|
HS Code |
286613 |
| Chemical Name | 2-Bromo-N-Methylacetamide |
| Cas Number | 22115-74-6 |
| Molecular Formula | C3H6BrNO |
| Molecular Weight | 167.99 g/mol |
| Appearance | White to off-white solid |
| Melting Point | 75-80°C |
| Solubility | Soluble in water and organic solvents |
| Purity | Typically ≥98% |
| Storage Condition | Store at 2-8°C, keep container tightly closed |
| Synonyms | N-Methyl-2-bromoacetamide |
| Smiles | CN(C)C(=O)CBr |
| Inchi | InChI=1S/C3H6BrNO/c1-5-3(6)2-4/h2H2,1H3,(H,5,6) |
| Safety Hazards | Irritant; handle with appropriate precautions |
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2-Bromo-N-Methylacetamide isn’t the flashiest name in chemistry, but a closer look uncovers how this compound can matter in real lab work. Sitting under the CAS number 6865-91-8, the molecule draws attention in fields that value strong predictive yields, predictable reactivity, and controllable functional behavior in the synthesis of more complex targets. You run across the formula C3H6BrNO, and the structure shows a bromoacyl group linked to a secondary amide. For students, researchers, or chemical manufacturers who dive into acylation or targeted alkylation reactions, this compound regularly pops up as a practical choice over other methyl acetamide derivatives or haloacetamides.
Studying chemical synthesis, it’s easy to breeze past the subtle, often invisible details in compound selection—yet it’s these details that play out over time in cleaner results and smoother workflows. For example, 2-Bromo-N-Methylacetamide offers more reliable selectivity in coupling reactions than methylacetamide or its chloro analog. The bromine atom adds reactivity without creating as much unwanted side reactivity as iodine can, and this shows up in higher yields and less troubleshooting during scale-up.
Many folks in pharma laboratories lean toward 2-Bromo-N-Methylacetamide because the molecule allows gentle introduction of acyl or alkyl groups onto more challenging substrates. Compare that to 2-chloro-N-methylacetamide—there, the chlorine might not provide the same balance of activity and manageability in handling. You’ll notice fewer byproducts with the bromo version, so purification steps don’t drag out the process or chew through resources.
Chemistry isn’t just about formulas—it’s the sum of routines, headaches, and those moments when something simply works better. 2-Bromo-N-Methylacetamide often becomes the backbone of selective alkylation steps, especially where researchers focus on introducing methylacetamide groups onto nitrogen or oxygen atoms inside biomolecules or specialty polymers. For instance, folks working on peptidomimetics use it to anchor bromoacetyl moieties, which makes the rest of their chemical modifications much more predictable.
During my graduate research, routine peptide syntheses led me through stacks of amide coupling agents, haloacetamide intermediates, and related N-protected species. Pure 2-Bromo-N-Methylacetamide reliably produced higher conversion rates under less forcing conditions. That saved both time and solvent, which didn’t just help the budget—it kept the results reproducible and easier to build on for the next researcher.
On paper, the melting point usually hovers around 44-46°C. The purity, often greater than 98%, tends to match or exceed other acyl halides used in sensitive syntheses. Labs appreciate the manageable volatility and the fact that it doesn’t degrade as quickly as more reactive iodoacetamide cousins. I’ve tested lots stocked from various suppliers, and keeping it in a cool, dry vial generally means you’ll open a bottle of white to off-white crystals, with no need to rush usage before quality slips.
Some chemists compare N-methyl derivatives and spot the stability difference right out of the bottle. In one project, we transitioned from 2-chloro-N-methylacetamide to the bromo version as a way to fix low coupling rates in a solid-phase peptide synthesis. Reaction monitoring by HPLC showed much crisper peaks and higher integration—showing that a minor change in the leaving group on the acyl moiety made a measurable difference. These day-to-day observations often shape long-term choices in what gets standard shelf space in a lab.
Choosing which acylating agent to stock can set the tone for entire workflows. 2-Bromo-N-Methylacetamide wins out against similar methyl acetamides by offering a strong electrophile while holding back the overzealous byproduct formation that can tank a reaction mixture. Chlorine-bearing analogs sometimes bring lower yields, and iodine’s cost and instability can create unnecessary headaches, especially if you run larger batches or repeat reactions.
As for handling, 2-Bromo-N-Methylacetamide behaves with more predictability during both storage and reaction setup. Other haloacetamides—especially those with two halogens or bulkier N-alkyl groups—lose out due to harsher reactivity or faster decomposition. There’s value in recognizing this difference: you can plan a week’s workflow or scale a small reaction without worrying that product loss or reaction stalling will grind everything to a halt.
Lab safety can make or break any experiment. 2-Bromo-N-Methylacetamide, while still a haloacetamide, sits in a middle ground for risk. Reasonable ventilation, gloves, and eye protection keep risks under control during weighing and transfer. Any direct skin contact causes irritation, and ingestion or inhalation remains a classic chemical safety concern. For teams used to handling acyl halides, this product won’t bring many surprises, but caution always wins out over convenience.
Solid samples rarely cloud the bench or create lingering fumes, but if you’re heating this in open vessels or solvents with low flash points, always work in a fume hood. Over the years, smart workflow has meant using closed vials, weighing boats, and digital balances that won’t trap dust. Once, a small spill during a hurried setup led to minor dermatitis; the experience hammered home the edge gained by setting up proper storage and easy access to cleanup supplies.
Watching trends in organic synthesis, people gravitate toward reagents that stay reliable under pressure. 2-Bromo-N-Methylacetamide appeals to both academic researchers and process engineers looking for higher selectivity in key steps of active pharmaceutical ingredient manufacture. Projects focused on peptidomimetics, specialty monomers, or modified polysaccharides lean toward reagents like this one, because reproducible performance frees up mental energy that would otherwise get lost to troubleshooting.
For many startups and established companies focused on targeted drug development, this product doesn’t just fill a niche—it creates new pathways where previous halogenated amide options dropped short. Colleagues of mine working on proprietary linker technology have relied on brominated acylamides to establish robust connections between molecular cores, branching units, or surface groups. The fine-tuning enabled by the bromo group would show up right away in the analytic data, leaving less cleanup or rework.
Environmental impact should always sit at the front of the conversation, especially for any halogenated reagent. 2-Bromo-N-Methylacetamide, being a single-use reagent for most transformations, doesn’t see much post-processing waste, but the run-off or residual halides still deserve attention. Most of the waste can be neutralized through standard lab protocols, using sodium thiosulfate or similar agents. The key: proper disposal, effective record-keeping, and making sure purchasing volumes match actual lab needs.
Recent years have seen improvements in purification and greener sourcing for bromine-based organics. The benefit for the end user: more reliable inventory, less batch-to-batch variation, and suppliers that back up claims with certificates of analysis. Several procurement professionals I’ve liaised with over time have flagged shortages in less common methylacetamide derivatives, but routine stock checks on 2-Bromo-N-Methylacetamide show steady availability through established specialty suppliers.
Budgets always force tough choices in lab supply lists. Over time, as large-scale manufacturers began securing regular lots, the cost of 2-Bromo-N-Methylacetamide stabilized, making it accessible for smaller research organizations and university groups. Unlike some perishable or exotic intermediates, sealed containers keep this compound shelf-stable long enough for both frequent and occasional users to plan ahead.
I’ve compared quoting cycles for a year’s worth of reagents, and this bromoacetamide variant gives the most bang for the buck in terms of performance versus cost per gram. Compare that to reagents with more niche use-cases or extra stabilization needs, and 2-Bromo-N-Methylacetamide offers space for flexibility that often gets overlooked in tight budgets.
Real progress in the lab comes from the day-to-day moments—those breakthrough mornings when a reaction finally works, or those hard lessons learned from failed runs. In multi-step syntheses involving peptide analogs, colleagues and I tried both bromo- and chloroacetamides side by side, aiming to lock down coupling steps that had drifted off-patent in the pharmaceutical literature. The bromo variant gave cleaner southern blot outcomes and tighter mass spec validation.
Another round of troubleshooting involved an attempted macrolactamization that kept stalling at the coupling stage with the chloro derivative. Only after switching to 2-Bromo-N-Methylacetamide did we see consistent ring closure and isolable product. It felt like a reminder not to underestimate “small” structural changes—one halogen swap can spell weeks saved in a crowded lab calendar.
Bench chemistry relies heavily on being able to reproduce results. One of the biggest frustrations can be working up an experiment that fizzles, not because the mechanism was wrong, but because the reagents didn’t perform to expectation. In that sense, 2-Bromo-N-Methylacetamide builds confidence. In a training setting for junior researchers, giving them access to a reagent with predictable outcomes teaches positive lab habits and builds data sets that hold up during peer review.
Documenting reaction runs using 2-Bromo-N-Methylacetamide regularly leads to narrower error bars and repeatable yields. That might not sound exciting, but anyone who’s lost weeks chasing unknown impurities learns to appreciate this. A big part of informed scientific discovery is knowing exactly what goes into a flask—and why those decisions matter for productivity and credibility.
Every few years, the tides shift in synthetic organic chemistry. As new drug candidates or functional materials hit the literature, the reagents behind those achievements help set standards for the next wave of tools. 2-Bromo-N-Methylacetamide finds itself plugged into many protocols that didn’t exist a decade ago. Looking back, I see how many exploratory syntheses skipped this option—often because the benefits weren’t obvious, or suppliers weren’t keeping up with demand.
In recent discussions around “greener” workflows, peers increasingly ask which acyl halides or amide derivatives give both environmental and economic payoffs. Using fewer auxiliary reagents, producing less halogenated waste, and offering easy handling make a strong case for bromoacetamides over older, bulkier compounds. As a result, future improvements in both synthesis and waste management likely rest in part on the habits and feedback of users in academic and industrial settings.
No compound covers every need. For users scaling up beyond milligram to kilogram batches, better process safety and waste management matter more than theoretical advantages sketched in a literature review. Even small mishaps magnify as the vessel size grows, so the reputation for cleaner, more predictable outcomes becomes much more than a convenience; it becomes risk management in real time.
Troubleshooting slower reactivity or inconsistent product purity sometimes comes down to the solvent or mixing approach. In my time troubleshooting amid shifting project priorities, switching solvents or varying temperature profiles with 2-Bromo-N-Methylacetamide often unlocked better reproducibility. Rather than switching away from the compound, adjusting supporting conditions improved outcomes. Communicating these practical lessons helps research groups avoid starting from scratch or falling into familiar traps with acyl halide chemistry.
Across hundreds of reactions, projects, and long conversations in lab offices, the most persistent conclusion is that process matters as much as the molecule. Choosing a reagent like 2-Bromo-N-Methylacetamide isn’t just about matching a literature procedure; it’s making a judgment about stability, safety, and the long-term reliability of the benchwork. It’s the difference between constant workarounds and a clear, manageable path from starting material to final product.
My experience, and the stories shared by countless collaborators, continues to reinforce the same lesson—compounds like this succeed not just on theory but on day-after-day performance in real, sometimes messy, lab conditions. New graduate researchers, startup teams, and production chemists all benefit when a product bridges the gap between textbook reactivity and everyday usability. The next time someone’s workflow hits a snag with older amide derivatives, 2-Bromo-N-Methylacetamide deserves a closer look, not just for the chemistry, but for the problem-solving it can unlock.