|
HS Code |
750467 |
| Chemical Name | 3-Bromo-4-Chlorobenzoic Acid |
| Molecular Formula | C7H4BrClO2 |
| Molecular Weight | 235.46 g/mol |
| Cas Number | 21739-92-4 |
| Appearance | White to off-white solid |
| Melting Point | 181-184°C |
| Solubility In Water | Slightly soluble |
| Density | 1.79 g/cm³ (calculated) |
| Purity | Typically ≥98% |
| Smiles | C1=CC(=C(C=C1C(=O)O)Br)Cl |
| Inchi | InChI=1S/C7H4BrClO2/c8-5-3-4(7(10)11)1-2-6(5)9/h1-3H,(H,10,11) |
| Synonyms | 3-Bromo-4-chlorobenzoic acid |
| Pka | 3.9 (approximate, for carboxylic acid group) |
| Storage Conditions | Store at room temperature, tightly closed, dry place |
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In my years studying and working in chemical research, I’ve run across a wide range of compounds—some forgettable, some indispensable. Among the countless benzoic acid derivatives, 3-Bromo-4-Chlorobenzoic Acid stands out as a workhorse in the lab, particularly in medicinal, agrochemical, and material science settings. Every bottle you’ll find on the shelf has a story that traces back to decades of organic synthesis and growing industrial needs. There’s a reason this compound finds such steady demand, and it’s worth unpacking how it functions, where it excels, and how it differs from similar chemicals.
This compound goes by its name for good reason—its structure boasts a bromine atom on the third carbon and a chlorine atom on the fourth carbon of the benzoic acid ring. At a molecular level, that combination brings both reactivity and selectivity to synthetic chemistry. The acid group anchors the molecule and lets it participate in reactions where chemists want to graft other functional groups, build new rings, or set up more complex transformations.
In the world of custom synthesis, small changes to a molecule—something like swapping out a hydrogen for a chlorine or bromine—can have huge effects on how it behaves. By including both bulky bromine and electron-withdrawing chlorine atoms, this particular compound controls reaction rates and outcomes in ways you can’t always predict, even after years of experience. That keeps things interesting, but it also means chemists reach for this acid when their trusted benzoic acids hit a dead end.
Anytime I sit down with a new synthesis project, early questions always revolve around which building blocks lend the most versatility. 3-Bromo-4-Chlorobenzoic Acid often winds up as an integral player for a few reasons. It can act as a handy precursor for more advanced molecules. The acid group usually gets transformed—either into esters, amides, or more complicated chains. The presence of both chlorine and bromine atoms on the aromatic ring lets chemists leverage various coupling reactions, such as Suzuki and Buchwald–Hartwig couplings, which many modern drug and material discoveries depend on.
Pharmaceutical research, for instance, values structure-activity relationship (SAR) studies, where scientists tweak a molecule’s pieces to see how small modifications affect biological activity. With both halogen atoms, 3-Bromo-4-Chlorobenzoic Acid allows for nuanced changes to the electronic and steric environment, helping researchers find the sweet spot between activity and safety for potential drugs. The same logic holds true in crop science—muted reactivity in one derivative can mean the difference between an effective plant regulator and a product too toxic for market.
On the material science side, researchers incorporate this acid into specialty polymers and advanced coatings. Properties like hydrophobicity, electrical characteristics, and resistance to environmental degradation stem from its unique combination of atoms. Additions such as bromine often introduce flame retardancy, while chlorine can influence mechanical properties. Both substitutions make this compound valuable in plastics, insulating materials, and even certain electronics applications that demand fine-tuned performance.
If you look up benzoic acid derivatives, the shelves aren’t bare. A glance will show compounds like 2-Chlorobenzoic Acid, 4-Bromobenzoic Acid, or dichloro- and dibromo analogs. Each has its fans. The balance of reactivity and control changes depending on where those halogen atoms attach to the ring and which ones you pick.
Take 2-Chlorobenzoic Acid, for example. Chlorine’s impact on the ring, especially in the ortho position, pushes reactions toward certain pathways, sometimes favoring rearrangements or other side reactions. 3-Bromo-4-Chlorobenzoic Acid, with its halogen atoms separated by a carbon, lets you tap into both electron-withdrawing and steric effects, giving synthetic chemists more levers to pull when mapping a reaction route. That spacing between bromine and chlorine means fewer surprises and greater control—asset in complex multi-step syntheses.
Many chemists gravitate toward the classic 4-Bromobenzoic Acid for cross-coupling work. It shines in some reactions and stumbles in others, especially where the extra chlorine atom would further tweak reactivity or electronic characteristics in valuable ways. The dual-halogen design in the 3-Bromo-4-Chloro derivative creates more opportunities to access otherwise tricky compounds. The difference isn’t just on paper—it turns up in reaction yields, purity, and timescales that make or break a production run.
Dibromo or dichloro analogs offer even more impressive electron withdrawal and sometimes prove too unreactive or too bulky for applications in pharmaceuticals or fine chemicals. Here, the 3-Bromo-4-Chloro version lands in a Goldilocks zone: giving enough reactivity and steric shielding without closing off synthetic options.
Most of what matters in the lab comes down to purity and storage stability. Chemists typically source 3-Bromo-4-Chlorobenzoic Acid at purities of 98 percent or higher, which is more than adequate for nearly every application outside of analytical reference standards. Its solid state at room temperature means trouble-free weighing, minimal dust, and a shelf life that doesn’t challenge routine storage if kept dry and out of direct light. Its melting point, typically in the 195–200°C range, also helps with identifying and confirming the sample, especially during crude purity checks.
Its moderate solubility in organic solvents such as dichloromethane and ethyl acetate means formulating stock solutions is straightforward and predictable. In my own runs, solutions of 3-Bromo-4-Chlorobenzoic Acid have rarely shown the extremes of stickiness, oiling out, or hygroscopic behavior sometimes seen in more polar or highly functionalized aromatics. This stability streamlines handling and reduces headaches for both small-scale research and larger batch manufacturing.
One thing that strikes anyone who’s spent time preparing and transforming benzoic acid derivatives is how sensitive some reactions are to even minor impurities. Trace amounts of water, low-level metal contamination, or minor isomeric differences can lead to serious drops in yield and selectivity. High-purity 3-Bromo-4-Chlorobenzoic Acid consistently performs as advertised—no excess tars, unwanted crystallization, or unpredictable decompositions, provided good lab practices stay in place.
Batch consistency translates straight into confidence for anyone running time-consuming or costly reactions. Consistency avoids costly reruns and means fewer unpleasant surprises downstream, such as stubborn byproducts that gum up purification columns or taint spectral data. I’ve seen groups waste days chasing purity only to find the trouble traced back to questionable starting materials. 3-Bromo-4-Chlorobenzoic Acid’s reputation for quality and shelf life makes it a go-to starting point when stakes are high.
From a practical angle, the global chemical supply chain rarely gets headlines unless something goes wrong. Raw material security and cost curves determine what compounds make it into regular catalogs. 3-Bromo-4-Chlorobenzoic Acid benefits from well-developed upstream supply routes for brominating and chlorinating benzoic acid. Prices have stabilized over the years due to solid demand in contract research, generics, and specialty chemicals. While sudden spikes in halogen feedstock prices or regulatory hurdles can cause short-term bumps, the widespread formulation expertise across North America, Europe, and Asia provides a buffer against outright shortages.
Unlike niche building blocks that only see daylight in boutique syntheses, this acid enjoys high enough industrial throughput to support labs at scale without straining global inventories. In my own purchasing, long-term contracts and relationships with reliable suppliers prevent sudden bottlenecks, letting projects proceed without delay—a margin of security that benefits research labs as well as commercial ventures.
Anytime you deal with halogenated compounds, there’s a reminder that chemical convenience comes with waste and safety considerations. Some colleagues get jumpy around everything with chlorine or bromine, aided by horror stories of environmental contamination. Treatment and disposal call for strict adherence to protocols; halogenated waste streams must follow proper incineration or reclamation routes. Luckily, 3-Bromo-4-Chlorobenzoic Acid itself is a stable solid—it doesn’t easily volatilize or leak, unlike lighter, more volatile analogs, so handling it in a fume hood using gloves and goggles suits most scenarios.
On the research end, published toxicological data on closely related compounds guides risk assessment. Acute toxicity sits at levels requiring respect but not alarm when proper precautions guide bench work. Most incidents stem from careless spills or failures to dispose of solutions appropriately. In industry, tracking usage and exposure ensures compliance with workplace health standards and keeps teams safe. There’s always a push to more sustainable chemistry, and research into greener synthesis routes for halogenated aromatics grows every year.
Half the value of 3-Bromo-4-Chlorobenzoic Acid comes not from what it is, but the scientific obstacles it helps circumvent. In packed workdays spent troubleshooting failed couplings or screening reaction conditions, having reliable starting materials compounds success. Some molecules have gained notoriety for persistent side reactions, dropped yields, or runaway polymerization. This acid sidesteps many such traps—its balance of steric bulk and electron withdrawal facilitates clean couplings and substitutions.
I’ve found that with small adjustments to temperature or catalyst loadings, most reactions involving 3-Bromo-4-Chlorobenzoic Acid produce benchmarks for optimization. Its predictable reactivity enables thorough exploration of synthetic space without walking into dead ends. That saves time, reduces waste, and improves reproducibility—an asset for multi-step syntheses where each stage must deliver for the whole to succeed.
That said, the same electronic and steric features that provide control also mean certain transformations require powerful catalysts or conditions. For example, some nucleophilic substitutions or reductions demand higher temperatures or specialized solvents. Solutions rely on modern cross-coupling technology and ligand design, both of which continue to advance thanks to feedback from large numbers of synthetic trials involving this compound.
Every so often, a molecule’s value becomes evident from breakthroughs far removed from the original lab work. In my experience, pharmaceutical lead development, polymer material improvements, and agrochemical advances frequently trace back to the clever use of halogenated aromatics. 3-Bromo-4-Chlorobenzoic Acid allows for late-stage diversification in drug discovery; a biologist or chemist can modify leads by swapping out the acid or one of its substituents. Such flexibility can mean the difference between project shelved and drug approved.
In advanced polymers, research teams have explored derivatives of this compound to impart fire resistance or modify crystallinity. It isn’t just about making something with better durability—improvements often appear in electrical insulation or resistance to UV degradation. Success stories sometimes filter down to automotive or aerospace materials, which rely on incremental innovation at the chemistry level to deliver safer and longer-lasting products.
Many researchers enjoy the purity and ease of lab-scale work, only to hit snags scaling to pilot or industrial capacity. Large-scale synthesis of 3-Bromo-4-Chlorobenzoic Acid follows established protocols, aided by robust literature and accumulated process experience. Key process controls—temperature, rate of halogen addition, continuous monitoring—keep contaminant levels in check and minimize by-product formation.
From my perspective, scaling chemical processes calls for more than just larger vessels and better stirrers. It demands an understanding of thermal management, reaction kinetics, and purification strategies. Here, the chemical stability and solid-state form of this acid ease the hurdles that cause delays or added costs for more delicate or unstable intermediates. Supply continuity depends on batch reproducibility and the clean crystallization of the product, both strong suits for this compound.
No product escapes limitations. I’ve seen attempts to force-fit 3-Bromo-4-Chlorobenzoic Acid into synthetic pathways where milder or less hindered acids might outperform it. Bulky substituents can sometimes impede multi-coupling strategies or limit solubility in specialized solvents. There’s still a need for ongoing process innovation: greener synthesis, reduced halogen usage, better catalyst recycling, and recovery of by-products for reuse.
Collaborative research between academia and industry stands out as an effective way to drive progress. New catalytic systems, microwave-assisted processes, and flow chemistry promise higher yields with less environmental impact. Instead of discarding old chemistries, adding new technology and process controls unlocks the further utility of established building blocks like this acid, benefiting workflow and sustainability.
What’s often left unsaid in technical sheets is the role of collective experience—the silent understanding among chemists of what works and what avoids headaches. Talk to a handful of researchers, and the verdict on 3-Bromo-4-Chlorobenzoic Acid is almost always positive. Reliability, clean reactions, and clear analytical profiles pop up in these conversations. Broader adoption in patent filings and published research continues to build a track record that new users can trust.
Feedback loops matter. Published failures, shared troubleshooting, and community forums reduce time lost to repeated errors. Over the years, improvements in process safety, yield, and disposal protocols for compounds like this haven’t come from corporate memos but from the pilot plants and fume hoods where theory meets reality. This spirit of open dialogue and trial-and-error improvement has shaped not just the perception but the actual quality and utility of 3-Bromo-4-Chlorobenzoic Acid.
The conversation is shifting in laboratories worldwide—from the singular focus on yield and purity to a more comprehensive view of lifecycle impact and green chemistry. Sustainable routes to halogenated aromatics, powered by renewable feedstocks or lower-energy processes, are no longer pipe dreams. I’ve seen real progress in pilot-scale substitution methods that cut down toxic by-products or curb the use of hazardous reagents.
The continued relevance of 3-Bromo-4-Chlorobenzoic Acid in the next generation of research and production will hinge on its adaptability to greener, safer processes. Chemical companies already look to close the loop on halogen use, recycling spent reactants and slashing emissions. Researchers in academia and industry alike recognize that the most enduring building blocks are the ones that fit within emerging regulatory and ethical frameworks. The compound has the right balance of utility and adaptability to meet these challenges, provided ongoing vigilance shapes its manufacture and use.
With all the talk of innovation and disruption, some of the most valuable advances rely on solid, well-understood chemistry. 3-Bromo-4-Chlorobenzoic Acid serves as a textbook case—a compound with deep roots and wide branches. Its blend of reactivity, stability, and versatility has made it a linchpin in drug discovery, advanced materials, and more. Continued utility comes from adoption of updated practices that respect both the past and future of chemical manufacturing. Direct, honest sharing of results, both good and bad, will ensure the next generation inherits the best version of this indispensable research tool.