|
HS Code |
754094 |
| Iupac Name | 4-Bromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one |
| Molecular Formula | C7H4BrN3O |
| Molecular Weight | 226.03 |
| Cas Number | 942122-31-8 |
| Appearance | Off-white to light brown solid |
| Melting Point | 220-224°C |
| Purity | Typically ≥97% |
| Solubility | Slightly soluble in DMSO and DMF |
| Smiles | C1=C(NC2=NC=CC(=O)C2=C1)Br |
| Inchi | InChI=1S/C7H4BrN3O/c8-4-1-2-9-7-5(4)3-6(12)11-10-7/h1-3H,(H,11,12) |
| Storage Temperature | 2-8°C |
| Synonyms | 4-Bromo-2-oxo-1,2-dihydro-1H-pyrrolo[2,3-b]pyridine |
As an accredited 4-Bromo-1H-Pyrrolo[2,3-B]Pyridine-2(3H)-One factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
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These days, research professionals experience an ever-widening array of chemical compounds, each vying for attention in the vast world of small-molecule innovation. After years working in the medicinal chemistry field, I’ve seen the shift — not every molecule earns a spot on the bench, but 4-Bromo-1H-Pyrrolo[2,3-b]pyridine-2(3H)-one has managed to stand out for a few specific reasons. In an ocean of N-heterocycles, it’s not always about being rare; sometimes, it’s about being right for the job.
For those who haven’t held a sample of 4-Bromo-1H-Pyrrolo[2,3-b]pyridine-2(3H)-one in the palm of their hand, the structure can seem complex at first glance. We see the fused pyrrolo-pyridine core — a motif that features in many biologically interesting scaffolds. The bromine atom at the 4-position brings a reactive handle, letting synthetic chemists move into multiple directions. Alongside the carbonyl at the 2-position, this small change opens the door for easy substitution and robust functionalization.
Anyone who has ever faced a tricky amination or a Pd-catalyzed cross-coupling will quickly appreciate how the bromo group serves as a launching pad for further modifications. I recall several projects where lesser-known analogs of this scaffold unlocked access to kinase inhibitors and CNS agents — not by mimicking classics, but by venturing just far enough off the beaten path to inspire patentable, potent new leads.
Chemists need reliable building blocks that withstand solvent and temperature swings. In my experience, the stability of this compound under typical laboratory conditions matches the high bar set by more common starting materials. Its crystalline form — observed in many commercially available batches — allows for accurate weighing and reproducibility, which matters greatly when scaling from milligram screens to gram-level synthesis.
For fields as demanding as pharmaceutical and agrochemical discovery, this isn’t just about doing a job. Each research cycle runs against the clock and tight budgets, so a starting material that consistently delivers, without the usual headaches of purification or decomposition, earns its way onto repeat orders. Over the years, my colleagues gravitated toward this molecule not because brochure descriptions promised miracles, but because the track record spoke for itself during library syntheses and impurity challenge runs.
Drug designers and material scientists both look for heterocycles that offer a combination of rigidity and reactivity. In protease and kinase inhibitor campaigns, that pyrrolo[2,3-b]pyridine core serves as solid pharmacophore territory. Unlike simple indoles, the presence of the nitrogen atom in the fused ring enables unique hydrogen-bonding patterns — sometimes critical in shifting a compound from moderate to strong binding in SAR work. I remember more than one case where swapping out a plain indole with a 4-bromo-pyrrolo[2,3-b]pyridinone analog turned around an otherwise stagnant project.
There’s also a resurgence of interest in this class of compounds for material chemistry, with teams exploring how the planar aromatic system supports charge transfer and fluorescence. Having handled hundreds of heteroaromatics, I find that both benchwork and computational modeling go smoother when the building blocks feature predictable electronics and reactivity patterns, two qualities this compound regularly demonstrates.
Comparing 4-Bromo-1H-Pyrrolo[2,3-b]pyridine-2(3H)-one to others in its class, there’s more than just a structural tweak at play. While many researchers lump N-heterocycles together, nuanced differences shape the ultimate fate of a project. This molecule’s fusion of electron-rich and electron-deficient centers allows for functional group transformations not always possible with less polarized heterocycles. It also opens up late-stage diversification, an essential feature during lead optimization when small molecular changes matter.
Reflecting on personal lab experience, it’s easy to underestimate what a bromo substituent at the right position can do. Older mentors often told me, “A bromine isn’t just a placeholder. It’s a promise you can take things further.” Compared to its chloro or iodo counterparts, the bromo version finds a sweet spot in reactivity, offering chemoselectivity with manageable byproducts. Those in the synthetic trenches appreciate fewer headaches from side reactions and less risk of over-halogenation.
Though 4-Bromo-1H-Pyrrolo[2,3-b]pyridine-2(3H)-one appears in several forms from different suppliers, most reputable sources offer it at high levels of purity, often exceeding 98 percent by HPLC or NMR analysis. My experience says trust — but verify. Regular checks reveal that batches usually ship as either off-white or light-yellow solids, with melting points consistent enough to guide reliable formulation and recrystallization during process development.
Working in both academic and industrial settings taught me to check moisture content before long-term storage. Store the material in tightly sealed amber vials under a dry atmosphere; this simple habit keeps most batches stable for years. Handling precautions mostly mirror those of similar small organic heterocycles. Always good practice to avoid inhalation or direct skin contact, and local hazard protocols cover anything beyond routine measures.
Major advancements in drug discovery rarely come from copying old scaffolds; more often, they arise by pushing distinct motifs into new territory. The core of this molecule has reappeared in several patent filings focused on oncology, anti-inflammatory, and neuroprotective therapies. Medicinal chemistry teams in my network often cite its broad compatibility with Suzuki, Buchwald-Hartwig, and Negishi reactions as a pivotal plus. This flexibility keeps new analogs flowing, even as regulatory, safety, and IP constraints tighten around older, saturated scaffolds.
Beyond the academic literature, real-world examples abound. Many big-screen combinatorial libraries rely on just such reliable, robust starting points. If you’re tasked with covering hundreds or thousands of variants for high-throughput screens, the last thing you want is a starting point that introduces impurities or side reactions. Out of the dozens I’ve run in parallel, the 4-bromo variety typically comes out near the top, keeping compound management straightforward and data interpretation clear.
The same molecular traits that turn heads in medicinal chemistry also play a role in agrochemical lead design. The fused heterocycle offers pathways toward pesticides and herbicides where metabolic stability and target selectivity go hand in hand. I’ve seen project managers switch from simpler pyridines or phenyl rings to this motif, reporting fewer off-target issues and better environmental degradation profiles. Sometimes subtle changes, like the placement of a bromine atom, ripple through to downstream activity assays with surprising impact.
Material science teams tend to focus on conjugation and charge distribution within their building blocks. This molecule, with its semi-planar core and modifiable positions, helps tailor properties from fluorescence to electron mobility. I watched a colleague’s photonics group hit a breakthrough using a similar pyrrolopyridinone, all starting from an off-the-shelf bromo analog. This isn’t about following the crowd; it’s about expanding horizons with a familiar, tweakable platform.
Beneath all the chemistry, labs face the realities of budgets and supply chains. The popularity of this scaffold means leading suppliers keep it in stock, so procurement becomes less of a project risk than chasing obscure reagents. Having sourced from various vendors over the past decade, I notice prices hover around the same range as comparable N-heterocycles, making it accessible both for academic and commercial labs. With no specialized shipping required, costs don’t spiral, which balances limited grant budgets and supports ongoing work in resource-constrained settings.
No research building block comes without challenges. The bromine substituent, while convenient, compels chemists to manage halogenated waste with care. Laboratory protocols have adapted over the years, and most institutions now enforce strict collection and disposal for halogenated solvents and byproducts. During a collaboration with an environmental health office, I saw firsthand how better communication between bench scientists and safety teams helps keep environmental impact in check. Investing in short refresher courses on waste management saves headaches and ensures that scientific progress doesn’t come at an unintended ecological cost.
Another practical challenge can arise in scale-up. A molecule that performs reliably in 50-milligram reactions might bring surprises when scaled to multi-gram or pilot-plant production. Heat transfer, mixing, and solubility all shift subtly with volume. On more than one occasion, process chemists flagged issues with batch viscosity or phase separation, easily missed at smaller scales. Experienced teams anticipate these nuances, running small pilot batches before committing to full-scale campaigns. These lessons, learned sometimes the hard way, reinforce the value of drawing on a broad network and staying connected to others who’ve run the same gauntlet before.
Anyone who’s ever sat in a project meeting knows that progress comes from problem-solving and collaboration. Discussing molecules like 4-Bromo-1H-Pyrrolo[2,3-b]pyridine-2(3H)-one, chemists compare notes on purification, scale-up, and transformation strategies. Sharing stories about what works — and what doesn’t — cuts through the marketing noise that often colors catalog descriptions. Some of my most productive late nights in the lab started with a tip from another team about a clever cross-coupling tweak or a better drying protocol. Open communication keeps the science honest and accelerates discovery in a way no product brochure ever will.
There’s growing awareness in the research community around ethical sourcing. Transparency concerning the origins of starting materials, alongside clear provenance and purity data, plays a crucial role in both compliance and corporate responsibility. Researchers have a duty, not only to their science but to the broader world impacted by their procurement choices. Over the past few years, I’ve taken the extra step to question vendors about their supply chains, environmental policies, and third-party audits. It’s not just bureaucratic diligence – it reflects a growing movement among scientists to align innovation with sustainable practices.
Modern laboratories enforce rigorous standards on chemical handling and documentation. Each time I pull a fresh vial of 4-Bromo-1H-Pyrrolo[2,3-b]pyridine-2(3H)-one from storage, it comes with paperwork detailing its origins, purity, and prior batch test results. Consistent recordkeeping means a faster path through regulatory checks and intellectual property filings. There’s a kind of peace-of-mind knowing every label and log matches real-world results at the bench. This isn’t just bureaucracy – it’s the foundation for robust, trustworthy research, especially in fields governed by strict national and international guidelines.
Experience teaches that the best way to avoid safety issues is to foster a culture where questions are welcomed, not discouraged. I make it a habit to check in with new team members whenever they handle unfamiliar compounds, sharing practical wisdom from past runs. Whether dealing with the intricacies of recrystallization or the quirks of waste disposal, everyone benefits from collective acknowledgment that no detail is too small to matter.
Continuous improvement works best when it’s built on shared experiences. In my research groups, regular “post-mortem” sessions after complex syntheses provide space for reflection — what complicates a scale-up, which purification steps proved tricky, or which suppliers offered the cleanest, best-performing product. Through open feedback, real solutions emerge:
Applying these solutions doesn’t just make work easier in the short run; it pushes the field as a whole toward more reliable, ethical, and innovative breakthroughs.
I’ve lost count of the hallway conversations that wind around the quirks and upsides of working with less-obvious scaffolds like 4-Bromo-1H-Pyrrolo[2,3-b]pyridine-2(3H)-one. Some colleagues gravitate to its versatility in fragment-based drug design, others focus on its adaptability in iterative coupling protocols, and a few appreciate the subtle boost it gives to aromatic stacking in co-crystal studies. What unites these voices is the shared recognition that this molecule, more than many in the catalog, often gives research teams room to experiment without the baggage of frailty, stubborn purification, or regulatory red tape typical of more exotic choices.
Day-to-day research in chemistry involves both inspiration and repetition. Tools like 4-Bromo-1H-Pyrrolo[2,3-b]pyridine-2(3H)-one become more than reagents; they represent a bridge between established knowledge and unknown possibilities. Their personal and collective stories shape new generations of researchers who value not just what a building block does, but how it fits into a greater project, a novel therapeutic hypothesis, or a new process innovation. Each project, each breakthrough, adds another layer to this ongoing conversation — one built on evidence, experience, and the quiet confidence of tools that help push progress forward.