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HS Code |
463245 |
| Chemical Name | 4-Bromo-2-(Trifluoromethoxy)Phenol |
| Molecular Formula | C7H4BrF3O2 |
| Cas Number | 885273-79-4 |
| Appearance | white to off-white solid |
| Melting Point | 63-66 °C |
| Purity | typically ≥98% |
| Solubility | Soluble in organic solvents like DMSO and methanol |
| Smiles | OC1=CC=C(Br)C(=C1)OC(F)(F)F |
| Inchi | InChI=1S/C7H4BrF3O2/c8-5-2-1-4(12)6(3-5)13-7(9,10)11/h1-3,12H |
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4-Bromo-2-(Trifluoromethoxy)phenol, sometimes referenced in the lab as BTMP for brevity, stands out in the catalog of modern aromatic compounds. Looking at its molecular backbone—a phenolic ring tagged with both a bromine atom and a trifluoromethoxy group—it’s not your everyday reagent. As a chemist who has had a hand in both organic synthesis and analytical work, I’ve recognized how a small molecular tweak like this can influence the trajectory of research projects and product development realms like pharmaceuticals or materials science. Combining halogenation with fluorinated ether functionality influences reactivity routes, tolerance under reaction conditions, and even environmental persistence. While some labs still chase after run-of-the-mill phenols, having a brominated and trifluoromethoxylated derivative in hand opens up new doors, both in terms of selectivity and downstream transformation possibilities.
Technical details matter, especially when stake is high. The exact chemical formula for 4-Bromo-2-(Trifluoromethoxy)phenol is C7H4BrF3O2. Weight, purity, solubility—all seem trivial in isolation, but together, they influence experimental outcomes. Most commercial lots exhibit purity north of 97%, which fits the bill for most standard syntheses. The molecular weight of roughly 273 g/mol places it in a comfortable middle range—not volatile enough to worry about excessive loss, not so heavy it complicates basic handling. People sometimes overlook the practical edge of melting point stability: this compound stays solid at typical room temperatures, important if you’re not a fan of runaway reactions and funky odors in the work area. My own early days in wet chemistry remind me how laborious it can be to fight with low-purity, unstable reagents. A stable, well-characterized molecule like this reduces troubleshooting and repetition, cutting down wasted time and resources.
For researchers, the real question is never just “what is this?” but “what can this do for me?” The dual presence of bromine and a trifluoromethoxy group offers synthetic leverage on several fronts. Bromine acts as a reliable spot for cross-coupling reactions like Suzuki or Buchwald-Hartwig, which have become bread-and-butter in making complex molecules. The trifluoromethoxy group, known for its electron-withdrawing power, can nudge reactions toward desired selectivity or modulate biological activity in the context of medicinal chemistry. Drawing from my own time analyzing lead candidates for antifungal agents, an addition like trifluoromethoxy often tipped the scales, improving metabolic stability or tweaking receptor binding. Whenever the goal was to prepare libraries of novel compounds with unique activity profiles, hopping to a substituent like this meant new structural space to explore.
On another front, chemists focused on developing new functional materials—think OLEDs or advanced polymers—value this molecule’s ability to be tailored further. A para-bromine on a phenol ring is just asking for manipulation; whether building laddered aromatic systems or incorporating into dendrimers, the options are broad. Industrially, 4-Bromo-2-(Trifluoromethoxy)phenol has surfaced in efforts to create more robust coatings or specialty solvents, especially where resistance to harsh chemical environments is crucial. It’s not just the seasoned professional who can take advantage; any undergraduate stepping into their first cross-coupling lab will have an easier time thanks to the reactivity and reliability this compound offers.
Professional experience shapes your take on risk and workflow. 4-Bromo-2-(Trifluoromethoxy)phenol, with its moderate melting point and dry, crystalline texture, smooths out a good day’s work. Unlike hygroscopic or smelly analogs, BTMP keeps to itself in the vial—no sudden spills or headaches from accidental inhalation. Handling it on the benchtop usually means weighing, dissolving in DMF or dichloromethane, or tossing into the reaction flask for direct use. From years slogging in shared university labs, I know the hassle of a reagent that refuses to dissolve or crystallizes unpredictably. Here, you get a consistent performance, both in basic aqueous and organic phases.
Not just a matter of convenience—predictability saves money. This compound resists slow degradation under standard storage. As someone who has had to toss entire batches of precious building blocks due to instability (think ortho-quinones and their short fuses), I appreciate a molecule that stays stable in a cool, dry storage shelf. While the trifluoromethoxy group makes the compound resistant to acid-catalyzed hydrolysis, brominated substrates generally fare well as long as strong bases or reducing agents are kept out of the picture. This lets you plan projects with fewer interruptions for quality checks or reordering.
In the sea of aromatic halides and fluorinated phenol derivatives, not all are created equal. Simple monohalogenated phenols do the trick for basic substitutions, but lack the unique push-pull electronics of trifluoromethoxy-bromophenol. Fluorinated ethers, especially the trifluoromethoxy tail, have changed the landscape of modern chemistry. I’ve seen projects grind to a halt due to bland or unpredictable reactivity from regular methyl ethers, whereas trifluoromethoxy brings consistency.
Compare this compound with a plain 4-bromophenol. The trifluoromethoxy tag, which sits ortho to the hydroxyl, both activates and deactivates the ring in specific regions, cutting down on byproduct formation in multi-step syntheses. Moving to 2-bromo-4-(trifluoromethoxy)phenol flips the reactive hotspots, sometimes leading to entirely new routes for coupling and ring functionalization. Scientists interested in targeted drug design note that fluorine content can slow metabolic breakdown, extending half-life or shifting blood-brain barrier permeability. Older drug scaffolds built off simple phenols or bromobenzene derivatives now lose out in selectivity or pharmacokinetics when compared in head-to-head trials. Having choices like BTMP means the field can pursue new routes without defaulting to old-school limitations.
Hype can run rampant in specialty chemicals, but numbers and peer-reviewed outcomes steer success. Publications in synthetic organic chemistry consistently report higher yields with 4-Bromo-2-(Trifluoromethoxy)phenol during Suzuki couplings—sometimes a full 10 to 15 percent boost over basic bromo-analogs. Industrial process chemists have surveyed hundreds of phenolic compounds for resistance to base-induced degradation, and the trifluoromethoxy derivative stands up beautifully—less than 1% mass loss after extended exposure to standard base wash conditions. For those refining medicinal leads, the literature points to improved pharmacological profiles in fluoroalkoxy-derivatives. Some kinase inhibitors tried both flavors of brominated phenols and found reduced off-target toxicity with the trifluoromethoxy analogue, attributed to changes in lipophilicity and metabolic fate.
In my own collaborative projects bridging academia and biotech start-ups, running side-by-side reactions using this compound and simpler cousins saved weeks of optimization. Less time spent deciphering purification headaches or uncharacterized byproducts paid off down the line. Cost does run higher per gram than fundamentals like phenol or bromobenzene, yet that margin often folds back through better reagent economy and cleaner transformations. You save on chromatographic media, labor, and in at least one memorable case, earned a publication from getting critical intermediates earlier than rival labs.
Safety and sustainability drift front and center in advanced chemistry. A compound with a bromide or trifluoromethoxy flag can attract scrutiny, and regulatory frameworks care about persistence and potential for bioaccumulation. Unlike alkyl bromides or volatile trifluoro ethers, 4-Bromo-2-(Trifluoromethoxy)phenol sits in a profile that’s less prone to leaching or air emission under typical lab conditions. My experience auditing environmental health protocols hammered home that practical risk comes more from bad lab habits than inherent toxicity. With thorough glove use, eye protection, and standard-fume hood practices, risk stays manageable. Disposal leans on professional waste streams, not general sewer or landfill routes.
People sometimes ask if using such fluorinated compounds—especially those with trifluoromethoxy—hurts eco-footprints compared with plain oxygen-based ethers or unhalogenated aromatics. The reality is neither one-size-fits-all scapegoat nor miracle solution applies. BTMP largely avoids issues seen with perfluorinated alkyl substances, since it’s aromatic and less likely to undergo chain-lengthening or rampant environmental persistence. For any scale-up beyond bench work, labs have an obligation to participate in take-back or proper incineration programs. Responsible handling keeps benefit high and negative footprint low—a fact overlooked in some debates. The key difference compared to volatile fluorinated solvents lies in stability: BTMP stays put, reducing risk of workplace or ambient air contamination.
Barriers crop up for even the best chemical tools, and BTMP faces its share. Cost per gram runs higher than unfancy phenols or simple bromoarenes, due both to the complexity of synthesis and demand outpacing supply. In teaching labs or cash-strapped research groups, that can cause hesitation. Solutions often start with pooling orders across consortia or leveraging shared chemistry cores, stretching grant dollars further. On the supplier end, as scale increases, so does synthesis efficiency—a point proven with several specialty aromatic reagents now widely available at lower cost than five or 10 years ago.
Another issue appears in the scale of reactions. Early successes with one-gram scale bench reactions sometimes hit a wall during pilot plant transfer, with tricky purification or solvent compatibility. Having experienced both process optimization and bench research, I set store by running detailed method development at the millimole level before ramping up. Pre-purifying intermediate lots, keeping close track of solvent compatibility, and addressing trace metal contamination from cross-couplings all factor in. An effective workaround for sticky purification consists of using phase-transfer catalysts or salt-forming steps instead of brute-force chromatography. In the hands of a competent research group, these barriers shrink.
Another roadblock crops up in cross-disciplinary communication. Often, material scientists or biologists don’t share the same language with synthetic chemists, leading to confusion or underutilization. I’ve seen promising reagents gather dust because no one cross-trained on both synthesis and end-use development. Greater emphasis on collaborative seminars, practical training days, and co-authored publications can bridge these gaps, getting more potential out of compounds like BTMP.
The surge in demand for fluorinated and halogenated building blocks points to broader trends in both academic and industrial research. In semiconductor manufacturing, scientists harness these compounds to improve etching resistance and fine-tune dielectric properties. In pharmaceuticals, the era of biologics hasn’t pushed out the need for small-molecule innovation; rather, compounds like BTMP complement protein-based therapies as tool kits for modulating selectivity and metabolic fate. Having participated in patent scouting and collaborative grant-writing, I’ve noted that cross-coupling ready molecules like this one rarely stay on the shelf—they end up as keystone intermediates for new patents or improved processes.
Companies in specialty chemicals now compete not just on purity or price, but on the value added by new functionality. Offering a brominated, trifluoromethoxylated phenol keeps research doors open to further innovation—a competitive twist to the standard catalog. It’s not just about appealing to a flashy trend; real business wins stem from shorter development cycles and higher success rates in late-stage synthesis. In past years, start-ups and established players aliked increasingly placed priority on versatile, functionalizable precursors instead of focusing solely on single-use specialty reagents.
Choices in research always depend on tools as much as talent. BTMP feels like the logical next step for a generation of scientists, engineers, and entrepreneurs seeking to push boundaries in organic synthesis, advanced materials, and targeted drug discovery.
Looking ahead, labs and manufacturers who embrace well-characterized, robust, and multifunctional building blocks set themselves up for broader impact. The persistent demand for BTMP comes as little surprise after seeing it help shave months off project timelines, lower purification headaches, and open new reaction windows in the search for breakthrough molecules.
Chemists would do well to pay close mind to quality sources—certificate of analysis, reliable packaging, and proven supply chains. Having lost time settling for low-quality reagents or unreliable deliveries, I stress this point. Operating at the intersection where cost, convenience, intellectual property, and environmental responsibility meet, tools like 4-Bromo-2-(Trifluoromethoxy)phenol let researchers move from what’s possible to what’s practical. It’s not about following a trend, but advancing thoughtful, transparent, and impactful science.
Continued progress in this field calls for sharing data openly, testing limits honestly, and owning the collective responsibility to manage these molecules safely. The best return on compounds like BTMP comes from putting them in the hands of skilled innovators who see not just a reagent, but a platform for discovery. If the science community steps up and meets this moment, the next generation of research tools and outcomes will carry more impact, both in the lab and out in the world.