|
HS Code |
289184 |
| Iupac Name | 3-Bromo-2-hydroxybenzoic acid |
| Molecular Formula | C7H5BrO3 |
| Molecular Weight | 217.02 g/mol |
| Cas Number | 5589-46-0 |
| Appearance | White to pale yellow crystalline powder |
| Melting Point | 195-199°C |
| Solubility In Water | Slightly soluble |
| Density | 1.89 g/cm³ (approximate) |
| Pka | 2.9 (carboxylic acid group) |
| Smiles | C1=CC(=C(C(=C1Br)O)C(=O)O) |
| Pubchem Cid | 13436 |
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Sometimes, the most important gains in research and industry come from the thoughtful use of materials that rarely catch headlines. 3-Bromo-2-hydroxybenzoic acid lands firmly in this camp. Chemists, material scientists, and pharmaceutical teams look for compounds like this one not for their popularity but for the quiet versatility and reliability they bring into the workflow.
Think about benzoic acid derivatives and their impact on organic synthesis—3-Bromo-2-hydroxybenzoic acid stands out due to its substitution pattern, which places bromine at the third position and a hydroxyl group next to the carboxylic end. This simple adjustment changes everything. The molecular formula tells part of its story: C7H5BrO3, a structure that puts both reactivity and selectivity into the chemist’s hands. It has a white to off-white appearance and delivers reliable stability in standard laboratory conditions. Much of its value stems from accessibility—both in physical handling and in how the molecule interacts during synthesis.
My own work in an organic laboratory put this compound on my radar during the hunt for new ways to create substituted salicylic acids. The bromine atom opens doors for cross-coupling reactions, while the phenolic hydroxyl group allows further functional tweaks. If you’ve ever puzzled over optimizing a reaction for yield without opening a can of worms, discovering a compound with this kind of dual handle feels like a small breakthrough.
Researchers often turn to 3-Bromo-2-hydroxybenzoic acid for routes that demand both activation and selectivity. When dealing with halogenated aromatics, the bromine works as a useful point of attachment for Suzuki or Heck reactions. In practice, this leads to new biaryl compounds or tailored pharmaceutical intermediates. The hydroxyl group doesn’t get overshadowed—it sticks around to help form esters, ethers, or other protective groups, making downstream steps more manageable. Every chemist knows the headache of rearrangements or side-reactions. Here, the structure reduces unwanted detours thanks to the electronic effects of the substituents, which streamline reactivity.
From a practical perspective, its slightly higher molecular weight, compared to unsubstituted salicylic acid, means purification can proceed more smoothly following standard procedures like recrystallization or column chromatography. Its solubility in common organic solvents—think acetone, DCM, and ethanol—makes room for flexible work-ups. This accounts for some of the repeat use it sees across diverse laboratory projects.
In a chemical marketplace crowded with substituted benzoic acids, it helps to cut through the noise by examining what sets this compound apart. Regular 2-hydroxybenzoic acid, also known as salicylic acid, has broad applications but falls short when a halogen’s reactive edge is needed. On the other hand, 3-bromobenzoic acid presents strong halogenation, yet loses out on the extra nucleophilicity and hydrogen-bonding potential that comes from the hydroxyl group. The unique pairing in 3-Bromo-2-hydroxybenzoic acid strikes a rare balance—you get tunable reactivity plus selective derivatization.
Time and again, I’ve witnessed graduate students stuck at a crossroads, debating which functional group to introduce or protect first. This compound simplifies those choices. Additions, substitutions, and condensations often run more straightforwardly, since the electronic interplay between the bromine and the hydroxyl group crafts an environment ripe for directed reactions. This means easier method development, smaller budgets spent on optimization, and more dependable access to rare intermediates needed for research pipelines.
Moving away from theory for a second, the real-world demand for high-purity active pharmaceutical ingredients and advanced materials keeps tweaking the preferred reagents list. 3-Bromo-2-hydroxybenzoic acid consistently lands on that list for teams working on kinase inhibitors, dye precursors, or even agrochemical actives. Its chemical fingerprint allows for finer control over the resulting molecules, making it a tested ally in custom synthesis.
Supply always matters in chemistry, not just from a logistical standpoint but from a confidence one. The best suppliers ensure that batches of 3-Bromo-2-hydroxybenzoic acid meet high standards for purity, typically exceeding 98%, and land well within expected melting ranges, which hovers around 194-198°C. Most working chemists appreciate that a consistent melting point quickly weeds out off-spec material. If a sample shows a wide or depressed melting range, I’d set it aside—experience teaches that many headaches trace back to poor material quality.
Spectroscopic fingerprints verify identity and purity—both NMR and IR should display distinctive peaks for the aromatic protons, the carboxyl proton, and the phenolic group. In the field, this matters more than most admit. I remember batch testing by TLC only to find unexpected spots, later attributed to an impure starting material. Vendors who offer certification and detailed batch analysis jump to the top of shopping lists after such experiences.
Storage remains simple: keep away from direct sunlight and moisture, tuck the bottle in a cool, dry chemical cabinet, and avoid unnecessary opening. While it doesn’t break down rapidly under light or mild heat, best practice never hurts. One less variable to chase down when something goes awry in an experiment.
Processing benzoic acid derivatives often proves tricky, but not so much with this material. Its consistent behavior in Ullmann coupling, esterification, and amide bond formation opens up space for creativity on the bench. Medicinal chemists find value in the core because it serves as a stepping stone to complex scaffolds for clinical candidates or probe molecules. Those working on fluorescent probes or analytical dyes consider its electron-rich nature a big win.
The role of both the bromine and hydroxyl groups gets highlighted in combinatorial chemistry and pharmaceutical development. Brominated aromatics like this often feature as intermediates in making nonsteroidal anti-inflammatory drug derivatives, antimicrobial candidates, or even advanced polymers. I’ve seen teams use it to nudge a synthetic route over the finish line, improving both overall yield and the purity of target molecules.
In academic settings, 3-Bromo-2-hydroxybenzoic acid frequently makes its way into undergraduate labs, allowing students an introduction to multi-step synthesis techniques. It’s not a particularly hazardous compound, so responsible handling—not excessive safety paraphernalia—usually suffices. This makes it approachable for those learning to fine-tune their pipetting and technique, giving budding chemists a low-stress entry point into organic transformations.
Industry puts it to work in pilot plants or kilo-labs, especially during process development studies for new APIs or advanced materials. These environments prize not only purity but reproducibility, and this compound’s strong performance in both categories builds trust. Teams working under tight regulatory frameworks appreciate knowing exactly what’s coming out of a bottle, batch after batch.
Plenty of chemical catalogs stock a dizzying variety of substituted benzoic acids. Sitting through purchasing meetings, I’ve listened to both enthusiastic endorsements and skeptical questions about why this specific compound deserves shelf space. It ends up being about control and predictability. While similar products can provide some advantages, few offer the same mix of bromine’s functional group and the activating hydroxyl group.
Let’s talk about 2-hydroxy-3-methylbenzoic acid or 3-bromo-4-hydroxybenzoic acid—both used broadly in organic chemistry. Each has strengths. The methyl variant pushes electron density further, changing reaction rates. The isomeric bromohydroxy acid creates a different pattern for directing further reactions, influencing not only where reactions take place but how easy purification becomes. 3-Bromo-2-hydroxybenzoic acid commands its own niche because it combines electronic effects and steric accessibility in a tightly defined manner. Colleagues in analytical chemistry value a substance that delivers reproducible results while minimizing byproducts.
For those working in pharmaceutical development, every synthetic step takes both time and money. Picking an intermediate that saves labor by reducing purification steps, increases yields, or avoids costly protecting group manipulations can really set a group apart in tight timelines. That’s the difference this compound offers. Its performance rarely draws complaints—less troubleshooting, fewer unexpected contaminants, and improved scalability for larger batches.
A day in an organic laboratory can go from smooth to chaotic when a substance introduces instability. That gets reflected in the strong safety and performance record 3-Bromo-2-hydroxybenzoic acid maintains. It doesn’t give off noxious odors, nor does it require a laboratory overhaul in terms of containment or controls. The bromine atom tugs at the molecule’s toxicity profile but without crossing the threshold that triggers concern for routine handling.
Every chemist remembers managing a runaway reaction due to an unstable or unanticipated impurity. This compound sidesteps such pitfalls by remaining solid and easy to weigh even after extended storage under standard conditions. SDS sheets from suppliers inform about basic irritancy and the importance of gloves and goggles—good advice for any lab work. I’ve never heard of major incidents arising from its use, and most experienced researchers would agree that good labeling, dedicated storage, and neat technique cover almost every risk.
Being stable against light and not readily hydrolyzed or oxidized, it finds favor in long-duration studies. Analytical teams count on consistent response factors in HPLC or GC assays, while preparative chemists monitor their processes with confidence in the material backing them up.
Synthetic chemistry keeps evolving. Regulatory demands, cost-pressures, and a push toward greener methods all shape which materials gain ground. 3-Bromo-2-hydroxybenzoic acid adapts well to these changing dynamics. Its ability to serve as both a functional intermediate and a scaffold for innovation matches well with efforts to reduce unnecessary step-counts in synthetic sequences. Thinking about retrosynthetic analysis, I often return to this building block because it often trims complex projects down to size.
Continued interest in halogenated compounds comes from their roles in controlling biological activity and improving material properties. The pharmaceutical sector looks for options to optimize selectivity and binding affinity without introducing toxic impurities—this compound checks both boxes. As medicinal chemistry projects grow in complexity, sources of brominated, hydroxyl-bearing aromatics grow ever more valuable. The potential for sustainable synthesis exists; clever modifications to existing processes, use of alternative solvents, and recycling effluents all look promising for future uptake, especially as suppliers respond to increased demand from life-science and material-technology fields.
Chemists want fewer setbacks and more reliable results. They look for partners not just in people, but also in compounds that give their best at each step. 3-Bromo-2-hydroxybenzoic acid serves this role well. Its economic cost sits comfortably within reach for both high-volume commercial efforts and focused bench research. It bridges practical laboratory needs with advanced chemistry ambitions, proving that even quietly reliable compounds carry real weight in shaping research today.
From years of experimental work, a few hard-won tips stand out. When recrystallizing 3-Bromo-2-hydroxybenzoic acid, consider using a mixture of ethanol and water—the slight differential in solubility helps with large-scale purification and saves solvent. Filtration through fine-grade sintered glass preserves yield without introducing filter fibers. For chromatography, a combination of ethyl acetate and hexanes offers effective separation without trailing.
During coupling reactions, a base like potassium carbonate simplifies product isolation and limits over-reaction. One challenge in multi-step synthesis relates to protecting groups. Fortunately, the presence of ortho-phenolic substitution allows flexible use of acetyl or benzyl groups, easily added and removed under mild conditions. Anyone managing large sample throughput learns quickly that straightforward deprotection beats clever, experimental steps.
Handling remains simple thanks to the crystalline nature of the material—no slippery oils or sticky solids. Transfer losses drop, and weighing becomes fast and accurate. Any chemist with a busy schedule recognizes the time savings this brings. Plus, the material holds up well on the shelf, so keeping a decent stock for six months or more rarely presents issues.
Trust in raw materials shapes scientific progress as much as creativity or funding. 3-Bromo-2-hydroxybenzoic acid, thanks to its reliable performance, builds credibility in results—the kind that holds up under peer review and regulatory audit alike. Past experiences with batches from trusted suppliers confirm the value of ongoing partnerships, especially when documentation stands ready for inspection and storage protocols follow good laboratory practice.
Proven performance in small- and large-scale reactions, straightforward purification, and a useful chemical profile all speak to lasting utility. Students, researchers, and industry teams value more than theoretical capacity; the real reason labs come back to this material lies in its consistent results, the transparency from suppliers about batch quality, and the troubleshooting relief that accompanies a trusted reagent. Over time, that track record helps turn everyday compounds into foundation stones for bigger scientific gains.
As chemistry’s landscape shifts toward efficiency and sustainability, the tools researchers reach for will reflect growing needs for performance and reliability. 3-Bromo-2-hydroxybenzoic acid sits comfortably inside that toolkit, offering more than just another halogenated aromatic. Its advantages become clear during challenging reaction sequences, long process runs, and when building new classes of functional molecules.
Keeping quality consistent, supporting innovation, and prioritizing transparent supplier relationships all help ensure that products like these keep science moving forward, not in leaps, but in every confident step from bench to breakthrough.