officers seeking to keep accident rates in check during routine operations.
Debates about the best intermediates fill conference panels every year. There’s no perfect answer, but the steady preference for the 5-bromo, 2-methyl handle in the pyrimidinone series demonstrates genuine field-tested dependability. The real value often shows up in speed: teams can evaluate more molecular diversity in less time, screen for unexpected off-target activities earlier, and compress project timelines in crunch periods. Busy chemists appreciate skipping the scavenger hunt through the freezer for shelf-stable intermediates capable of supporting a dozen pathways. The difference a single smart intermediate can make ripples out, impacting candidate selection, partnership discussions, and, most importantly, bench scientists slogging through the nitty-gritty of real-world synthesis. Personally, the compound has saved me entire days otherwise wasted debugging clogging columns or troubleshooting non-intuitive side pathways.
Bridging the gap between milligram-scale screening and multi-kilo campaign runs, few intermediates remain as approachable as 5-Bromo-2-Methyl-4(1H)-Pyrimidinone. As operations ramp up, factors like powder flow, formation of dust, or stability in bulk storage start to matter more than a perfect analytical purity at the bench level. This compound, with its stable solid-state character and amenable handling properties, supports both early and late-stage development. On more than one occasion, I’ve heard from scale-up technicians thankful for intermediates that resist caking or degradation during months-long warehouse storage, ensuring reliable downstream supply without expensive mitigation measures.
Many pharma and biotech professionals consider intellectual property strategies even during early hit development. By choosing a versatile intermediate like 5-Bromo-2-Methyl-4(1H)-Pyrimidinone, teams can establish a base for protected synthetic routes without crowding into already-dense patent landscapes. My discussions with strategy consultants point out that covering a new series anchored at the 5-bromo position opens up claims on novel analogs while giving synthetic teams room to maneuver as new SAR insights come in. This flexibility shields programs from some abrupt shifts in research direction forced by late-emerging patent blockades—an underappreciated advantage in competitive therapeutic areas.
Chemical synthesis has always mixed tradition, discovery, and relentless optimization. Looking at emerging trends—a push for sustainable manufacturing, pressure to bring candidates to clinic faster, and the need for affordable development cycles—tools like 5-Bromo-2-Methyl-4(1H)-Pyrimidinone have become even more important. In the last few years, interdisciplinary teams have drawn on its robustness and flexibility to streamline complex syntheses that in previous eras would have stalled at the design table. While synthetic chemistry never stands still, and new building blocks constantly try for the spotlight, a compound that consistently delivers a balance of reactivity, stability, and adaptability earns its place in the toolkit.
No single molecule solves the puzzle for every workflow. Yet, chemists learn to lean on intermediates that reduce risk and expedite progress. In my direct experience, turning to 5-Bromo-2-Methyl-4(1H)-Pyrimidinone speeds up the cycle from idea to workable prototype by trimming complexity from core steps. Challenges in contamination, downstream yield, and unpredictable reactivity demand more than off-the-shelf answers—a proven intermediate offers a measure of reliability that helps teams regroup and move forward. Connecting with colleagues across the industry, I see growing awareness around identifying such compounds early and building workflow flexibility around their strengths. Rather than fighting uphill with raw reagents offering little margin for error, teams can invest their time and attention in the places that matter: novel molecular design, impactful biological screening, and efficient scaling, building off the sturdy foundation this compound provides.
My years at the bench taught me to appreciate the understated value of well-chosen intermediates. Choosing 5-Bromo-2-Methyl-4(1H)-Pyrimidinone isn’t just about ticking a box—it’s about stacking the odds in favor of progress by minimizing common obstacles. Its approachable reactivity and manageable physical form reduce time lost to troubleshooting, material waste, and dead ends that can sap team momentum. Each research group has unique pain points, but those working with tightly regulated timelines or budgets will recognize the advantage of a compound that bends without breaking under the push and pull of ambitious synthesis. The next time project managers or lead chemists debate which intermediates to stock and scale, experience argues for those that not only perform in initial tests but also streamline the whole development chain, precisely as this compound does.
Pyrimidinones will never grace the covers of glossy magazines, but in the trenches of chemical research, their importance speaks through the efficiency, reliability, and flexibility they bring. For teams focused on progress, not perfection, 5-Bromo-2-Methyl-4(1H)-Pyrimidinone has emerged as a backbone compound. Its functional group arrangement, dependable sourcing, and accessible handling characteristics carve out a valuable space between novelty and utility. Whether the goal is to build a fresh antiviral pipeline, take a shot at the next big agrochemical breakthrough, or simply get through a battery of SAR iterations with less wasted effort, this pyrimidinone supports chemists every step of the way. Trust built through use counts for more than any marketing claim, and the product’s track record among lab professionals points to a simple conclusion: some molecules, by virtue of design and dependability, earn a place in every research chemist’s wheelhouse.