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HS Code |
548340 |
| Productname | 2-Bromo-3,4,5-Trifluoronitrobenzene |
| Casnumber | 328-78-9 |
| Molecularformula | C6HBrF3NO2 |
| Molecularweight | 256.97 |
| Appearance | Yellow to brown solid |
| Meltingpoint | 62-65°C |
| Density | 1.95 g/cm3 (estimated) |
| Purity | Typically ≥98% |
| Solubility | Slightly soluble in organic solvents |
| Smiles | C1=C(C(=C(C(=C1Br)F)F)[N+](=O)[O-])F |
| Inchi | InChI=1S/C6BrF3NO2/c7-3-1-4(8)6(11(12)13)5(9)2-3/8-5-4-3-7 |
| Storagetemperature | Store at 2-8°C |
| Hazardclass | Harmful if swallowed, causes skin irritation |
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2-Bromo-3,4,5-Trifluoronitrobenzene stands out as a fine example of how targeted functional groups can steer innovation in the chemical industry. As a substituted nitrobenzene carrying three fluorine atoms at the 3, 4, and 5 positions and a bromine at the second position, its molecular structure offers a rare blend of reactivity and selectivity. In the realm of advanced organic synthesis, the balance of electron-withdrawing effects and nucleophilic points has opened up new synthetic routes that traditional chloronitrobenzenes or less fluorinated options often struggle to provide.
The model of 2-Bromo-3,4,5-Trifluoronitrobenzene typically refers to its chemical formula, C6BrF3NO2, reflecting a compact aromatic ring studded with high-performance halogens and a nitro group. In experienced hands, each of these substituents means more than just a name on a structure map — they guide reactivity and downstream transformation. Drawing from time spent in synthesis labs and discussions with research colleagues, products like this often arrive as a crystalline solid, with purity levels routinely maintained above 97% thanks to chromatography and careful recrystallization.
This aromatic compound comes with a distinctive pale yellow color and shows melting points often landing between 65–75°C, an indicator that helps assess purity before committing to multi-step reactions. Solubility leans towards non-polar organic solvents such as dichloromethane or tetrahydrofuran, a trend shared by many halogenated aromatics. The low polarity preserves the reactivity of the nitro group and lets the bromine participate cleanly in cross-coupling reactions — qualities that lead scientists to pick this compound out of a crowded marketplace.
In laboratories and pilot-scale settings, the molecular profile of 2-Bromo-3,4,5-Trifluoronitrobenzene allows precise customization in making intermediates for pharmaceutical or agrochemical candidates. Contemporary research increasingly demands tight control over fluorine and bromine placement on the ring, given their influence over molecule metabolism, bioavailability, and environmental stability. In-person, I remember fellow chemists describing how subtle differences in fluorination pattern triggered changes in compound longevity or target protein engagement. This is no idle speculation — structural modifications have been central to the success of blockbuster drugs and robust crop protection agents alike.
Few compounds hold as much strategic value for medicinal and fine-chemical synthesis as this one. Its combination of a reactive bromine and electron-withdrawing trifluoronitro arrangement creates a two-pronged set of tools for building complexity. In the pharmaceutical sector, development pathways utilize the bromine atom’s reactivity in cross-coupling reactions. Suzuki, Stille, or Heck protocols absorb this compound into their workflows, leading to substituted biaryls, fluoroaromatics, or complex arene frameworks. In the last decade, use of tailored halogenated aromatic building blocks has soared as researchers chase new inhibitors or bioactive scaffolds with high metabolic stability.
Chemical engineers and process chemists appreciate how introducing three fluorine atoms optimizes certain target properties — from lipophilicity and metabolic resistance to membrane permeability. Each trait ties closely to actual patient outcomes or real-world product life cycles. Fluorinated aromatic rings slow phase I oxidation in living systems, extend half-life in plasma, and lend robust environmental profiles to specialty chemicals. It’s no accident that synthesis strategies favor this backbone for not just drug molecules, but for fluorinated materials and specialty dyes. Experience suggests that fluorine patterning, when combined with selective nitro activation, facilitates a one-stop precursor for a string of downstream modifications.
The nitro group brings a dual advantage. Its strong electron-withdrawing effect guides further substitution onto the arene ring, often at remote positions, handing synthetic designers leverage to install complexity in just a few steps. Even in my own experimentation, swapping out nitro for amine or carrying it through to reductive transformations opens a window to value-added intermediates. Especially in the scale-up context, chemists report that a well-positioned nitro group spares both time and cost for downstream reduction or functionalization.
Distilling the practical advantages of 2-Bromo-3,4,5-Trifluoronitrobenzene means contrasting it with related options like mono-fluorinated or di-fluorinated analogues, and standard bromonitrobenzenes lacking full trifluoro substitution. From direct feedback in medicinal chemistry and agrochemical R&D, the key difference centers on the unique substitution pattern that helps mediate both activity and process simplicity.
Broader halogenation — particularly with a triad of fluorines — injects a suite of physical and chemical resilience into the backbone. The 3, 4, 5-trifluoro substitution pattern brings a symmetry that distributes electron density and stabilizes the aromatic ring, influencing both how the molecule reacts under standard laboratory conditions and how it resists degradation in biological environments. Competing products usually deliver only partial fluoro coverage, which leads to less predictable reactivity and sometimes a weaker overall effect on the pharmacological or physical profile of resulting products.
The bromine atom at the ortho position, as found in this molecule, enables highly selective cross-coupling. Compared to alternatives bearing a chlorine or iodine atom, bromine strikes a compromise between reactivity and economic cost. In direct experimentation, many chemists have found that aryl bromides lead to cleaner coupling products under milder conditions, while iodides often drift toward instability or excess reactivity, and chlorides can resist activation unless pushed hard. In process optimization meetings, the potential reduction in catalyst load and higher purity of coupling partners often wins over purchasing departments facing tight timelines.
Compared with isomeric forms bearing another arrangement of fluorine or nitro placement, 2-Bromo-3,4,5-Trifluoronitrobenzene consistently comes up as a favorite for multi-step synthesis planning. This is not just a theoretical decision — in practical research settings, yields and product purities routinely beat out less fluorinated or differently arranged competitors, cutting down on costly purification steps and minimizing material loss. Experienced chemists also highlight that the assembly using this scaffold reduces side reactions common in more activated or electron-rich nitrobenzenes.
Across research and scale-up environments, users of 2-Bromo-3,4,5-Trifluoronitrobenzene rely on the lessons shared person-to-person. Unlike more exotic or highly activated intermediates, this compound rarely brings unexpected reactivity or runaway byproducts when handled with standard good laboratory practice. Its moderate melting point and crystalline texture make for reliable weighing and transfer, and the pale yellow hue provides a visible cue during manipulations.
The blend of bromine and nitro functionality, though potent, remains manageable with routine safety precautions, especially in comparison to highly electrophilic nitrosoaromatics or polynitrobenzenes. Still, the standard caution around inhalation, dust formation, and glove permeability always applies. Many learn early to store such halogenated compounds in tightly sealed containers away from direct sunlight, and to avoid strong bases that could unmask reactivity.
The broader community of synthetic chemists pays special attention to waste streams, since both brominated and fluorinated aromatic compounds can pose environmental challenges if released. At the bench and in pilot plants, working with partners on safer degradation or incineration options for residual material forms part of every procedural rundown. This responsible approach aligns with growing regulatory focus on halogenated intermediates, and thoughtful suppliers increasingly provide technical support for compliant handling and disposal.
Choosing reagents with high molecular efficiency and low byproduct formation, as with this one, also fits with green chemistry goals. In more than a few group meetings, the sustainable synthesis angle has made the difference when project teams weighed procurement choices, nudging adoption of reagents with a smaller environmental and waste footprint while still offering high synthetic reliability.
After seeing the chemistry in action on pharmaceutical development projects, the strengths of 2-Bromo-3,4,5-Trifluoronitrobenzene rarely remain theoretical. Discussions with industry colleagues point to successful incorporation in several areas — from scaffolds in oncology and antiviral research to agricultural products aiming at pest resistance and environmental stability. While the specifics of drug pipelines remain confidential, the recurring mention of halogenated aromatic building blocks testifies to their foundational role in target-driven molecule assembly.
Researchers working in materials science and functional coatings also look to this scaffold for its ability to serve as a precursor to advanced fluorinated polymers and surface modifiers. Fluorinated nitrobenzenes impart hydrophobicity and tune dielectric properties, a feature in demand for high-performance coatings, flexible electronics, or specialty adhesives. Projects exploring membrane materials or optoelectronic components benefit from the predictable substitution reactions enabled by the bromine and nitro groups.
Academic settings do not get left out. Graduate students and trainee chemists have cited success with coupling reactions using this compound as a teaching tool, given its relative accessibility and robust outcome in Suzuki and Buchwald-Hartwig protocols. The ability to illustrate advanced functional group interplays draws in future practitioners, reinforcing the molecular logic behind modern synthesis planning.
Market statistics and patent trends both show rising demand for heavily fluorinated aromatic intermediates in crop protection and life sciences. The underlying driver lies in the mounting need for molecules that withstand UV degradation, microbial attack, and harsh field conditions. The same trifluorination that sets this compound apart also imparts durability to end products. Reports from agrochemical developers praise the stability, while feedback from process scale-ups indicates that production runs enjoy lower batch-to-batch variability as a result.
Biologists have observed that increased fluorine content shifts not only the chemical destiny of agrochemicals but also their interaction with target organisms. The pattern of ring substitution uniquely delays enzymatic attack, granting extended action windows for actives derived from this intermediate. Lives and livelihoods often depend on that extra week or month of protection. The message from those on the frontlines of agricultural biotechnology remains straightforward — investment in robust chemical backbones pays dividends in field results and regulatory approvals.
Disposal and long-term stability in soils remain critical topics. The industry trend toward detailed environmental impact assessment and transparency means intermediates chosen today need a strong safety record. Over the past decade, the fluorinated aromatic class has steadily gained acceptance thanks to favorable data on degradation pathways and a comparatively low propensity for persistent organic pollutant formation. While no chemical is truly inert in the environment, advances in remediation and containment make use of functionalized nitrobenzenes a calculated and sensible decision.
Part of what makes 2-Bromo-3,4,5-Trifluoronitrobenzene a fixture in advanced synthesis stems from quality of supply. Stories circulate about failed batches, but those who partner with suppliers skilled in organofluorine chemistry and sophisticated purification take less risk. Experienced technical teams leverage a combination of NMR, HPLC, and mass spectral methods to document purity and support traceability all along the production chain.
The value of technical documentation and transparent batch records grows every year. In regulated sectors like pharmaceuticals, even a minor slip in purity or contaminant profile can derail months or years of work. Chemical buyers now seek not only product but expertise — letters of analysis, formulation advice, and support for regulatory audits. Engaged suppliers walk through both synthetic options and potential troubleshooting before issues arise, easing pressure on research and development teams.
What I have found from my own experience echo this pattern: projects that blend strong technical consulting with proven raw material supplies weather the pressures of innovation better than those focused solely on chasing the lowest cost. In an era of tight margins and fast progress, this steady hand on the synthetic wheel makes a difference from discovery labs to the scale-up floor.
Looking at recent literature and patents, innovation with heavily substituted nitrobenzenes points toward more sustainable, selective, and high-yielding transformations. Late-stage fluorination and tailored cross-coupling now dominate the strategies of both established companies and new entrants. For the bench chemist, this means the days of brute-force aromatic substitutions are fading; usability, functional outcome, and cost all matter more.
In many R&D circles, efforts center on pushing the limits of what these intermediates can do — combining them with emerging catalysts, non-traditional solvents, and continuous process technologies. Hands-on experimentation — the cycle of trial, analysis, learning, and iteration — marks the leading groups in this space. Those who spend time optimizing around 2-Bromo-3,4,5-Trifluoronitrobenzene often end up with more options for further molecular building, greater control over stereochemistry, and reduction in waste streams.
The interplay between structure and activity continues to drive pharmaceutical pipelines, posing new puzzles and opportunities. In every instance, the ability to deploy a well-defined intermediate cuts both cost and complexity — a lesson reinforced across project retrospectives and post-mortems. The take-home message from innovators is clear: success favors not only the bold but the prepared, especially those willing to build advantage at the molecular foundation of their programs.
Every year, the demand for documented safety and sustainability increases. Traditional materials can no longer coast on historic use alone. Halogenated aromatic intermediates, for all their utility, attract scrutiny because of potential legacy environmental issues. Maintaining compliance means active adaptation at every step, from product sourcing through end-of-life management. Many practitioners view the choice of intermediate as an inflection point — set the right tone here, and the rest of the pathway unfolds with fewer surprises.
Product stewardship programs now include detailed lifecycle assessments, release and fate modeling, and community engagement. These are not afterthoughts. Thoughtful chemical producers and purchasers use the data and insight to shape both material selection and production planning. In this environment, a compound like 2-Bromo-3,4,5-Trifluoronitrobenzene, with a robust track record and clear documentation, commands respect for its reliability and manageable risk profile.
The story of 2-Bromo-3,4,5-Trifluoronitrobenzene, while grounded in chemistry, echoes a broader theme running through material science, pharmaceuticals, and agrochemistry: choosing the right building block pays off at every stage. Time and again, efforts to cut corners early only compound challenges downstream. Hands-on experience and the testimony of colleagues across sectors suggest a simple truth — investing in reliable, versatile, and well-characterized intermediates grants creative latitude for breakthroughs and protects against costly error.
The next wave of innovation will likely bring novel transformations, heterocyclic expansions, and digital process control further into the synthesis suite. As regulatory and environmental hurdles climb, more value will accrue to intermediates proven to weather scrutiny. This compound’s blend of reactivity, stability, and accessibility sets it up as a mainstay of advanced organic synthesis for years to come, cementing its place in the growing toolkit of any chemist facing the challenge of modern molecular assembly.
Drawing from years of direct laboratory engagement, supplier collaboration, and hard-won project experience, it becomes clear why 2-Bromo-3,4,5-Trifluoronitrobenzene attracts attention and sustained adoption across high-value sectors. Practical, reliable, and richly endowed with the molecular features demanded by advanced synthesis, it answers a spectrum of technical and strategic needs. The ongoing exchange of knowledge among researchers further magnifies its value, ensuring that each new project stands not only on the shoulders of chemistry, but also on the practical lessons of those who have shaped the field over decades.