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HS Code |
464228 |
| Chemical Name | 3,6-Dibromopyrazine-2-carboxylic acid |
| Cas Number | 144398-98-5 |
| Molecular Formula | C5H2Br2N2O2 |
| Molecular Weight | 297.89 g/mol |
| Appearance | White to off-white solid |
| Melting Point | Above 250°C (decomposes) |
| Purity | Typically ≥98% |
| Solubility | Slightly soluble in water; soluble in DMSO and DMF |
| Storage Temperature | Store at 2-8°C |
| Smiles | C1=NC(=C(N=C1Br)Br)C(=O)O |
| Inchi | InChI=1S/C5H2Br2N2O2/c6-2-1-8-4(5(10)11)3(7)9-2/h1H,(H,10,11) |
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3,6-Dibromopyrazine-2-carboxylic acid offers a solid base for pushing new boundaries in organic synthesis. Having handled and discussed this precise molecule with research teams and process chemists, I see a compound that offers more than what sits on the surface. It contains a distinctive pyrazine core decorated with two bromine atoms at positions three and six, and a carboxylic acid at position two. This structure might sound straightforward, yet it supports a remarkable range of transformations, building versatility into applications that stretch from academic research to pharmaceutical development.
Looking at its formula, C5H2Br2N2O2, and with a molecular weight of about 295.89 g/mol, the compound stands out as one that balances reactivity and stability. Many who have worked in the field know that halogenated pyrazines serve as gateways to advanced molecules, especially when selective substitution is critical for the route. 3,6-dibromopyrazine-2-carboxylic acid does not follow the trail blazed by more common mono-brominated analogs, and its dual bromine arrangement provides more entry points for further functionalization. That opens up synthetic routes which help in the preparation of sophisticated anti-infective agents, agrochemical scaffolds, or advanced materials.
I remember sitting in a lab during a late-night experiment, testing building blocks for metal-catalyzed cross-coupling reactions. Many pyrazines bog down projects when they fail to provide enough versatility. Introducing this dibromo variant changed the pace. The bromine atoms enable efficient Suzuki and Sonogashira reactions, where creating carbon-carbon or carbon-nitrogen bonds with precision determines the progress of the overall project. With this compound, the difference is more than subtle. It marks the switch from struggling to find a suitable intermediate to having a solution that opens up a suite of possibilities.
Pharmaceutical labs often demand subtle modifications to core scaffolds, especially when fine-tuning biological activity. Researchers who’ve tried tweaking mono-brominated pyrazine carboxylic acids know how stubborn these molecules can get. The mono-bromo version only allows a single spot for upgrade. Add the second bromine, and everything changes. Each bromine lets a chemist place new groups where needed, with the carboxylic acid acting as both a reactive handle and a site of solubility enhancement. In my own screening work, I’ve seen 3,6-dibromopyrazine-2-carboxylic acid not only streamline the synthesis of potential kinase inhibitors but also allow for quick analog generation, making structure-activity relationship studies faster and more robust.
Some might ask how this compound stacks up against more basic starting materials. Many who’ve worked with plain pyrazine derivatives bump into issues with selective functionalization. Trying to get more than one halogen in just the right spot can get tedious and wasteful. Excess steps mean more solvents, more reagents, and bigger costs. With this dibrominated acid, you get a shortcut. Its direct preparation means fewer purification headaches and less environmental burden, especially since carboxylic acids lend themselves to straightforward crystallization.
In practical laboratory terms, comparing this compound to its less brominated or mixed halogen siblings is almost unfair. I recall hearing from a senior chemist who spent weeks wrestling with 3-bromopyrazine-2-carboxylic acid, trying to introduce that second critical point of variation. Purity plummeted, byproducts piled up, and the yield dipped below 30 percent. Switching to the ready dibromo acid solved the problem in two days and gave crystalline material that could go straight to the next step.
Let’s not gloss over one of the biggest wins: functional group tolerance. The carboxylic acid resists reduction under standard cross-coupling conditions, holding its ground where alternatives cannot. This property allows the inclusion of sensitive partners, broadening the synthetic toolkit for medicinal chemistry dives. In my own workflows, I’ve managed to prepare not just simple substitution products, but also complex, branched molecules—an achievement that takes too much troubleshooting with other pyrazine acids. This level of flexibility drops the risk of synthetic dead ends.
The science world never settles for just “it works.” Pyrazine fragments have a long history, from setting nitrogen-rich backbones for antibiotics to providing heterocyclic features in luminophores and dyes. Methotrexate, clofazimine, olaparib—these medicines all owe part of their activity to nitrogen-dense rings. Pyrazine-2-carboxylic acids find themselves in lead development cycles again and again, particularly as pharmaceutical projects hunt for new kinase inhibitors and antimicrobial scaffolds. The dibromo version makes that journey shorter. Both bromines offer immediate handles for tuning the electronic environment, shifting binding profiles, or sticking on solubilizing units. It’s not just about quick wins; it’s about accessing structures that might be impossible with older chemistry.
Materials scientists also see value in pyrazine building blocks as platforms for electronic and optical applications. The dibrominated structure brings a heavier halogen presence, which changes thermal and conductive properties when built into polymers or small-molecule films. In personal discussions with electronics researchers, many prefer bromo derivatives for precision placement in molecular wires, especially as they work toward greater performance in organic solar cells or light-emitting diodes.
Trusting the source of specialty chemicals became even more important over the last decade. Stories float around about research projects delayed by impurities in heterocycles. Not all manufacturers invest the time or resources to deliver true analytical-grade 3,6-dibromopyrazine-2-carboxylic acid. The most respected vendors test for halide impurities, residual solvents, and metal traces, confirming each batch against NMR, HPLC, and mass spectrometry results. This attention to verification takes stress off the research process. Having walked through quality walkthroughs at both large suppliers and boutique labs, I can spot inconsistencies that lesser sources ignore—variations in melting point, solubility problems, or contamination by dibromo isomers.
In regulatory spaces, the importance of traceability cannot be overstated. Agencies continue pressing for documentation, purity, and robust safety profiles, not just in pharma but in advanced tech industries. The carboxylic acid moiety also means the molecule meets specifications for further derivatization through standard amide bond formation, esterification, or salt formation without introducing unpredictable side products. This predictability matters for scaling up reactions from the milligram level in the lab to larger preclinical or even pilot-plant scale reactions.
I’ve handled a wide range of heterocycles, and the temptation to go for cheaper mono-halogenated pyrazines pops up every now and then. Still, every shortcut I’ve seen pursued with these cheaper materials ended up costing more in time or quality. The purification step after introducing a second halogen, especially if positional isomers can form, regularly defeats even experienced teams. Project managers notice—timelines slip, budgets grow, and, above all, excitement fades.
Contrast that with projects using 3,6-dibromopyrazine-2-carboxylic acid from the outset. Substitution reactions run without lengthy re-optimization. Analytical verification tends to confirm expectations early, reducing risk for downstream biological testing. Mixtures are cleaner, and product isolation doesn’t become a marathon. Even in non-pharma fields, having the dibromo arrangement means more options for sensor attachment or dye modification, which comes in handy in analytical chemistry and materials science.
Take the electronics field for example. Pyrazine-based fragments enhance the electron affinity of polymers, which becomes even more pronounced with heavy atom substitution. The dibromo variant lets researchers anchor bulky side chains or electron-acceptor units exactly where needed. That precision makes a direct impact on conduction pathways in organic circuits. Across applications in catalysis, dye-sensitized solar cells, or even specialty pigments, the story repeats itself: starting with the right building block pays off down the line.
Any seasoned chemist treats halogenated organic acids with a blend of curiosity and respect. While 3,6-dibromopyrazine-2-carboxylic acid doesn’t belong in the “unstable” or “explosive” category, it demands proper handling like any reactive heterocycle. Standard good practice applies—gloves, eye protection, and the right ventilation setup—which many researchers already follow without thinking. A compound of this type enters the equation of environmental compliance discussions, so discussions about waste management and solvent use follow soon after. My experience has taught me that thoughtful planning—using minimal volumes, applying chromatography only when necessary, and neutralizing residues—keeps projects both safe and sustainable.
Working with dibrominated molecules means confronting the question of bromine sources and disposal. In research environments shifting toward green chemistry, teams value the ability of this molecule to enable convergent synthesis, dropping the number of side reactions and avoiding multiple halogenation steps that generate hazardous byproducts. Less waste, fewer steps—the environmental math ends up positive.
Pyrazines keep evolving with new demands from science and industry. The track record of 3,6-dibromopyrazine-2-carboxylic acid has pushed research forward in my own work and in labs I’ve visited worldwide. Medicinal chemistry thinks long-term, as does materials science, and the necessity of robust, versatile, and straightforward intermediates will only grow.
Whether driving innovation for new therapies, customizing dyes and sensors, or tuning the backbone of high-tech materials, the dibrominated acid proves itself time after time. Its regular presence in journals and patents speaks to industry confidence. Over the years, watching the reputation of this molecule grow has confirmed that strategic choices in building block procurement create ripples across whole industries—reducing cost, expanding experimental opportunity, and cutting down on environmental impact.
Drawing from years of workbench trial and error, I have a few recommendations. Plan your project around the unique reactivity the two bromine atoms provide. Exploit orthogonality—in other words, introduce different groups at each bromine for rapid analog development. Couple this with selective amide or ester formation from the acid, and you’ll cover a broad swath of chemical space without needing to redesign your synthetic plan halfway through.
Stay vigilant about purity and documentation, especially if you’re scaling toward applications that demand quality by regulation. Develop a relationship with suppliers who deliver consistency—don’t gamble with batches from unknown sources, since subtle impurities at the building block stage often grow into major headaches by the characterization phase.
For those engaged in green chemistry, consider using catalytic or low-waste procedures to explore the full suite of cross-coupling and functionalization reactions available to this compound. Not only will that keep the regulatory and environmental reporting simple, but results can be more reproducible and transferable across teams facing similar challenges.
From hands-on synthesis to project leadership, my experience has taught me this lesson: the right choice of building block like 3,6-dibromopyrazine-2-carboxylic acid carries proven benefits long past the order and delivery stage. It fills an important role in modern organic synthesis—precisely where flexibility, efficiency, and reliability are in short supply. Few molecules so consistently earn both the trust and respect of their users, from medicinal chemists hoping to quicken the pace of discovery, to materials scientists building the next generation of functional devices.
Those who work with this compound understand its value. It transforms what could become a synthetic grind into a streamlined progression, shortens timelines, and raises the standard of what’s possible. By opting for 3,6-dibromopyrazine-2-carboxylic acid, labs empower their teams to try things they otherwise might set aside as too complex. That means broader horizons in research, speedier routes from hypothesis to product, and a renewed sense of satisfaction every step of the way.