|
HS Code |
991899 |
| Chemical Name | 5-Amino-2-Bromopyrimidine |
| Cas Number | 4727-72-4 |
| Molecular Formula | C4H4BrN3 |
| Molecular Weight | 173.00 g/mol |
| Appearance | White to light yellow solid |
| Melting Point | 120-124°C |
| Purity | Typically ≥98% |
| Solubility | Soluble in DMSO and methanol |
| Storage Conditions | Store at room temperature, in a tightly sealed container |
| Smiles | C1=CN=C(N=C1Br)N |
| Inchi | InChI=1S/C4H4BrN3/c5-3-1-8-4(6)7-2-3/h1-2H,(H2,6,7,8) |
| Synonyms | 2-Bromo-5-aminopyrimidine |
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Scientific discovery rarely moves in a straight, predictable line. Sometimes, one small molecule can change the way a lab approaches a full line of research. 5-Amino-2-Bromopyrimidine turns up as one of those unsung building blocks in organic synthesis and medicinal chemistry. For chemists who spend their late nights hunched over benches, scanning TLC plates, and chasing the subtleties of challenging reactions, this compound stands as a reliable friend. Its unique structure, a pyrimidine ring carrying both amino and bromo functional groups, gives it versatility that stretches well beyond a one-use wonder. Whether you are chasing that stubborn heterocyclic target or optimizing a pathway to a novel drug lead, it’s worth learning some hard facts about what sets this molecule apart from other options in the catalog.
With a molecular formula of C4H4BrN3, 5-Amino-2-Bromopyrimidine seems modest at first glance. Yet its fusion of functional diversity is the very thing giving synthetic chemists a handful of new routes. The amino group at position five opens wide the door for coupling reactions, as every biochemist or pharmaceutical researcher knows. The bromine at position two equips it for cross-coupling—Suzuki, Stille, Heck—making it a gateway to richer motifs or more complex heterocycles. This dual functionalization reduces both time and cost for teams aiming to expand chemical libraries or speed up lead optimization in early-stage drug research. No other similar pyrimidine in a basic toolkit offers matching reactivity with such selective precision.
In my years wandering through the maze of synthetic projects, I’ve seen time and again how a well-placed building block transforms a tough step into a routine part of the workflow. Take nucleophilic aromatic substitution. With 5-Amino-2-Bromopyrimidine, options multiply, as the bromine's electron-withdrawing behavior makes the ring more susceptible to attack, and the amino group can stabilize intermediates or act as a springboard for protection, activation or further functionalization. That’s a major stride for any medicinal chemistry group balancing between innovation and keeping a sane cost structure.
Medicinal chemistry has shifted from brute-force approaches to more thoughtful design, especially as biological targets increase in complexity. Modern pharmaceutical research demands building blocks that do more than just fill a space on the shelf. 5-Amino-2-Bromopyrimidine fits right into that philosophy. Heterocyclic chemistry relies on precise, reliable starting materials for developing kinase inhibitors, anti-infectives, and anti-cancer agents. You’ll see pyrimidine cores in drugs like cytarabine, lamivudine, and various experimental kinase inhibitors.
Generating diverse analogs from a single scaffold allows researchers to scan SAR (structure-activity relationship) with a smaller set of resources, saving not just money but precious weeks or months. This molecule acts as an ideal pivot point—switching a substituent on the amino group or modifying the bromo-link can yield families of compounds with new potency or selectivity. Imagine tackling kinase selectivity with a more agile scaffold or unlocking new anti-fungal agents by shifting just one carbon round the ring. Flexibility like this keeps a research pipeline humming. Conversely, using an alternative such as 2,4-dibromopyrimidine limits customizability and adds steps; 5-Amino-2-Bromopyrimidine gives a deliberate, manageable handle on both positions without requiring starting from scratch.
Looking at recent literature, you’ll notice a steady march of patent filings and research papers featuring novel pyrimidine derivatives hinging on exactly this type of molecule. Leading pharmaceutical labs prioritize synthetic efficiency, and the amino/bromo pairing lets teams shuffle between strategies—amide bond formations, arylations, alkylations—with fewer purification headaches and no need for esoteric conditions. No more running reactions at liquid ammonia temperatures for a day and praying for clean conversion. Ease of derivatization counts in the real world of R&D, not just in the classroom or on retrosynthesis paper exercises.
The catalog of pyrimidine derivatives isn’t small. Even so, 5-Amino-2-Bromopyrimidine drills into a specific need. Consider other options—plain 2-bromopyrimidine or mixtures with bulkier alkyl or alkoxy groups. These alternatives often mean you sacrifice some flexibility at the amino position in exchange for different reactivity patterns. Many lack the straightforward N-H that lets researchers easily tack on new functionalities. When timeline pressure gets tight, the difference between direct transformation and three extra protecting-group steps can make or break a whole project’s momentum.
In process chemistry, the molecule's physical properties—crystalline solid, manageable melting point, moderate solubility in polar and nonpolar solvents—ease purification and handling concerns. An added bonus for those prepping larger scale reactions is that it doesn’t throw up the toxicological or explosive red flags you’d find with some alternative halogenated heterocycles. In my own troubleshooting, I’ve found fewer headaches when pushing the scales above a few grams. It makes a practical difference, especially in pilot scale or even small commercial batch work.
Take, for example, 2-amino-4,6-dichloropyrimidine, a close cousin often considered as a synthetic intermediate. It bumps up the potential for multiple reaction sites, which can mean a tangle of regioisomers and tough separations—the bane of every purification step. The 5-Amino-2-Bromopyrimidine structure streamlines pathways to single, defined products, cutting down on both wasted reagents and labor costs. Anyone who has worked late into the night purifying a messy column knows the value of a more predictable, controllable starting point.
Small pharmaceutical outfits and academic teams alike use this model as a starting line for complicated synthetic programs. For example, in kinase inhibitor development, chemical space exploration often hinges on introducing precise substituents to the six-membered ring, then testing activity against a panel of protein targets. The amino group at position five, unlike bulkier alkyl replacements, delivers a touchpoint for hydrogen bonding in the active site of enzymes—a vital consideration in structure-based drug design.
Outside of medicinal chemistry, materials science has started exploring these heterocyclic units as building blocks for new polymers and high-performance dyes. Organic electronics—OLEDs, for example—often benefit from heterocycles with robust electronic features like those found in 5-Amino-2-Bromopyrimidine. The electron-rich amino group and the halogen’s modulating effect on aromaticity combine to deliver properties not achievable through simple benzene analogs.
Beyond specialized applications, educational settings draw on classic reactions with this molecule to teach cross-coupling, amination and substitution chemistry. Undergraduate organic teaching labs occasionally use it to show students the differences in reactivity between halogen and amino substituents, providing hands-on experience with real-world reagents. As a former teaching assistant, I watched young chemists work out the subtleties of selectivity and learn that smart building block choice could save both time and solvents.
Not every supplier sustains the highest standards in chemical purity. In my experience, small amounts of residual starting materials, contamination with similar pyrimidines, or the presence of unwanted by-products can plague downstream applications. Solid NMR, HPLC, and melting point data back up the best offerings. Labs working on fine-tuned synthetic schemes rely on consistent, repeatable batches for confidence that results will scale from micrograms to multigram efforts. Reproducibility, core to good scientific practice, stands or falls on source reliability.
A chemist’s confidence in a reagent rarely comes from bold marketing. We trust data, reputation, and hard-won feedback from peers. Bulk batches with full documentation, coupled with accessible spectral and physical data, carry more weight than low-cost listings with spotty records. For production workflows, the difference between a 97% and a 99% pure batch can spill into performance metrics, stability testing and IP protection. For students, reliable samples mean an easier learning curve—and fewer frustrated nights repeating a stalled transformation.
Long gone are the days when safety profiles sat as a distant afterthought. Teams now look for not only regulatory alignment but real improvements to staff well-being. 5-Amino-2-Bromopyrimidine’s track record places it on solid ground for general laboratory work. Proper handling, PPE, and ventilation still apply, of course, as with any moderately active halogenated compound. For scale-up or routine use, the lower vapor pressure and solid state cut inhalation risk and make spills easier to manage.
Environmental stewardship doesn’t have to clash with research speed. Synthetic processes with this building block consume less solvent and run at milder temperatures than many of their chlorinated cousins. Efficiency gains place smaller burdens on energy use and waste disposal. With standards tightening in academic, commercial, and government research programs, small choices add up; a better-behaved reagent streamlines compliance and reduces secondary risk. Institutional review boards and grant bodies now weigh environmental impact—smart selection at the start boosts a program’s reputation for responsibility.
Every research group, whether in academia or industry, feels the pressure to publish, patent, and move projects faster without blowing the budget. 5-Amino-2-Bromopyrimidine keeps finding traction because of its real-world reliability, breadth of applicability, and savings in time, materials, and process engineering. The hard truth from the lab benches is that versatile, dependable building blocks earn their place not from hype but from hard, reproducible results.
Peer-reviewed studies highlight both raw data and anecdotal commentary on why certain scaffolds persist in the literature. Teams that share their troubleshooting and best practices tend to circle back to compounds that cut out extra steps, reduce risks of side reactions, and don’t create headaches at scale-up. As research funding grows more competitive, efficiency and reproducibility make or break a program’s long-term prospects—not just a matter of keeping on budget but ensuring that projects withstand the scrutiny of regulatory review or investor due diligence.
No one molecule will solve every problem. Still, 5-Amino-2-Bromopyrimidine acts as a case study in how targeted, thoughtfully designed intermediates can streamline everything from first-stage screening to late-stage development. Our collective experience in synthetic chemistry suggests that the building blocks we return to again and again are those that handle a wide range of transformations, mesh with the newest catalytic techniques, and play nice with both established and ground-breaking methodologies.
I’ve watched colleagues in bioorthogonal chemistry riff on new applications, adapting pyrimidine cores to bioconjugation and fluorescent labeling. As diagnostics and therapeutics blur, the same nucleotide-like structures find homes in imaging agents and emerging platforms for targeted drug delivery. The adaptability 5-Amino-2-Bromopyrimidine brings, both for substitutions and downstream applications, matches perfectly with the rapid pace of discovery we now see in both university settings and the pharmaceutical sector.
Even graduate students, tasked with exploring some tricky new pathway, benefit from a reliable backbone. Choosing a starting material that works well in classic substitution but can also handle new ligation chemistry means more experiments reach publication. The career impact of fewer failed runs and cleaner data accumulates quickly, regardless of whether you’re targeting nature-inspired syntheses, new materials, or platform technologies for diagnostics.
Cost still rules much of the decision-making, particularly for academic or startup groups working on a shoestring. 5-Amino-2-Bromopyrimidine lands in a sweet spot. It’s neither so exotic that sourcing takes weeks nor so cheap as to be suspect in quality. Reliable distributors keep stocks on hand, provide documentation, and maintain competitive per-gram pricing for orders from small vials up to kilogram drums. Labs benefit from flexibility—order for a single project, or scale up without renegotiating contracts or facing sticker shock.
Responsive customer support, transparent documentation, and community feedback all factor into sourcing decisions as much as simple catalog pricing. My own lab learned not to chase the lowest bid; reliability, certification (ISO, GMP where needed), and documented lot-to-lot consistency saved hours, and confidence in regulatory compliance matters for later development.
Collaboration between synthetic chemists, biologists, and engineers now defines the research culture. Building blocks like this expand the reach for interdisciplinary teams, bridging chemistry with biology, medicine, and physics. Computational chemists modeling enzyme binding find the regular, predictable shape of this scaffold an asset; medicinal chemists value the reactivity and derivatization potential; materials scientists see pathways to novel functional polymers.
Working through a multi-year drug design collaboration, we combined parallel synthesis with fast turnover assays. The adaptability of 5-Amino-2-Bromopyrimidine allowed us to generate meaningful SAR data quickly, feeding structural hypotheses back into the chemistry pipeline. The same project shifted gears into the diagnostic space, leveraging the molecule’s compatibility with labeling and surface chemistry for sensor development. Flexibility, responsiveness, and reliable handling opened possibilities that would have shut out more rigid intermediates with single-purpose applications.
Decades of experience and thousands of research papers show that the origins of great chemistry lie in the first choices made at the planning table. Picking 5-Amino-2-Bromopyrimidine as a core reagent signals a willingness to invest in flexible, reliable methods. The continual refinement of analytical, preparative, and purification techniques underscores that the benefits of such smart intermediates accumulate for both discovery and process chemistry.
Regulatory landscapes shift and new, greener pathways keep arriving. Making competent choices about building blocks, reagents, and synthetic steps influences outcomes well past the project at hand. Institutions putting sustainability, reproducibility, and technological agility at the center of their strategy often turn to reliable multi-functional compounds. From early screening libraries to advanced material synthesis, the capacity to pivot—to adapt molecule, process, and technology—defines the modern research environment.
In all of this, 5-Amino-2-Bromopyrimidine shows why a single molecule can continue to shape scientific progress. My own lab’s experiences, alongside feedback from across academia and industry, confirm: reliability, broad applicability, and trusted documentation matter at every stage. A flexible, well understood starting material saves more than just money and labor. It lays the foundation for discovery, learning, and ongoing progress in a field where both challenges and opportunities grow with each passing year.