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HS Code |
714583 |
| Compound Name | Β-(3-Bromo-5-Chlorophenyl)Boronic Acid |
| Chemical Formula | C6H5BBrClO2 |
| Cas Number | 870299-39-7 |
| Appearance | White to off-white solid |
| Solubility | Slightly soluble in water, soluble in organic solvents |
| Purity | Typically ≥97% |
| Storage Conditions | Store at 2-8°C, protected from moisture |
| Smiles | B(C1=CC(Br)=CC(Cl)=C1)(O)O |
| Inchi | InChI=1S/C6H5BBrClO2/c8-4-1-5(7(10)11)3-6(9)2-4/h1-3,10-11H |
| Applications | Used as a building block in Suzuki coupling and organic synthesis |
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Boron-based compounds have changed the landscape of organic chemistry in recent years, especially for researchers chasing new pharmaceutical leads and advanced materials. As someone who’s spent quite a few late nights working on cross-coupling reactions, I've developed a deep respect for the precision that specialized reagents can offer. Among the new players making an impact, Β-(3-Bromo-5-Chlorophenyl)Boronic Acid stands out not just because it features both bromine and chlorine on a single aryl ring but because its profile fits so many reaction schemes that would leave less robust boronic acids sidelined.
Β-(3-Bromo-5-Chlorophenyl)Boronic Acid carries a molecular formula that’s compact but loaded with possibilities. Its core skeleton, defined by the phenyl ring with bromine at the 3-position and chlorine at the 5-position, creates a target for Suzuki-Miyaura coupling reactions. These couplings make up the backbone of constructing new carbon-carbon bonds, especially in the pharmaceutical world. The added benefit with β-(3-Bromo-5-Chlorophenyl)Boronic Acid comes from the unique push and pull between the two halogens. This combination opens doors to selectivity when it comes to further functionalizations, which is not something every phenylboronic acid offers.
In the context of drug discovery, reactions have to work the first time and with high yield. I remember an early project that brought up the problem of selectivity in late-stage functionalization. By using a boronic acid with both bromine and chlorine substituents, we fine-tuned reactivity to direct subsequent transformations more precisely. Β-(3-Bromo-5-Chlorophenyl)Boronic Acid allowed for robust coupling without scrambling the rest of the molecule. Its stability over a reasonable range of pH and its relative tolerance to water contamination give it an edge over less stable boronic acids. This isn’t merely a time-saver — it means fewer purification headaches, which any chemist will say makes the workday a lot smoother.
Many boronic acid derivatives suffer from issues with solubility or decompose under mild basic conditions. I’ve worked with analogues that seemed fine on paper but fizzled out under scale-up, either hydrolyzing too fast or simply refusing to dissolve at working concentrations. Β-(3-Bromo-5-Chlorophenyl)Boronic Acid carries both bromine and chlorine, which changes electron density on the ring and can improve shelf-life, sometimes by months compared to unsubstituted phenylboronic acids. In Suzuki couplings, this often makes the difference between a robust, reliable method and a barely repeatable one.
Every step in a chemical synthesis needs to earn its place. Lab teams often hunt for reactions that can run at room temperature, cut out expensive catalysts, or withstand minor lapses in technique. Β-(3-Bromo-5-Chlorophenyl)Boronic Acid brings enough stability to run in standard laboratory glassware and with most typical solvents. In my experience, it resists the kind of overreaction that leads to messy side products. The comparative ease of isolation after reaction reduces time spent at the chromatography column. Not every boronic acid can claim this; some force you to spend hours with silica gel or struggle with poor solubility during workup.
The pharmaceutical industry moves quickly, with high-throughput screening methods and demands for faster development timelines. Β-(3-Bromo-5-Chlorophenyl)Boronic Acid suits these needs because it allows for modular synthesis — tweaking one functional group at a time to refine activity and minimize side effects. In materials science, the need for robust cross-coupling partners extends beyond drugs. Creating new organic semiconductors or advanced polymers often relies on the availability of niche boronic acids. Here, the acid’s dual-halide identity simplifies the creation of molecules with built-in handles for post-synthetic modification, or for tuning electron flow across the backbone of a device.
Routine phenylboronic acid works well for basic cross-couplings, but chemists regularly run into problems with selectivity. Sometimes you want to incorporate a second functional group, but unprotected boronic acids will decompose under certain conditions, or the reaction simply doesn’t go far enough. Through bench experience, I've learned the advantage of using boronic acids with one or more halide substituents. The bromine and chlorine on β-(3-Bromo-5-Chlorophenyl)Boronic Acid don’t just tweak electronics; they actively shape which other atoms you can swap in — like when you want to introduce a heterocycle or an alkyl group specifically at the 3- or 5- position relative to the boronic acid. The presence of two different halogens also encourages stepwise functionalization, letting me tack on two different groups one after the other, basically constructing unique scaffolds that would have been much harder to achieve with more generic reagents.
Looking at products offered by leading chemical suppliers, beta-(3-Bromo-5-Chlorophenyl)Boronic Acid is available in purities typically above 97%. Lab-grade material should come as a crystalline solid, which keeps measuring and weighing straightforward, and storage under standard dry-room conditions avoids degradation. Packaging in amber glass bottles protects against light, reducing the chance of unwanted side reactions. Consistent material quality between lots is essential, especially in regulated industries like pharma. In my labs, we test the material via NMR and HPLC to ensure it matches catalog data; inconsistency wreaks havoc on scale-up, and β-(3-Bromo-5-Chlorophenyl)Boronic Acid has demonstrated tight spec adherence when sourced from reputable vendors. This reliability gives project managers confidence to push projects into pilot batches faster.
Boronic acids, including β-(3-Bromo-5-Chlorophenyl)Boronic Acid, generally warrant standard chemical precautions: gloves, goggles, fume hoods, and careful shelf placement. A few years back, I had a spill with a generic boronic acid. Luckily, the solid form here minimizes dust and handles more easily — less chance for airborne exposure. Environmental impact always stays top of mind, and while most aryl boronic acids are not especially hazardous, proper disposal is still important. Waste streams containing boron compounds go for specialized incineration or chemical neutralization, preventing trace contamination of water supplies. Teams working with this class of chemicals find that handling protocols written for phenylboronic acid often translate directly to β-(3-Bromo-5-Chlorophenyl)Boronic Acid, streamlining both lab safety and regulatory compliance.
Academic groups and commercial labs want reliability on both quality and supply. Based on my time corresponding with purchasing departments, delay in key intermediates can derail a development schedule for months. β-(3-Bromo-5-Chlorophenyl)Boronic Acid enjoys broad catalog coverage, supported by major chemical suppliers operating internationally. Shippers provide robust data sheets, lot traceability, and real-time support — all features in demand by regulatory-conscious corporations. Labs in North America, Europe, and parts of Asia often receive product within days. For operations in more remote areas, air-shipped solid weighs less and arrives in better shape compared to more sensitive boronic ester analogues, which can hydrolyze in humid transit.
I’ve spent many hours scouting new ligands and catalysts, testing how different boronic acids behave in real-world Suzuki couplings. The solubility and reactivity tweaks from dual-halide substitution make β-(3-Bromo-5-Chlorophenyl)Boronic Acid a logical first pick for reactions targeting electron-deficient or sterically-hindered aryl targets. As a researcher, I appreciated not worrying about premature hydrolysis or byproducts from boroxine formation, which often complicate purification steps. I recall one specific series of couplings involving nitrogen-rich heterocycles, a substrate class that often binds up palladium and stalls the whole process. The boronic acid’s halide-induced electron-withdrawing effects supported much smoother reactions, delivering higher isolated yields and cleaner reaction profiles on both small and multi-gram scales.
Selectivity challenges come up daily in chemical research. The presence of both bromine and chlorine means I can leverage orthogonal reactivities: substituting additional groups after the Suzuki coupling often calls for different reagents, sometimes copper-mediated for chlorine, sometimes using palladium for bromine. This orthogonality supports sequential reactions, a trick often used in medicinal chemistry to build complexity while retaining control over atom placement. I’ve witnessed teams take advantage of such sequential couplings to synthesize lead compounds with one structural motif at the 3-position and another at the 5-position, all without harsh deprotection steps or complicated workarounds.
One persistent issue I hear about in supplier meetings is the limited number of vendors offering kilogram quantities with proper certification and documentation. For industrial users scaling up from grams to kilos, the cost and consistency must stay in check. This trend isn’t unique, but it feels more pronounced as regulatory requirements increase each year. Developing greener synthesis routes to β-(3-Bromo-5-Chlorophenyl)Boronic Acid would help, both in lowering byproduct formation and energy use. Some research teams have looked at direct borylation methods that avoid hazardous intermediates, making production less polluting, while improved purification methods — like real-time crystallization monitoring — cut down on process waste. Better logistics management and real-time supply tracking, backed by digital inventory platforms, will further lessen work interruptions and inventory shortages in busy labs worldwide. These process improvements are the sort of changes that actually flow down to faster drug and device development timelines, benefitting end-users as much as the scientists handling the raw materials.
Having spent years in multi-disciplinary chemical research, I’ve come to appreciate how a single reagent, correctly chosen, can streamline project flow and cut down on troubleshooting. Β-(3-Bromo-5-Chlorophenyl)Boronic Acid shines not because it redefines what’s possible, but because it quietly expands the working toolkit of scientists across pharma and materials labs. It delivers performance reliability, gives options when selectivity is in play, and meets the real, day-to-day demands of chemical synthesis. For scientists who juggle limited time and tight budgets, tools like this compound aren’t luxury items, but essential partners in the search for new medicines and breakthrough materials.