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HS Code |
553371 |
| Chemicalname | 7-Bromo-8-Methylquinoline |
| Casnumber | 872365-14-5 |
| Molecularformula | C10H8BrN |
| Molecularweight | 222.08 g/mol |
| Appearance | Off-white to yellow solid |
| Meltingpoint | 68-72°C |
| Solubility | Soluble in organic solvents (e.g., DMSO, chloroform) |
| Purity | Typically ≥97% |
| Iupacname | 7-bromo-8-methylquinoline |
| Smiles | Cc1cccc2ccnc(Br)c12 |
| Inchi | InChI=1S/C10H8BrN/c1-7-4-3-6-2-5-12-10(11)9(6)8(7)7/h2-5H,1H3 |
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Anyone who’s spent time working with heterocyclic compounds knows how certain molecules quietly shape research momentum. 7-Bromo-8-Methylquinoline, with its thoughtful structural design, has found a solid role in advancing organic synthesis, pharmaceutical research, and analytical chemistry. Over the past decade, I’ve watched attention shift toward these quinoline derivatives, not just for academic curiosity, but because they offer a handle on selectivity and reactivity that makes troubleshooting in the lab significantly less painful.
Every bottle of 7-Bromo-8-Methylquinoline I’ve opened brought the same crisp sense of expectation—off-white to pale yellow crystalline powder, stable under room conditions, and non-hygroscopic, which means it won’t unexpectedly clump up. With a molecular formula of C10H8BrN and a molar mass just north of 222 g/mol, each aspect of its structure has downstream effects. The bromine atom sitting at the seventh position is not added just for show; it alters electron density in a way that opens up otherwise tricky substitution pathways. In my own work, even modest differences in purity—above 98% by HPLC, for instance—meant the difference between a clean product and a batch with nagging impurities that take hours to debug. In early-stage pharmaceutical research, high-purity material cuts down wasted cycles and builds trust in downstream data.
The world of quinolines can feel crowded. Start scanning catalogues and the shelves fill up with positional isomers and analogs—some methylated, some halogenated, others fused with various functional groups. Through experimentation, I found that swapping a bromine out for a fluorine, or nudging the methyl group over to a different ring position, shifts everything—solubility, reactivity, even the kind of side reactions that show up. 7-Bromo-8-Methylquinoline brings together two features that stand apart: the electron-withdrawing bromine, which guides electrophilic substitution, and the methyl at the eighth spot, which helps nudge selectivity in favor of less congested sites. These tweaks may sound small, but in building a target molecule, a missed regioselective reaction leads to headache after headache. This compound, then, isn’t just another line in the catalog—it shows the power of strategic substitution in molecular design.
In the rush to chase novel active pharmaceutical ingredients, intermediates like 7-Bromo-8-Methylquinoline become the backbone of whole drug discovery programs. Scientists exploring anticancer agents, antimalarial scaffolds, or other therapeutic classes turn to precisely these frameworks. Based on conversations with formulation chemists and several years of my own small-scale syntheses, this compound stands out in Suzuki–Miyaura and Stille coupling reactions. Here, the bromine moiety acts like a hand-shake for palladium catalysts, enabling clean cross-coupling with various boronic acids to create new carbon–carbon bonds. A methyl group perched at the eighth position influences the electronic environment, lowering activation barriers and boosting yields compared to unsubstituted quinolines. For medicinal chemists mapping out a library of analogs, the time saved here adds up to weeks over a yearlong project cycle.
I’ve also seen this compound show up in materials chemistry, pressed into service for fluorescent probes or in early-stage OLED research. Structural tweaking of the quinoline backbone, especially through halogen – methyl pairing, often tunes photophysical properties, giving research groups an accessible starting point for new dye designs. Unlike some highly functionalized alternatives that suffer from limited stability or rare precursor feedstock, 7-Bromo-8-Methylquinoline offers a blend of commercial availability and robust shelf life, which makes trial-and-error work less risky.
The toughest days in the lab often come from slogging through purification protocols after an ambitious reaction. My own introduction to quinoline derivatives involved endless chromatographic tweaking—tracking down what felt like hundreds of tiny, persistent side products. With 7-Bromo-8-Methylquinoline, as long as the upstream reagents are dry and standard protocols are tightened up, the crude material comes out distinctly easier to clean up. Fewer polar byproducts and a sharp melting range—typically close to literature values—mean less second-guessing over purity. In contrast, related compounds like 8-methylquinoline (the unsubstituted parent) or 7-fluoro derivatives can introduce more noise because of their greater volatility or unpredictably reactive intermediates. Better selectivity here translates into purer final products and a more streamlined workflow, freeing up resources for actual research instead of endless re-purification cycles.
Every scale-up brings new challenges. Bench-scale batches may look promising, but kilo lab synthesis doesn’t always play by the same rules. 7-Bromo-8-Methylquinoline holds up through these transitions, thanks to its physical robustness and relative insensitivity to air or moisture. In my own industry consulting, I’ve watched otherwise promising projects stumble because an intermediate decomposed just fast enough to clog reactors or layered environmental headaches onto simple process steps. This compound’s stability means it moves through standard storage and handling protocols without expensive workarounds like nitrogen blankets or elaborate drying. Those savings become the difference between a commercially viable project and one that stalls out before launch.
Even specialty CROs and CDMOs reach for 7-Bromo-8-Methylquinoline when tasked with exploratory syntheses. Yields stay consistent across scales, and its compatibility with both batch and flow conditions makes it a flexible candidate for continuous manufacturing setups. Compared to some of the heavily fluorinated or oxygenated quinolines, which often demand customized glassware and tight-wound environmental controls, the bromo-methyl compound fits in with a standard toolkit. This flexibility matters to any team balancing timelines and cost control.
Almost every synthetic chemist I know could rattle off a list of failures blamed on poorly chosen intermediates. It’s not just about following the literature, but really digging into the quirks of each molecule. I remember a series of trials using 7-chloro-8-methylquinoline in coupling reactions, only to find that the chloro group lagged in reactivity, chipped away at yields, and left behind a handful of intractable byproducts. Swapping in the bromo derivative solved half the headaches overnight—the bromo group’s larger atomic radius and higher leaving group capacity suits most modern palladium-catalyzed reactions.
Variations with other substitutions—like sulfonates or amines—either raise the cost or create additional regulatory headaches due to toxicity profiles. The simple yet effective structural combination found in 7-Bromo-8-Methylquinoline balances availability and versatility while sidestepping the more difficult regulatory barriers tied to heavier halogens or exotic functional groups. Hard-earned experience shows that smart design, not just novelty for novelty’s sake, leads to better project outcomes.
Every new synthetic intermediate carries responsibilities, not just for project success but broader concerns about lab safety and environmental stewardship. I’ve always appreciated that 7-Bromo-8-Methylquinoline follows the playbook of many mid-size aromatic heterocycles—non-volatile, non-explosive, and relatively low acute toxicity. Lab safety audits tend to pass smoothly when proper glove and fume hood protocols are followed. This track record stands in sharp contrast to some less stable, more reactive quinoline derivatives that can turn simple benchwork into a minefield of waste management issues.
Teams focused on green chemistry or sustainable process design won’t find this molecule an obvious villain. Brominated aromatics occasionally draw attention for environmental persistence, and routine procedures should always include careful waste segregation. In my experience, its stability keeps accidental releases to a minimum, and modern waste disposal protocols easily handle the small quantities present in most academic and pharmaceutical research. Synthetic strategies based on this compound fit well with both established and next-generation green chemistry metrics, especially when paired with cross-coupling partners designed for low-persistence and minimal ecological footprint.
Reliability builds reputations in research, not just publications. Across a range of synthetic challenges, from candidate library synthesis in pharma startups to late-stage derivatization for imaging probes, I’ve watched researchers return to 7-Bromo-8-Methylquinoline because it does the small things right. Each milligram represents a pathway to high-value target molecules—a clean substrate in a crowded field.
Compared to more exotic functionalized heterocycles—oftentimes sourced in limited quantities or with erratic batch quality—this compound consistently shows tight lot-to-lot variation. That reliability means less guessing, less batch-specific revalidation, and cleaner transitions between research phases. Project managers and chemists alike gain more control over resource allocation and project timelines.
Let’s talk structure. Placing bromine at the seventh position on the quinoline scaffold delivers more than a synthetic convenience. The atom’s size and polarizability directly impact reactivity in key cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig, and Heck transformations. The presence of a methyl group at position eight isn’t random—a strategically placed electron donor, it nudges electron density precisely where synthetic chemists want, influencing regiochemistry and providing a measurable boost in coupling efficiency. All this adds up to fewer side products, greater yield reliability, and more successful scale-ups.
Other common alternatives, like 7-chloro- or 7-iodo-derivatives, stumble in different ways. Chlorine, less reactive, slugs through many catalysts and wastes time. Iodine, while highly reactive, brings storage headaches and greater expense, not to mention a softer environmental performance profile. The bromo-methyl combination strikes a balance many in the industry have grown to trust.
Any researcher who’s spent long hours at the bench knows the importance of reliable starting materials. Projects develop their own momentum when researchers don’t have to second-guess their substrates. In development teams I’ve consulted with, the move to 7-Bromo-8-Methylquinoline almost always meant faster troubleshooting; fewer phone calls to troubleshoot unstable reagents and more conversations about actual scientific challenges. For every hour saved on routine prep, teams have more time and energy for discovery.
The discussions I’ve observed on academic forums, industry roundtables, and cross-company collaborations reveal a shared appreciation for tailored, well-characterized intermediates like this. They don’t command the glamorous reputation of blockbuster drugs or new catalysts, but lay the intellectual foundation for those breakthroughs.
While 7-Bromo-8-Methylquinoline already fits comfortably into many research programs, ongoing innovation could focus on even greener synthesis routes and expanded applications. From an insider’s view, it remains important to prioritize raw material traceability and to narrow down synthesis byproducts even further. Stakeholders—lab managers, procurement leads, and process engineers—benefit by demanding transparent sourcing and full analytical characterization, ensuring even more consistent research output.
In conversation with process development chemists, I’ve noticed a drive to shift toward milder cross-coupling conditions, seeking to lower energy use and minimize precious metal catalyst waste. 7-Bromo-8-Methylquinoline’s proven compatibility with modern ligand systems means future efforts can focus on experimentation—optimizing greener solvents, making use of flow reactors, and decreasing energy footprints. Strategic research funding and internal training drive adoption of better protocols. This cycle—improving how intermediates are prepared, handled, and used—should propel research toward more sustainable, cost-effective outcomes.
Those designing the next generation of synthetic intermediates would do well to look at the track record built around this compound. Emphasizing practical chemistry over theoretical flashiness, its day-in, day-out value emerges through the shared experience of bench scientists and project managers alike. Far from a niche reagent, it stands as a quiet standard-bearer, pointing the way for accessible, scalable, and responsible innovation.