|
HS Code |
627468 |
| Chemicalname | 2-Bromo-5-Methylphenol |
| Casnumber | 6627-55-6 |
| Molecularformula | C7H7BrO |
| Molecularweight | 187.04 |
| Appearance | White to off-white solid |
| Meltingpoint | 59-62°C |
| Boilingpoint | 255.8°C at 760 mmHg |
| Density | 1.6 g/cm³ |
| Purity | Typically ≥98% |
| Solubility | Slightly soluble in water; soluble in organic solvents |
| Smiles | CC1=CC(=C(C=C1)Br)O |
| Inchi | InChI=1S/C7H7BrO/c1-5-2-3-6(8)7(9)4-5/h2-4,9H,1H3 |
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2-Bromo-5-Methylphenol stands out as an organic compound with practical uses for developers, researchers, and manufacturers working in pharmaceuticals and chemicals. Its molecular structure—bearing both a bromine and a methyl group attached to a phenol ring—gives it qualities you won’t find in simple phenols or basic brominated benzenes. People who work in organic synthesis appreciate the versatility this compound delivers. The presence of the bromine atom in the ortho position to the hydroxyl group brings selectivity in substitution reactions, making this compound a preferred starting material in labs that can't afford unreliable intermediates or inconsistent reaction yields.
Looking at its chemical makeup, 2-Bromo-5-Methylphenol (C7H7BrO) has a molar mass of about 187.04 g/mol. Its crystalline nature often allows for straightforward handling and measurement on the lab bench. The solid form carries a faint aroma that signals phenolic character, something most chemists will recognize. Melting points may range from 70°C to 75°C, which gives users some flexibility in purification and handling. Solubility in common organic solvents like ethanol, ether, and chloroform supports applications that benefit from quick dissolution and even dispersion, whether in complex synthesis or quality control testing.
Anyone who spent long hours planning syntheses knows that the right starting materials can mean the difference between days wasted and real progress made. I first encountered 2-Bromo-5-Methylphenol while looking for a phenolic intermediate that could offer reactivity without causing side reactions. Some phenols, when brominated, yield unpredictable results. This compound gets around that by placing methyl and bromo groups exactly where they provide stability as well as the freedom to direct follow-up substitutions. The methyl group at the 5-position shields the ring from overbromination or unwanted cross-coupling, a headache for anyone dealing with delicate downstream reactions.
Not every chemical hits the mark for both performance and convenience, but here, handling remains fuss-free. Even as a bench chemist early in my career, I could weigh, dissolve, and react this compound with little worry about air sensitivity or rapid degradation. In contrast, related compounds with activating groups elsewhere on the ring tend to suffer from rapid oxidation or give unpredictable byproducts. This kind of practical stability saves time and reduces waste—two things every researcher values whether they work in pharmaceuticals or materials science.
Many researchers search for intermediates that can deliver both efficiency and purity in their target synthesis. 2-Bromo-5-Methylphenol has found fans among medicinal chemists who need to build phenolic scaffolds for trial compounds. The combination of a bromine and a methyl group shapes pharmacological properties, allowing easy access to libraries of analogs that can be tested for antifungal, antibacterial, or anticancer activity. Structure-activity relationship studies have shown that subtle changes on the phenolic ring can pivot a molecule from poor to potent in physiological assays. A team looking to optimize such bioactivity values the way this compound streamlines synthesis, getting from blueprint to bench in fewer steps.
Some crop protection research also benefits from specific phenols. For example, organic chemists working in agrochemical design reach for 2-Bromo-5-Methylphenol to introduce heterocycles, ethers, or esters onto the ring. The pattern of substitution provided by its structure makes certain transformations more selective, which cuts down on purification steps. Not all halophenols offer this advantage—many give mixtures or require counterproductive protecting group strategies that burn time and resources.
Polymers and specialty chemicals also rely on building blocks that combine reactivity with physical stability. Here, the compound’s unique substitution pattern lets it act as both a precursor to more elaborate monomers and a direct additive in certain formulations. Inhibitors, antioxidants, and stabilizers for plastics sometimes call for specific halophenol patterns; 2-Bromo-5-Methylphenol supports these roles without causing cross-reactions that can compromise material properties.
Researchers and technicians often ask: What separates this chemical from similar brominated phenols or other methyl-substituted aromatics? Experience teaches that not every bromo-methylphenol delivers in terms of reactivity or handling. Positional isomers—that is, compounds where the bromine or methyl falls elsewhere on the ring—often fail to show the same selectivity in nucleophilic substitution. Those working in organic synthesis will notice the difference. For instance, 4-bromo-2-methylphenol or 3-bromo-5-methylphenol can require more aggressive reagents to make desired transformations work, increasing the risk of side products.
The pattern here—bromine ortho to the hydroxyl and methyl meta to both—results in a molecule neither too reactive nor too inert. This balanced reactivity speeds up coupling reactions when making biaryl linkages or heterocyclic frameworks. Researchers working on Suzuki or Buchwald–Hartwig reactions, for example, often see higher yields using this intermediate compared to more heavily substituted or differently substituted analogs. In my own trial runs, the difference in yield can reach double digits, an outcome that translates to shorter production schedules and lower costs.
Years of published studies back up the experiences many practitioners report in the lab. Chemists working in pharmaceutical research frequently cite 2-Bromo-5-Methylphenol as a best-in-class intermediate. A search through major journals turns up papers demonstrating its use in the preparation of benzoxazoles, phenolic ethers, and more. It often serves as a launching pad for making C–N and C–O bonds, with literature yields that run higher than similar bromophenols. Not only does the compound offer clean reactivity, it also comes with predictable NMR and mass spectra, which makes characterization fast and reliable.
In addition to this track record, reviews on phenolic building blocks for medicinal chemistry note that bromo-methyl substitution patterns rank higher for downstream flexibility compared to nitro or amino analogs. Researchers highlight predictable Suzuki coupling behaviors and less background reactivity in electrophilic aromatic substitution. Such outcomes resonate with practical experience—nobody likes spending extra time cleaning up reaction mixtures full of inseparable side products.
Safe handling matters just as much as reactivity. Phenols, by nature, demand some respect due to their corrosive potential and toxicity. 2-Bromo-5-Methylphenol isn’t exempt. In work settings, ordinary fume hood practices and protective gloves take care of most hazards. Some users may notice mild irritation if it comes in contact with skin, which matches general experience with this class of compounds. Rarely do issues arise beyond what standard lab protocols already expect. Compared with more reactive halophenols or methylphenols containing activating nitro or amino groups, this compound usually stays manageable in everyday handling.
Availability ranks as another important concern for scientists on tight schedules. Accessing reliable material supply can determine whether a project moves forward or stalls. Suppliers around the world recognize the demand for this compound, and most provide a product manufactured to high purity—sometimes above 98%. Batch consistency and supply volume carry weight in larger operations. Nobody wants to rerun a reaction due to lot-to-lot variation or run short midway through a synthesis campaign. I have seen a few suppliers come up short on documentation or analytical support, though, so it pays to check for detailed certificates of analysis before ordering at scale.
The leap from routine chemical supply to robust, responsible sourcing shouldn’t just serve buyers but should also support safer environments and communities. Sourcing from companies that publish thorough safety and environmental data has become the new standard in labs where compliance with REACH, GHS, and other international norms grows ever more important. I found that tracking this information before introducing a new compound can streamline audits and reassure institutional safety committees. Clear hazard communication not only guards individuals from risk but also fosters a culture of care in research and manufacturing.
Waste reduction forms another part of responsible use. Phenolic waste, especially halogenated byproducts, can challenge municipal and facility-level disposal systems. Teams serious about minimizing impact invest in solvent recovery programs and contract with certified hazardous waste processors. Some industrial labs have begun exploring in-house treatment technologies that neutralize phenols and remove halogens before discharge—steps that both reduce liability and strengthen credibility with local communities.
On the research front, there’s steady momentum toward methods that use less resource-intensive reagents, lower energy inputs, and safer solvents. Benchmark reactions using 2-Bromo-5-Methylphenol already demonstrate higher yields—meaning less chemical waste and shorter reaction sequences—than many other comparable building blocks. Encouraging green protocols and best lab practices magnifies this advantage, both for individual researchers and the environment they work in.
Some of the most innovative uses for 2-Bromo-5-Methylphenol occur where different fields cross paths. Medicinal chemistry still leads in terms of usage volume, but groups cultivating new materials or sustainability-focused chemistry find value as well. For example, collaborative teams working on organic electronics sometimes turn to phenolic building blocks as dopants or precursors for electroactive polymers. The unique substitution pattern here helps tailor both electron flow and physical robustness in synthesized materials.
Environmental testing and remediation group members have also begun exploring halophenols as tracers and investigative tools. Here, rigorous analytical validation remains crucial, as even minor impurities in starting material can ripple through sensitive applications. Analytical labs with HPLC and GC-MS capabilities tend to give this compound high marks on purity and reproducibility, establishing it as a preferred choice for controlled studies.
Growth in undergraduate and graduate research projects signals broad faith in the compound's reliability. Hands-on experiments in advanced synthesis classes sometimes use 2-Bromo-5-Methylphenol to introduce students to modern coupling chemistry, aromatic transformations, and analytical method development. The low barrier to entry—straightforward handling, widely available reference spectra, and minimal special equipment—extends the learning curve for tomorrow’s chemists.
Talk with practicing organic chemists, and two themes surface frequently: time savings and reliability. Projects live or die by how quickly and cleanly key intermediates form. Over the years, word of mouth pushed 2-Bromo-5-Methylphenol to the fore for those aiming to get work done without unnecessary detours or do-overs. The consensus holds: fewer purification headaches, stronger selectivity, and batches that behave predictably across a wide range of reaction types.
Those who demand more than commodity chemicals also appreciate the attention to safety and documentation offered by reputable suppliers in this space. In my own experience, the divide between well-documented and poorly supported supply chains can cost days or weeks—no small issue during crunch time. Reliable certification of assay, moisture content, and even residual solvent data pays dividends in fewer surprises down the line.
Failures and challenges do happen, of course. One project team I worked with encountered unexpected overreactions when scaling up from test tube to pilot scale—a mismatch in mixing rates led to inconsistent yields. Rather than blame the compound, we traced the issue to process control. Adjusting reagent addition rates and improving agitation smoothed out production, a lesson in the importance of sound planning over pinning faults on materials.
Research priorities shift, but the need for reliable phenolic intermediates holds steady. Changes in drug discovery pipelines, renewable materials development, and even battery chemistry all contribute to the steady demand for structures like 2-Bromo-5-Methylphenol. This compound, once limited to niche applications, continues to enjoy broader adoption wherever efficiency and precision steer projects.
Chemists working at the intersection of fine chemicals and high-performance materials keep the spotlight on compounds that punch above their weight in both reactivity and practicality. Down the road, growing pressure for greener syntheses and safer handling will only raise the bar. Suppliers and labs responding to these pressures will favor intermediates that deliver not just on basic functionality but also on social and ecological responsibility—two aims that reinforce each other across industries.
Experiences with 2-Bromo-5-Methylphenol underpin a simple lesson: quality, consistency, and practical knowledge foster successful applications. Its steady performance, well-documented reactivity, and role in supporting breakthrough discoveries make this phenol a go-to tool for those who demand more from their building blocks. Researchers and product developers will continue staking their progress on materials that justify confidence—putting trust in products that have earned it, like 2-Bromo-5-Methylphenol.