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HS Code |
356084 |
| Product Name | 4-Bromo-6,7-Dimethoxyquinoline |
| Cas Number | 41398-15-6 |
| Molecular Formula | C11H10BrNO2 |
| Molecular Weight | 268.11 g/mol |
| Appearance | Off-white to pale yellow solid |
| Melting Point | 121-124°C |
| Purity | Typically ≥98% |
| Solubility | Slightly soluble in DMSO and organic solvents |
| Storage Conditions | Store at room temperature, in a tightly closed container |
| Smiles | COC1=CC2=C(C(=NC=C2Br)OC)C=C1 |
| Inchi | InChI=1S/C11H10BrNO2/c1-14-8-4-3-7-5-9(12)13-6-10(7)15-2/h3-6H,1-2H3 |
| Synonyms | 4-Bromo-6,7-dimethoxy-quinoline |
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There’s a certain satisfaction in coming across a compound that manages to clear up uncertainties in the lab, and 4-Bromo-6,7-Dimethoxyquinoline does just that for researchers in organic synthesis and materials science. In my experience, it’s not often that a specialty compound answers to so many experimental needs, but this one fits into common workflow without hidden complications. It can make a difference for those working on new molecular scaffolds or needing reliable intermediates when exploring heterocyclic frameworks.
Each lab run works best with solid building blocks. 4-Bromo-6,7-Dimethoxyquinoline carries a combination of bromo substitution at the fourth position and methoxy groups at the sixth and seventh positions on its quinoline backbone. The presence of bromine isn’t just a cosmetic touch — bromine substitutions often allow further transformations through palladium-catalyzed coupling reactions, such as Suzuki or Buchwald-Hartwig, which have become staple tools in research groups tackling complex organic syntheses. Compared to non-halogenated analogs, this compound opens up more room for cross-coupling chemistry, which can save both money and time for the experienced chemist.
Peering closer at the structure, those methoxy groups aren’t there just for show either; they add a touch of electron-rich character to the molecule, adjusting reactivity and sometimes helping to stabilize certain intermediates. This means less headache when developing new pharmaceuticals or advanced materials, where modifying a molecular scaffold makes all the difference between a dead end and a breakthrough.
Looking beyond the label, it pays to know the technical details. 4-Bromo-6,7-Dimethoxyquinoline has a molecular formula of C11H10BrNO2. The molecular weight comes in at about 268.11 g/mol. I’ve learned to appreciate reliable melting points in determining batch purity, and this one’s melting range typically lands between 119°C to 122°C under standard conditions. In terms of appearance, it often comes as a pale yellow to off-white crystalline powder, and stores well in a dry, dark container — pretty straightforward in the chemical storeroom, as long as it’s kept away from strong oxidizers and moisture sources.
Solubility is a practical concern. 4-Bromo-6,7-Dimethoxyquinoline dissolves well in organic solvents like DMSO, DMF, and chloroform. It shows low solubility in water, which is no surprise for quinoline derivatives, but this quality can actually help when it’s applied in biphasic reaction systems where you want to extract your product away from reaction side-products.
Versatility often makes or breaks the reputation of a chemical. Here the compound serves a wide range: drug discovery, dye precursor development, agrochemical research, and advanced organic electronics all benefit from chemistry on this scaffold. My own time in the lab saw this compound slide seamlessly into several medicinal chemistry campaigns, either as a core structure for kinase inhibitor exploration or as a bridge to more elaborate heterocyclic arrays. Having a bromine atom in the right spot offers researchers a handle for functionalization, which brings a lot of value when tweaking pharmacophores for desired biological activity.
In drug R&D, functionalization at the fourth position has repeatedly helped teams introduce new substituents, enabling rapid design-make-test cycles. The methoxy groups on positions six and seven also change the shape and polarity of the molecule, nudging selectivity and bioavailability in the right direction. Chemical suppliers have noticed the steady demand in medicinal chemistry, which likely drove improved access to high-purity grades.
Materials chemists have also taken to 4-Bromo-6,7-Dimethoxyquinoline. With conjugated electron systems, it plays a supporting role in the synthesis of liquid crystal materials, organic semiconductors, and photoluminescent compounds used in diagnostic imaging or optoelectronic devices. Unlike some alternatives, the presence of both bromine and methoxy groups can tune the optical and electrical properties, and there’s no need for overly complex multi-step protection and deprotection strategies.
Taking a closer look at the research literature, hits on 4-Bromo-6,7-Dimethoxyquinoline aren’t just isolated to industry; academic groups cite the compound in studies addressing antimicrobial agents, anti-cancer scaffolds, and even potential treatments for neurological disorders. In these settings, productive synthetic routes must balance cost, ease of handling, and reliability of structure. The compound stands out for its stability and clean reaction profiles with common palladium or copper-catalyzed coupling systems, which keeps troubleshooting to a minimum. Purification after coupling steps usually goes as predicted, with little in the way of troublesome byproducts.
Now, not every compound with attractive properties finds its place in routine use. The reason 4-Bromo-6,7-Dimethoxyquinoline sees consistent demand connects to its reliability in key coupling reactions — it resists rapid oxidation, and its crystalline form is easy to weigh, dissolve, and recover. Having worked with other bromo-quinolines that gave off-putting odors or decomposed on the bench, I understand how a stable, easy-to-handle intermediate quickly becomes the “first reach” for experienced researchers. Routine matters more than theory when the grant charts call for new results with fewer setbacks.
4-Bromo-6,7-Dimethoxyquinoline offers practical differences over similar compounds. For starters, the dual methoxy substitution on the aromatic ring alters both its reactivity and its fate in biological and electronic systems. Many related bromoquinolines lack these groups, which reduces their synthetic flexibility and lowers their potential in specialized applications.
Some researchers have considered 4-bromoquinoline or 6,7-dimethoxyquinoline as alternatives, but that split in substitution pattern makes a significant impact. Without a bromine atom at the fourth position, cross-coupling options reduce sharply; without the second methoxy, the molecule usually shows less fine-tuned interaction when probing enzyme binding sites or forming ordered films in device applications. The specific balance found here between electronics, shape, and substituent position is why so many synthetic projects have adopted it as a go-to intermediate.
From a safety perspective, 4-Bromo-6,7-Dimethoxyquinoline boasts reasonable handling characteristics compared to some of the more pungent, unstable, or moisture-sensitive heterocycles. Labs aiming to streamline their workflow and minimize hazards can incorporate it without much procedural change, assuming the usual precautions for organic halides and aromatic amines are observed.
As with many specialty reagents, challenges cluster around sourcing and scale-up. Costs sometimes rise when global supply chains tighten, and unpublished synthetic details can slow forward progress in the hands of students or less experienced team members. Still, open research and shared protocols have made this chemical much more accessible than in the past, and more vendors now offer it in research-grade quantities with full certificates of analysis and spectral data.
There’s also an ongoing push for greener, less wasteful chemistry in synthetic labs around the world. The typical routes for preparing functionally substituted quinolines use precious metal catalysts and halogenated solvents, which draw scrutiny both for cost and for their environmental impact. A few research groups are tackling these issues head-on — switching to reusable catalysts, optimizing solvent use, and using continuous flow conditions to minimize waste. These changes do more than tick regulatory boxes; they speed up runs, lower overhead, and make chemists proud to stand behind their work. Demand from the pharmaceutical and fine-chemicals sectors has helped drive supplier adoption of sustainable processes, narrowing the price gap while retaining high purity.
Another practical issue emerges during storage and long-term use. Like many aromatic bromides, 4-Bromo-6,7-Dimethoxyquinoline responds poorly to careless exposure to light and moisture. Over the years, I’ve seen more than a few cases where unreliable storage practices led to diminished yields or, worse, failed reactions. Fortunately, modern packaging — amber glass with airtight seals — keeps the compound stable for extended periods. Labs can avoid losses simply by setting rules: store it dry, keep out sunlight, and check for purity before critical runs. Following those steps brings peace of mind especially during high-stakes projects.
Focusing on laboratory safety, standard precautions for handling aromatic bromides and quinolines apply. I once saw a project delayed for weeks when a team overlooked compatibility with basic personal protective equipment, so it’s smart to always use gloves and safety glasses, along with common sense in fume hoods. Monitoring potential exposures — both through skin and via vapors — is basic practice in chemical synthesis. Most regulatory agencies do not classify this compound as a severe health hazard, but any user must respect the risks that follow quinoline-based chemistry, including potential sensitization and mild irritant effects.
On the regulatory side, 4-Bromo-6,7-Dimethoxyquinoline doesn’t show up on major watchlists, so research labs rarely run into restrictions when sourcing it for standard chemical synthesis. Regular audits and up-to-date safety data sheets ensure compliance with institutional and local guidelines. This relative freedom keeps momentum going, especially compared to more heavily restricted aromatic halides, and allows researchers to prioritize scientific creativity rather than endless paperwork.
A decade in and out of academic and startup labs has shown me the difference brought by a compound that works without complaint. The challenges facing pharmaceutical and materials scientists have grown more complex every year, driven by tighter timelines and greater regulatory scrutiny. In this environment, reliable building blocks — those that do what the literature promises, in every bottle and every batch — prove their worth. 4-Bromo-6,7-Dimethoxyquinoline has earned its spot on the shelf because it solves more problems than it causes.
Seeing growing adoption for new applications is encouraging. Recent years have seen demand rise from organic electronics designers, thanks to the compound’s favorable optoelectronic properties when embedded in conjugated systems. Dye chemists also value its substitution pattern for building blocks in fluorescent tag development. In the agrochemical field, certain patented herbicides and fungicides depend on similar quinoline combinations, underscoring the broad reach of compounds like this one.
Peering into the near future, I see more labs shifting towards advanced automation in synthesis, screening, and purification. Compounds like 4-Bromo-6,7-Dimethoxyquinoline fit neatly into these workflows because they show reliable, reproducible behavior no matter the scale. These features matter in an era where each experiment faces both budget and reproducibility challenges. Students and experts come back to these trusted scaffolds because the learning curve is short and the benefits endure.
To stay in step with sustainable chemistry goals, chemical suppliers and researchers alike should continue looking for opportunities to cut down on waste, improve process efficiency, and select reagents with robust safety profiles. Supporting these goals with real-world decisions in procurement, storage, and waste management means more scientific progress, less downtime, and a stronger case for new funding and partnerships.
So, 4-Bromo-6,7-Dimethoxyquinoline shows its true value by letting people move quickly from idea to experiment without unnecessary headaches. Compared to similar options, its particular mix of stability, reactivity, and compatibility with trusted reactions gives researchers a steady way forward. It isn’t flashy, but it gets the job done where it matters. Scientists that have spent time troubleshooting fickle intermediates know the relief a dependable compound brings. With changing technology and a steady march toward greener chemistry, this compound’s reputation will only strengthen. The coming years promise new applications, a push for even safer, cleaner production, and continual improvements driven by those who value real-world results more than buzzwords or trends.