|
HS Code |
111762 |
| Productname | 2-Amino-3-(3-Bromobenzylamino)Pyridine |
| Molecularformula | C12H12BrN3 |
| Molecularweight | 278.15 g/mol |
| Casnumber | NA |
| Appearance | Off-white to pale yellow solid |
| Meltingpoint | NA |
| Boilingpoint | NA |
| Solubility | Soluble in common organic solvents like DMSO and DMF |
| Purity | Typically ≥ 98% |
| Storageconditions | Store in a cool, dry place away from light |
| Smiles | NC1=NC=CC(NCC2=CC(=CC=C2)Br)=C1 |
| Inchi | InChI=1S/C12H12BrN3/c13-10-3-1-2-9(6-10)7-16-12-11(14)4-5-15-8-12/h1-6,8H,7,14H2,(H,15,16) |
| Synonyms | 2-Amino-3-[(3-bromobenzyl)amino]pyridine |
| Density | NA |
| Refractiveindex | NA |
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| Shipping | |
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Having spent more than a decade in chemistry research, I know the importance of building blocks that deliver both reliability and flexibility in complex synthesis. In the world of fine chemicals, 2-Amino-3-(3-Bromobenzylamino)Pyridine stands out for those exact reasons. I remember the first time I worked with this compound; the project was a multi-step synthesis hunting for a new kinase inhibitor. Many chemists and researchers may not give it a second look, but a closer inspection shows it can quickly become a powerful tool in your chemical arsenal.
What sets 2-Amino-3-(3-Bromobenzylamino)Pyridine apart? The backbone uses pyridine, a ring structure celebrated for its electron-rich character and reactivity. Adding an amino group and a 3-bromobenzylamino substituent gives it a dual personality—on one hand, it’s reactive enough to support challenging transformations, and on the other, stable enough to store or transport without fuss. Over various research collaborations, I’ve seen this compound open doors in the design of kinase inhibitors and antivirals, not just because of its core, but because the bromine atom offers a direct handle for further modifications.
The presence of a bromo group at the meta position on the benzyl ring isn’t just a trivial detail. It provides unique electronic properties, creating hotspots for selective substitution. During a recent roundtable with a group of medicinal chemists, the consensus was clear: small changes to substituents like these have transformed “good enough” candidates into true lead compounds. The bromide offers possibilities for Suzuki coupling, nucleophilic substitution, or radical bromination—each route unlocking new analogs and potentially novel bioactivity.
Some compounds fight you in the lab, resisting crystallization, forming annoying emulsions, or giving unexpected impurities. That’s not the experience here. In my own runs, 2-Amino-3-(3-Bromobenzylamino)Pyridine handled solid processing and chromatography with little drama. The free-flowing solid is manageable, which makes setting up reactions less of a headache, and the aromatic core gives solid UV absorbance—extremely helpful for TLC monitoring or HPLC quantification.
Another advantage relates to solubility and compatibility with diverse reaction conditions. The molecule dissolves readily in common polar organics, like DMSO, DMF, and ethanol, while showing enough stability to tolerate gentle heating or mild acids and bases. That opens up opportunities, whether you are running nucleophilic aromatic substitutions or dialkylation reactions. Years of benchwork have shown me that finding a reliable intermediate means fewer late-stage surprises and more reproducible results—a priceless benefit in scale-up or collaborative projects.
Consistency can make or break a project. Purity matters, but so does the batch-to-batch behavior. Early in my career, projects were sent off track due to subtle shifts in melting point or undetected by-products lurking in sensitive molecules. With this pyridine derivative, high chemical integrity means trustworthy results. Independent HPLC and NMR data from published studies confirm clean spectra and single-product outcomes under a range of standard lab conditions. This is a reassurance I look for, especially when grant deadlines are looming or a partner expects cross-lab verification.
Plenty of chemists default to simpler aminopyridines or chloro-substituted analogs. The difference comes down to the functional group flexibility and the added reactivity at the benzyl position. Chloro analogs might seem interchangeable, but bromide often delivers superior leaving group behavior, making for more efficient coupling and easier downstream modifications. That advantage means fewer failed runs, less waste, and more time chasing real novelty rather than troubleshooting dead ends.
I used to reach for 2-amino-3-benzylaminopyridine when mapping out hit-to-lead routes. Once I started working with the brominated derivative, late-stage diversification became much smoother. The ability to rapidly crank out libraries by tweaking the aryl or pyridine portions helped us hit three new active scaffolds in a single quarter. While this isn’t a magic bullet, it shows the value of strategic halogen placement in early-phase discovery.
Walking through academic and industrial labs, you see how flexibility in intermediates speeds innovation. Teams engaged in oncology and CNS research keep an eye out for molecules that strike a balance between reactivity and stability. 2-Amino-3-(3-Bromobenzylamino)Pyridine fits this role well: one lab’s project leader described it as a “shortcut” to small molecule modulators with complex substitution profiles. In my own consulting work, biotechnology startups favor intermediates like this because they support quick pivots—from heterocycle formation to late-stage functionalization—critical when screening large platforms on tight timelines.
Beyond synthesis, this compound’s profile proves useful for those working on functional materials or catalyst design. Pyridine-based ligands combined with aryl bromides feature prominently in organic electronics and cross-coupling catalysis. Flexibility in derivatization lets chemists tune electron density and spatial orientation, unlocking new avenues in ligand-driven transformations. A friend in academic catalysis research once remarked that intermediates like this are the unsung heroes—the foundational stones behind journal cover articles and patent applications.
Every chemist has stories of near misses and messy cleanups. One reason I like working with this aminopyridine is its predictable handling; there’s no need for cryogenic storage or special ventilation. While reasonable precautions apply—use of gloves, working in a fume hood, minimizing dust and contact as with any aromatic amine or organic halide—the stability at ambient conditions means no more drama than a typical substituted heterocycle.
That being said, judicious storage practices always make sense. I store such materials in tightly sealed amber vials away from light and moisture, which guards purity during longer studies. Whenever a new lot comes in, a quick melting point check and TLC run have proven more than enough to confirm identity and quality. Newer labs might worry about the environmental or health impact, but in published EHS data, this compound sits in the moderate hazard bracket—far milder than many acyl halides or oxidizing agents.
After spending time at both startups and established pharma labs, I’ve watched too many promising scaffolds flop as teams scale from milligram to kilogram quantities. Intermediates like 2-Amino-3-(3-Bromobenzylamino)Pyridine tell a different story. Lab-scale procedures scale nicely, whether you’re running reflux in a round-bottomed flask or feeding a jacketed reactor. Analytical follow-up finds few surprises—byproducts remain manageable, and workups require no exotic purification tricks, just standard washes or columns. Such predictability helps when pitching for production budgets or moving projects into pilot-scale synthesis.
Companies hunting for scalable starting materials look for more than just price. They need availability, regulatory documentation, and quality transparency. Over repeated business cycles, I have dealt with intermittent shortages or purity issues elsewhere, but commercially available lots of this aminopyridine consistently meet specifications. Suppliers track lot histories, run extensive QC testing, and provide spectral data, giving process chemists what they need to build robust production schedules.
Collaboration fuels modern drug discovery. Some of the best results I’ve seen involve multidisciplinary teams—from molecular modelling to scale-up operations—working off a shared toolkit. 2-Amino-3-(3-Bromobenzylamino)Pyridine’s established reactivity and ease of customization lend it to quick iteration cycles. Synthetic organic chemists can run parallel coupling experiments, while analytical teams efficiently confirm structure and purity. The process chemist’s priorities line up: robust to a range of conditions, straightforward to isolate, minimal regulatory headaches. In multi-institutional projects with fast-track targets, these traits smooth communication and accelerate translation from concept to candidate.
I think back to student projects, where budget and time constraints put every intermediate decision under a microscope. Using robust and versatile building blocks trimmed weeks off project timelines. Students could focus on hypothesis testing instead of troubleshooting failed reactions. The feedback loop tightened; mistakes became learning moments rather than dead ends.
Industry leaders and startups alike want chemistry that treads lightly on the environment. I have seen plenty of once-popular substances phased out due to persistent toxicity or byproduct waste. This pyridine derivative, with its single aryl bromide and moderate toxicity, represents a responsible choice. Synthesis routes frequently use greener solvents and generate minimal hazardous waste compared to transformations involving heavier metals or persistent halogens.
Waste treatment also becomes simpler; brominated aromatic waste, while calling for responsible management, aligns with established disposal protocols. The compound’s stability translates into less product loss, reducing re-synthesis and associated chemical waste. I recall one pilot project where switching to this intermediate cut hazardous solvent requirements by half—unexpected savings that caught the attention of management and environmental compliance officers alike.
In my consulting work, chemical biology groups often push the limits of what a small molecule can do. They need scaffolds that deliver rich structure-activity relationships. The aminopyridine core, with its blend of hydrogen-bond donors, aromatic stacking possibilities, and easy derivatization, inspires creative library design. Biologists playing with structure find that tweaking the aryl bromide position on the benzyl ring brings surprising shifts in target affinity and selectivity.
A project in neuropharmacology comes to mind—teams synthesized dozens of analogs using this core to hunt for novel neurotransmitter modulators. Structural variations around the bromide led to analogs with both improved activity and cleaner off-target profiles. Medicinal chemists have confirmed, publication after publication, that the scaffold grants access to new spaces in chemical biology, spaces that help close the gap between in silico models and real-world function.
The constant pressure in life sciences research demands quick movement from idea to outcome. Chemicals that facilitate parallel exploration and rapid prototyping gain an edge. 2-Amino-3-(3-Bromobenzylamino)Pyridine helps by supporting a broad reaction toolkit, offering straightforward routes to both small tweaks and larger departures.
Having served as a bridge between initial design and final optimization, this compound often anchors research as teams chase down newly discovered biochemical pathways or rare interactions. Modern labs—whether university-based or in pharma clustering—value products that synchronize well with both high-throughput synthesis and niche custom reactions. Well-characterized, robust intermediates mean less time managing variables and more time analyzing outcomes. That difference manifests in more confident conclusions, more publications, and, ultimately, breakthroughs with direct clinical or industrial impact.
Looking forward, it becomes clear how strategic building blocks—beyond mere reactants—guide the pace and direction of discovery. I have seen colleagues use 2-Amino-3-(3-Bromobenzylamino)Pyridine as a stepping stone toward personalized medicine, optimizing hit molecules through focused, structure-based design rather than blind screening.
Emerging fields such as proteolysis-targeting chimeras and selective enzyme inhibitors draw on these robust, modifiable scaffolds to advance. Having a compound that fits easily into existing workflows while holding potential for entirely new chemistry lets labs adapt quickly as research paradigms shift. In educational contexts, instructors use well-behaved intermediates like this to help students grasp both classical mechanisms and the tension between stability and reactivity—a foundation for those entering the next generation of science and technology fields.
After years spent balancing theory and benchwork, my perspective centers on practical value and long-term utility. 2-Amino-3-(3-Bromobenzylamino)Pyridine brings more than a clean NMR spectrum or an exotic IUPAC name—it brings real options to chemists juggling speed, flexibility, and innovation. Its features have answered the demands of new synthetic methodology, complex medicinal chemistry, and industrial scaling, all while keeping risk and hassle to a minimum.
I have witnessed projects that might have languished spring forward thanks to the measured reactivity and practical handling of this compound. From the fast-moving startup to the storied pharmaceutical giant, robust intermediates are the silent partners behind every product advance. For my part, I look for chemical tools that keep projects on track, foster new connections, and enable discoveries not just now, but well into the future. On all those fronts, this aminopyridine continues to deliver, earning its place on both my own shelf and any lab committed to pushing the boundaries of science.