|
HS Code |
683643 |
| Iupac Name | 2-amino-N-(2-bromophenyl)benzamide |
| Molecular Formula | C13H11BrN2O |
| Molecular Weight | 291.15 g/mol |
| Cas Number | 71675-86-0 |
| Appearance | Off-white to light brown powder |
| Melting Point | 192-195°C |
| Solubility | Slightly soluble in water, soluble in organic solvents |
| Purity | Typically ≥98% |
| Smiles | C1=CC=C(C(=C1)NC(=O)C2=CC=CC=C2N)Br |
| Inchi | InChI=1S/C13H11BrN2O/c14-10-7-2-1-6-9(10)16-13(17)8-3-5-12(15)11(8)4-6/h1-7H,15H2,(H,16,17) |
| Storage Temperature | 2-8°C |
| Synonyms | N-(2-Bromophenyl)-2-aminobenzamide |
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Inside every well-stocked research lab sits a handful of building blocks that prop up discoveries. For organic synthesis, scientists scout for compounds that deliver clean reactions, open doors for new kinds of molecules, or offer a clear edge over the usual suspects. 2-Amino-N-(2-Bromophenyl)Benzamide (CAS: 95327-61-2)—often caught in shorthand among chemists—is a prime example. Its aromatic backbone punctuated by an amino group and a brominated phenyl ring has found steady footing across chemical, pharmaceutical, and materials science work.
Just staring at this compound’s structure, it’s easy to see why chemists put it to work. The benzamide core means it brings familiar reactivity, with the amide group blending stability with flexibility. Tied onto this foundation, the 2-amino group opens up routes for derivatization. The 2-bromophenyl part, meanwhile, sets it apart from basic benzamides, giving it a handle for further reactions through the bromine atom.
Bromine has its quirks, adding bulk and electronegativity. Certain synthetic pathways depend on this feature, often calling upon the bromine’s leaving-group abilities when building complex scaffolds. Try trading out the bromine for a hydrogen and you lose more than atomic mass—you shut down access to halogen-exchange chemistry and palladium-catalyzed cross-coupling reactions. From a practical point of view, sticking with the bromo derivative helps inventors stay nimble.
In the cluttered world of starting materials, chemists aren’t just looking for what works—they want compounds that save time, cut down on tricky purification steps, and stay reliable from one batch to the next. 2-Amino-N-(2-Bromophenyl)Benzamide has built a reputation for tight consistency, making project planning less of a coin toss. It dissolves in common solvents like DMSO or DMF, which fits the norms for organic intermediates—handy for setting up parallel screens or running library synthesis. Even those with years of experience developing drug-like molecules have found this compound enables clear SAR (structure-activity relationship) exploration. Its manageable melting point and storage stability earn trust in the lab—no weird sudden shifts, no awkward degradation as long as you keep it capped and out of the sun.
Years ago, I walked into a collaboration between a small biotech and an academic synthetic group. A key project focused on finding new kinase inhibitors required rapid access to aryl-amide cores with scope for side-chain modification. The team started the journey with simple benzamide, only to run into roadblocks converting it in one-pot steps. Their yields flatlined, side reactions ran wild, and purification felt like emptying the ocean with a spoon. The shift to 2-Amino-N-(2-Bromophenyl)Benzamide locked things into place almost overnight. The bromine tagging the ortho position on the phenyl ring allowed their catalyst of choice—usually a palladium-based system—to do the heavy lifting. Instead of wrestling with multiple-step protection and deprotection, they clicked on a range of aryl groups in smooth cross-coupling reactions.
No product is magic, but that small substitution let them swap out a tangle of glassware, cut down on waste, and race ahead in their screens. The lesson? Timber isn’t lumber until it’s cut; in the same way, choosing the right starting material takes you further than brute skill or brute force in the synthesis game.
Drug hunters weigh every new intermediate with an eye on both practicality and safety. Benzamide derivatives carry a strong legacy in small-molecule drug design, popping up in molecules as diverse as anti-inflammatories, anti-tumor leads, and enzyme inhibitors. The combination of the amino and bromo substituents creates room to probe chemical space, whether you’re chasing improved permeability, target engagement, or metabolic stability. In structure-based design, medicinal chemists can turn to 2-Amino-N-(2-Bromophenyl)Benzamide as a kind of workhorse for rapid analog generation. Each tweak around the amide or the positions on either ring gives rise to new SAR data points—even the subtle swap of the bromo for another aryl or heteroaryl group can flip a project’s outcome from ambiguous to promising.
Competitors in this chemical space include other ortho-halogenated benzamides, unsubstituted variants, or amino-phenyl scaffolds missing the bromine. Each has a place, but their behavior under synthesis conditions shifts. Chlorinated analogs offer another angle but can dull down reactivity or complicate coupling efficiency. Fluorinated versions resist transformation in certain steps, often due to the resilience of the C–F bond. The 2-bromo phenyl element in this compound strikes a middle path—reactive enough for diverse cross-couplings, manageable from a safety perspective, and easy to monitor by TLC or HPLC. Brominated compounds also stand out in spectral characterization. For those running routine QC or scale-up, that sharp bromine signature in NMR and MS data can save time and reduce misidentification—a benefit that’s often understated in daily benchwork.
A frequent stop for 2-Amino-N-(2-Bromophenyl)Benzamide lies in developing lead candidates for targeted therapies. Some groups chase protein-protein interaction modulators, others dig after enzyme inhibitors. Add in the rise of targeted protein degradation and the search for molecular glues or PROTACs, and this compound finds itself in the thick of modern discovery strategies. Its use as an intermediate unlocks structures that would be a headache to piece together using less reactive cores. Researchers can append linkers, tack on fluorophore tags, or build out complex macrocycles—all drawing from this single starting point.
Yet, there’s always room for improvement. The bromine ring brings attributes that demand respect: you don’t want to overlook proper handling during scale-up, since organobromides at higher concentrations can drift towards toxicity or require special waste disposal. Labs need decent fume extraction and a no-shortcuts approach to cleanup. The good news—this awareness is commonplace in both industry and academic circles. Transparency in data sheets and direct experience has helped prevent mishaps from careless handling. If someone’s new to halogenated chemistry, a few moments of coaching from a senior chemist clears up best practices faster than any manual.
Unlike finicky organosilicon or metallic intermediates, 2-Amino-N-(2-Bromophenyl)Benzamide holds up under standard bench conditions. It prefers a dry, cool cabinet and a tightly screwed cap. Labs that keep humidity at bay won’t have to fret over degradation before planned reactions. While its brominated nature deserves respect in terms of personal protective equipment and waste, the compound’s solid, non-volatile form makes it safer than some more delicate reagents. That said, once scale-up moves from milligrams to grams—and especially to pilot plant levels—everyone needs to recalibrate risks. Fire safety plans, proper solvent choices, and a sharp look at compatibility come into play. Experience says, better to run a dry trial on a small quantity, talk openly with your chemical supplier, and involve environmental health and safety teams early rather than chase down errors after the fact.
By offering a platform for further reaction, this compound not only accelerates analog synthesis but also gives access to chemotypes that might otherwise be out of reach. Researchers working in oncology, neurology, or even agricultural chemistry recognize the utility of aryl bromides for creating libraries fast. The versatility extends beyond drug discovery. Materials scientists exploring new organic electronics sometimes dip into the benzamide toolkit for compounds with polar groups or unique substitution patterns, aiding assembly of organic semiconducting films or new types of probes. Stable, well-characterized starting materials cut down on troubleshooting, letting chemists channel energy into productive directions.
From my own time navigating new product development, the difference between a productive chemical campaign and a frustrating slog often comes down to the quality of the intermediates and the reproducibility of their transformations. This is where the reputation of 2-Amino-N-(2-Bromophenyl)Benzamide stands out. It doesn’t hog the spotlight, but experienced hands tend to reach for it whenever the end goal relies on rapid aryl, amino, or amide substitutions. Speed, reliability, and clean conversions push it up the list when teams are mapping out the next six months’ deliverables.
For years, the focus in chemical research leaned on brute-force yields and reaction times. Nowadays, the push towards greener, more sustainable approaches is reshaping choices—not just what works, but what works safely and cleanly. Here’s where compounds like 2-Amino-N-(2-Bromophenyl)Benzamide fit in. Its efficiency in palladium-catalyzed couplings means less waste and lower reagent loads. Researchers I know have slashed process steps, dialed down solvent use, and still walked away with high-purity products, all while sticking to this tried-and-tested intermediate. Adapting processes that start from high-functionality, well-tested chemicals reduces byproduct headaches, which in turn trims waste disposal issues.
The move towards one-pot protocols and telescoped synthesis has found an ally in this compound. Its clean reactivity lets chemists skip isolating intermediates, push reactions in faster sequences, and often recover higher yields in less time. This translates to less glassware washing, fewer wasted solvents, and a nod to the growing pressure for resource-conscious science. Solutions like this matter both for tight-budgeted academic groups and for process chemists wrestling with scale-up costs. The old lesson holds: smarter choices at the weigh-out bottle ripple all the way to the last purification column.
Industry veterans know well: a starting material is only as useful as its reputation for quality and consistency. Regulatory transparency matters, since missed contaminants, unexpected reactivity, or poor documentation can bring a promising program to a halt. With 2-Amino-N-(2-Bromophenyl)Benzamide, trusted suppliers run batch-specific purity checks, supply full spectra, and match each lot to expected performance. This builds confidence from the ground up—every research notebook depends on good starting points, not just for quick wins but for credible, repeatable results down the line. Gaps in supply chain transparency, or corners cut on quality checking, have sunk projects before they started. Labs that stick to trusted sources and demand batch-level data avoid preventable surprises.
Organic synthesis rarely goes according to plan. Contaminated starting materials turn up phantom peaks in chromatography. Poor solubility creates headaches moving from mg to g scales. Air- or light-sensitive intermediates force sleepless nights and finicky setups. It’s the middling, quietly reliable compounds like 2-Amino-N-(2-Bromophenyl)Benzamide that help take pain out of scale-up, screen, and purification. Available handling techniques—techs can weigh, dissolve, and transfer without racing to a glovebox or worrying about sudden volatility. Experienced teams appreciate these details: less crisis management means more deliberate, productive thinking about the big problems at hand.
What sets this compound apart isn’t glamour, but substance. The balance of chemical reactivity and operational simplicity mirrors the best lessons in chemistry: progress happens not just with new discoveries, but with quiet improvements to the tools everyone leans on daily. Choosing 2-Amino-N-(2-Bromophenyl)Benzamide for a workflow doesn’t mean sidestepping challenges, but it does take a handful of variables off the worry list. In modern drug research or materials science, that’s more than a small relief—it’s a way to keep talented people focused on high-value tasks, not sidetracked by unreliable basics.
The narrative with 2-Amino-N-(2-Bromophenyl)Benzamide is not about revolutionizing chemistry overnight. It’s about empowering innovation by smoothing the journey from raw material to usable building block. With its blend of functional groups, reliable reactivity, and manageable risk profile, it has made itself at home in the workflows of both public and private sector labs. For the next generation, as new automation and parallel screening technology enter the stage, compounds like this will continue to anchor synthetic strategy. Their predictability becomes even more valuable—not only for core reactions but as scaffolds for tagging, conjugation, or medicinal optimization.
The more time spent at the interface of scale-up, regulatory submission, and creative research, the clearer it becomes: the difference between progress and frustration boils down to choices at the fundamental level. Reliable intermediates, with strong safety documentation, real-world track records, and respectable environmental footprints, deserve attention. By placing 2-Amino-N-(2-Bromophenyl)Benzamide into workflows, chemists keep the focus on delivering impactful discoveries—knowing the routine details are under control.
There’s no replacement for time-tested intermediates that play well with both traditional and leading-edge synthesis. Whether building out a new series of kinase inhibitors, exploring unexplored disease pathways, or dipping into the green chemistry toolkit for sustainable processes, the practical strength of 2-Amino-N-(2-Bromophenyl)Benzamide continues to leave a mark. Young chemists benefit by learning with starting materials that don’t constantly trip them up. Industry vets keep projects on schedule by reaching for what’s proven—saving their creative energy for parts of the job machines still can’t touch.
Each year brings new demands for flexibility, documentation, and environmental care—none of which are likely to slow down soon. The story of compounds like 2-Amino-N-(2-Bromophenyl)Benzamide will keep unfolding, because strong science leans on both the spectacular and the steady. Anyone who has spent a few decades in the lab knows the value of reliability; this compound delivers it in spades, and that makes all the difference for the chemical discoveries driving tomorrow’s breakthroughs.