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HS Code |
870935 |
| Chemical Name | 2-Fluoro-4-Bromo-5-Chloronitrobenzene |
| Molecular Formula | C6H2BrClFNO2 |
| Cas Number | 349535-94-2 |
| Appearance | Pale yellow solid |
| Melting Point | 62-65°C |
| Solubility | Slightly soluble in organic solvents |
| Purity | Typically >98% |
| Storage Conditions | Store in a cool, dry place, away from light |
| Synonyms | 1-Bromo-3-chloro-4-fluoro-2-nitrobenzene |
| Smiles | C1=C(C(=C(C(=C1Br)Cl)[N+](=O)[O-])F) |
| Inchi | InChI=1S/C6H2BrClFNO2/c7-3-1-4(8)6(10(11)12)2-5(3)9/h1-2H |
| Hazard Statements | Harmful if swallowed, causes skin and eye irritation |
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Living as a researcher means working through shelves lined with bottles whose names take some effort to pronounce, but every so often, a chemical stands out. 2-Fluoro-4-Bromo-5-Chloronitrobenzene is one of those. In labs where synthesis isn’t just a job but a passion, this compound nudges innovation forward. Not because it’s a showpiece or a common tool, but for the specific kind of flexibility and reactivity it brings to the bench.
I’ve seen plenty of benzene rings coming through research projects, each with their own quirks. The set of substituents in 2-Fluoro-4-Bromo-5-Chloronitrobenzene—a fluorine, a bromine, a chlorine, and a nitro group in select positions—creates a backbone primed not just for one purpose but a range of potential syntheses. A skilled chemist recognizes how these halogens don’t just sit idle; they control how the ring behaves in reactions, giving an edge when building more complex molecules. Whether you’re targeting medicinal scaffolds, exploring agrochemical leads, or pushing academic curiosities, this molecule’s pattern offers predictability alongside opportunity.
The fluorine atom at position 2 tends to bring about unique electronic effects. In practical terms, it can drive selectivity in nucleophilic aromatic substitution or affect the biological activity of end-products. Bromine at position 4 means possibilities for cross-coupling strategies. Suzuki-Miyaura or Heck reactions, for example, gain a boost from brominated rings, providing ways to hook new groups onto the structure with decent reliability. Chlorine at position 5 lets the molecule stay recognizable yet distinct—its presence not only aids identification but also imparts different chemical reactivity compared to a simple di-halogenated ring. Topping it off, the nitro group at position 5 gives the molecule an electron-withdrawing center, stabilizing certain intermediates and impacting the overall reactivity from the start.
From my work in pharmaceutical research, I learned early on that precious yields come not just from what a molecule looks like but what you can make out of it. With 2-Fluoro-4-Bromo-5-Chloronitrobenzene, researchers often move beyond bench-scale curiosity. In the last five years, you’d have seen its application ranging from early-phase drug discovery to specialty dye synthesis. For teams tackling small molecule drugs, modifying the benzene ring can tweak a candidate’s bioavailability, stability, or target affinity. The arrangement of substituents on this compound allows for stepwise replacements, polar modifications, and late-stage functionalizations—tools medicinal chemists hold close.
Academic labs favor this molecule for its adaptability in aromatic substitution experiments. Multistep syntheses often need intermediates that behave reliably, even as conditions shift from strongly acidic to basic or through temperature swings. In my experience, halogenated nitrobenzenes like this one have survived rough handling during undergraduate experiments, hinting at general robustness. For undergraduate instruction or advanced research, this means more time spent learning and less time troubleshooting decomposed products.
The specialty chemicals sector finds further value in molecules with both halogens and nitro groups. Fluorinated aromatic compounds serve in manufacturing advanced materials, like liquid crystals and high-performance polymers. Adding bromine or chlorine into the mix brings opportunities for molecular fine-tuning, helping tweak thermal properties and mechanical strength. Paints, pigments, and specialty coatings have profited from such compounds, not just for their color properties but their stability and effectiveness against environmental wear.
Walking through a catalog, you might spot plenty of other halogenated nitrobenzenes. I have used 2,4-dibromo-5-nitrobenzene and its fluoro-analogs for different syntheses, but few offer the same selective pattern of halogenation as 2-Fluoro-4-Bromo-5-Chloronitrobenzene. Drop either the fluorine, bromine, or chlorine, and you get a molecule that maybe feels easier to handle, but less flexible down the line. Halogen patterns shape reactivity; the specific substitution here allows access to a broader set of derivatives.
Compared to its close cousins, this molecule holds onto a certain complexity. Simple monohalogenated nitrobenzenes are cheaper, run with less fuss in elementary reactions, and find use as test substrates in methodology papers. But as synthesis pushes from routine to ambitious, the options for stepwise halogen exchange, selective reduction, or cross-coupling multiply. That’s where the three-way-division of halogens and a single, strong nitro group makes a difference.
Handling is another point worth bringing up. Brominated and chlorinated aromatics can emit strong odors or prove hazardous if not handled correctly. After working through a few scale-ups with comparable compounds, I’ve noticed that adding a fluorine atom tilts the balance—raising the boiling point and affecting solubility. Results in the lab become more predictable. Such small chemical shifts pay off when purification steps drag on, or when chromatography stops being routine and starts eating into your month’s progress.
I have come across the application of 2-Fluoro-4-Bromo-5-Chloronitrobenzene in the formation of molecular building blocks for organic electronics. Sourcing reliable intermediates remains a headache for startups pushing into new material platforms. With big pushes for flexible displays and new light-emitting materials, a compound that’s both reactive and stable is a strong asset. The presence of the nitro group brings electron-withdrawing strength, while multiple halogens allow precise tuning, letting material scientists adjust charge transport properties in organic semiconductors.
Even outside cutting-edge technology, this molecule finds its spot in the hands of chemical biologists attempting to map new pathways in drug metabolism. Radiolabeling, for instance, relies on compounds that can accept isotopic versions of chlorine, bromine, or fluorine—this compound provides the scaffold ready-made. In radiotracer synthesis, reliability at each substitution step keeps costs and errors in check. The importance becomes clear once a day’s work relies not on scale but on a handful of milligrams, each step counted against tight research budgets.
Young researchers often ask why we fuss about specific atoms on the benzene ring. Over years spent in synthesis labs, it’s become clear that properties come not just from the types of groups but their arrangement. The para, ortho, and meta split changes not just the look of a chemical structure diagram, but how that molecule enters into next-step reactions. In 2-Fluoro-4-Bromo-5-Chloronitrobenzene, spatial relationships guide incoming nucleophiles, dictate reduction pathways, and even affect the speed at which reactions unfold.
Chemists who have spent long days with trial-after-trial know that the difference between a working synthesis and a failed one can be a single substituent on a ring. Swapping out a fluorine for a hydrogen isn’t just a matter of changing names; suddenly, yields might drop, purification could become a nightmare, or the resulting compound sees its biological action disappear. Specificity—here in the arrangement of fluorine, bromine, chlorine, and nitro—makes success more repeatable.
Safety and reliability matter when a research budget hovers on the edge. Having experienced both the failure of unstable intermediates and the peace-of-mind that comes from robust starting materials, I hold appreciation for molecules that keep their structure under pressure and diverse conditions. 2-Fluoro-4-Bromo-5-Chloronitrobenzene doesn’t just provide versatility; it excels in keeping contaminant rates low and batch-to-batch variation minimal.
Many of us have opened a bottle and wondered about purity. Problems with isomer contamination or unwanted byproducts can complicate downstream analysis and biological evaluation. The sharp separation among its halogen and nitro containers means easier chromatographic purification and sharper peaks in analysis. That’s valuable from both an economic and a regulatory perspective. Analytical reproducibility means less time explaining unexpected results and more time focusing on true experimental outcomes.
Any discussion on chemicals like this one cannot ignore environmental issues. Chemical manufacturers face tightening regulations about halogenated aromatics. Waste disposal, risks of persistent pollutants, and the impact on aquatic life come up each year in safety reviews and compliance updates. Based on experience, using a compound with a clear profile—one that breaks down in a predictable fashion or can be destroyed efficiently—matters in long-term planning. Research teams weigh the environmental costs not just during synthesis but throughout a product’s lifecycle.
From industry reports and firsthand experience, fluorinated, brominated, and chlorinated aromatics have prompted lasting conversations in regulatory circles. Tracking fate in the environment, toxicity data, and breakdown products plays a growing role in determining which molecules make it from concept to commercial use. Companies and academic labs need to work with suppliers offering robust data on purity, batch testing, and support for environmental reporting. A lesser-known aspect is the growing practice of designing synthesis routes that minimize hazardous waste, a shift that often starts by picking intermediates with reliable, controlled reactivity.
Advances in synthetic methodology shine a spotlight on molecules like this one. Modern techniques make it possible to build complexity quickly, cutting down on waste and boosting efficiency. I’ve seen increased use of transition metal-catalyzed cross-couplings, where the bromine and chlorine atoms become key exchange points. Scientists say goodbye to laborious multistep pathways and instead use catalytic protocols to attach new fragments directly.
Fluorinated aromatics have gained traction in fluorine-19 MRI tracer development—here, careful substitution on the benzene ring controls not just chemical properties but imaging performance. The unique fingerprint of the fluorine atom broadens the scope for biologically relevant screening, an avenue impossible with plain nitrobenzenes or simple halogen substitutes. These advances become possible not because of new analytical tricks but because intermediates like 2-Fluoro-4-Bromo-5-Chloronitrobenzene bring needed flexibility to synthetic plans.
Even promising compounds come with hurdles. Drawing from the realities of day-to-day lab work, sourcing chemicals with unusual substitution can become expensive. Costs per gram may run higher compared to plain nitro- or halogenated benzenes. Groups with limited budgets or those working at early scales often share or recycle reagents, sometimes limiting the full scope of reactions they can tackle.
A practical solution: Investment from chemical suppliers in scaling up green synthesis routes. I’ve seen progress in catalytic fluorination and bromination, reducing both environmental footprint and cost. Developing robust purification at commercial scale—using chromatography-free isolation or crystallization—reduces solvent waste and makes prices more manageable for end-users. Suppliers who respond to calls for transparency on synthetic routes and commitment to greener chemistries set themselves up as preferred partners over those only interested in profit margins.
A second challenge lies in disposal and waste. Laboratories now track waste stream composition more closely, ensuring that halogenated byproducts are managed within permitted limits. A shift toward closed-loop manufacturing, with reclamation and reuse of solvents and halogenating agents, provides further environmental benefit. Researchers, too, need to report real-world use cases and unexpected reactivities to support a feedback cycle that keeps hazards in check.
Reflecting on nearly two decades of work in chemical research, I’ve learned to value molecules that offer something more than just another step in the synthesis checklist. 2-Fluoro-4-Bromo-5-Chloronitrobenzene shows how even specialized, less common intermediates provide outsized influence on progress in pharmaceuticals, materials science, and chemical biology. Sure, it won’t replace everyday workhorses like phenol or aniline in student labs, but for projects where failure rates climb and time matters, having such compounds in stock makes the difference between innovation and stagnation.
Teams running against deadlines or working to prove a new concept gain peace-of-mind from reliable intermediates with clear handling guidelines and consistent profiles. Their presence encourages exploration of new pathways—sometimes leading to better drugs, smarter devices, or deeper insights into molecular mechanics. By understanding the unique features of halogen and nitro placement, and committing to transparent, responsible sourcing and usage, researchers work not only toward scientific progress but also hold themselves accountable to environmental and ethical standards.
The chemistry community continues to evolve, balancing scientific curiosity, practical needs, and growing public scrutiny of chemicals’ impact on people and the planet. 2-Fluoro-4-Bromo-5-Chloronitrobenzene offers more than just a combination of atoms. It provides a gateway to advances in multiple industries, guided by thoughtful design, responsible sourcing, and an honest assessment of both value and risk. Experienced chemists—those who have worked through not just literature procedures but failed reactions, tough purifications, and scaled-up manufacturing—see value beyond the sum of its parts. As research pushes onward, molecules like this one will keep playing a quiet but essential role in shaping what’s next.