|
HS Code |
133563 |
| Iupac Name | 1-(2-bromoethyl)-4-methylbenzene |
| Molecular Formula | C9H11Br |
| Molecular Weight | 199.09 g/mol |
| Cas Number | 3663-55-0 |
| Appearance | Colorless to pale yellow liquid |
| Boiling Point | 243-245°C |
| Density | 1.34 g/cm³ |
| Melting Point | -10°C |
| Refractive Index | 1.548 |
| Flash Point | 110°C |
| Solubility In Water | Insoluble |
| Smiles | CC1=CC=C(C=C1)CCBr |
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Progress in chemical synthesis often depends on the reliability and versatility of the building blocks we use. 1-(2-Bromo-Ethyl)-4-Methylbenzene, sometimes known in labs by its structural features, stands out with its distinctive combination of a bromoethyl side chain and a methyl group attached to a benzene ring. While many aromatic compounds flood the market today, this particular structure invites deeper consideration for both its practical uses and its clear, traceable origin within the chemical literature.
The world of aromatic derivatives is anything but flat. Add a bromoethyl group to a toluene backbone and you get a molecule that keeps showing up in innovative syntheses and carefully designed research. As someone who’s worked in organic synthesis, I’ve relied on intermediates like this one in multiple projects, not because catalogues suggest them, but because their reactivity proves valuable on the bench, time and again.
You know that purity isn’t just a selling point; it determines how clean your reactions run, how straightforward your purifications go, and whether you waste hours trouble-shooting. This product typically arrives as a colorless to pale yellow liquid or sometimes a crystalline solid, depending on storage and temperature. In the lab, familiar hints—like the scent of methylbenzenes—confirm what the label says. As a brominated compound, it should measure up to high expectations:
Some labs might see variability in physical appearance across batches. From experience, this comes down to storage and small process tweaks during purification. Reputable suppliers should track batch quality and support any questioning from a practicing chemist's perspective.
Plenty of halogenated toluenes are out there. Yet, 1-(2-Bromo-Ethyl)-4-Methylbenzene gives chemists a distinctive angle. The bromoethyl side chain isn’t just a decorative flourish. In practical terms, it opens doors for nucleophilic substitution, cross-coupling reactions, and the construction of more complicated organic motifs. Compared to standard para-xylene or “plain” methylbenzene, you pick up reactivity thanks to the bromine atom, especially when targeting primary or secondary amines, ethers, or other substitution targets.
Working with this compound, I found its reactivity more manageable than with primary alkyl bromides, which often overreact or give pesky by-products. The presence of a methyl group at the para position seems subtle, but it actually tames the molecule, lending increased stability during bench manipulations. There’s far less degradation over time compared to less substituted analogues, which cuts down on wasted material and repeat syntheses.
When experimenting in the lab, I noticed that 1-(2-Bromo-Ethyl)-4-Methylbenzene doesn’t produce the persistent odors or volatility issues that crop up with lower molecular weight brominated benzenes. This makes handling more comfortable, especially over hours of reaction setup and column purification.
Over the years, organic chemistry has evolved into a field where modular molecules hold enormous sway. This brominated aromatic serves as a solid building block in several applications:
I’ve seen this molecule gain traction outside classical organic synthesis, too. Some researchers use derivatives as probes for mechanistic investigation, relying on the clean substitution patterns it allows. In personal experience, I’ve found it easy to track through reaction steps as its spectral signatures—particularly in NMR—stay clear and distinctive through multiple transformations. That saves a lot of time during scale-ups or complex multi-step syntheses.
Selection amongst chemical intermediates often feels overwhelming. The market is full of bromoalkyl aromatics, but not all perform the same. Comparing 1-(2-Bromo-Ethyl)-4-Methylbenzene with simpler compounds like benzyl bromide or 1-bromo-4-methylbenzene, a few key points jump out.
Benzyl bromide, for all its popularity, runs the risk of unwanted side reactions due to its higher reactivity. This product sits in a “sweet spot”—reactive enough for most substitutions but less likely to overreact, leading to cleaner downstream chemistry. The side chain in 1-(2-Bromo-Ethyl)-4-Methylbenzene gives chemists more scope: it extends the carbon skeleton for added structure, while the para-methyl group offers extra selectivity or improved compatibility in certain reaction schemes.
This comes in handy during scale-up, too, where batch-to-batch consistency becomes crucial. In the pharmaceutical setting, regulatory bodies look for structural clarity and process repeatability. Aromatic intermediates with well-defined functional groups, like this one, fit those needs much better than “bare” bromoalkyls prone to rearrangement or side reactions. From my discussions with colleagues in industry, these practical points matter just as much as the chemical details—nobody wants a promising route hampered by variable starting materials.
Brominated aromatics demand respect. Exposure to skin or eyes should always be avoided, and working in a ventilated hood is standard procedure. My experience lines up with established advice: this molecule doesn’t volatilize as aggressively as lighter aromatics, but the bromine atom means gloves are non-negotiable. During clean-up, handling small bench spills is straightforward, since trace amounts can be mopped up using neutral absorbents and organic solvent rinses.
Disposal brings up its own issues. Many institutions maintain strict protocols for halogenated waste, and rightly so. Never pour it down the drain. Keep all waste in sealed containers, and label them clearly. Repeated exposure over months or years could present risks, so any team scaling up synthesis ought to review protocols regularly. In my lab, annual retraining and updates on chemical waste provide the baseline for keeping everyone safe. Resources from regulatory publications support these practices, and it pays to stay current.
Picking a chemical compound for serious work means looking beyond just price and purity. I make a point of checking certificates of analysis and inquiring about production standards before settling on a supplier. Consistency from batch to batch matters most for tricky reactions, where minor changes can throw off yields or product qualities. Labs with ISO certification or documented in-house processes almost always provide the kind of reliability I want.
Some questions come up more often than others when sourcing organics: How fresh is the batch? Have impurities been fingerprinted using up-to-date instruments? Detailed NMR and GC analyses should be standard. If I get a COA without this data, I ask for it. Higher-quality sources include chromatograms alongside their paperwork, offering peace of mind for method development or regulated applications.
Life in the lab rarely follows a script. Sometimes a substitution fails, or purification goes awry because of unseen impurities or by-products from unstable reagents. What I appreciate most about 1-(2-Bromo-Ethyl)-4-Methylbenzene is the way it stands up to these challenges. Its relative stability gives it a slight edge during storage—even after months on the shelf, structure and performance stay sharp if stored correctly, away from direct sunlight or high humidity.
When I switch to this molecule from others in the same family, I notice fewer headaches during chromatographic separation. The compound’s aromatic signals stay sharp in NMR and shine through the background noise, even after extended reaction times. Unlike some more obscure intermediates, it doesn’t clog up columns or stick to glassware during washes—a practical consideration for anyone running repeat syntheses or prepping for scale-up.
In research, surprises appear on almost every page of a lab notebook. But the right starting materials cut down on the guesswork. This compound provides a balance: its chemical “handles”—the bromine and the methyl group—help guide reaction selectivity. I’ve seen research teams take bench-scale methods right up to pilot plant stages simply because intermediates like this don’t throw curveballs.
For anyone planning on bigger syntheses, it’s wise to check up on the compound's shelf life in advance. From experience, unopened containers stored in cool, dry cupboards rarely show signs of decomposition after a year. Opened bottles—especially those exposed to repeated cycles of hot and cold—should be used more promptly. Keeping silica gel nearby during storage helps trap stray moisture before it becomes an issue.
Environmental conversations aren’t reserved for policymakers. Chemists working with halogenated organics, such as this one, should remain alert to downstream consequences. Waste management needs more than a standard plan. I push for solvent recovery systems and targeted waste segregation in every workplace I join. My team once switched to micro-scale reactions for preliminary screens, drastically dropping the total volume of halogenated waste each week. Over time, small changes like these add up.
While the world seeks greener alternatives, reality means certain syntheses demand these reliable reagents. The best approach balances immediate research goals with a chain-of-custody mindset, ensuring safe disposal and minimal escape into local water systems. I recommend everyone review local regulations before starting new projects, and never assume even “trace” quantities are harmless outside controlled settings.
What makes a molecule more than its catalog number? A mix of reliability, selective reactivity, and accessibility for those solving real problems, not just writing up papers. I’ve worked on both academic and industrial teams, where the flexibility of intermediates like 1-(2-Bromo-Ethyl)-4-Methylbenzene greases the wheels for everything from medicinal candidates to new polymer backbones.
Chemists entering new fields—say, functional materials or pharmaceuticals—need intermediates that handle predictable substitution while protecting other sensitive groups. The truth is, compromise isn’t always necessary. This molecule shows up repeatedly in published synthetic routes for exactly that reason. Those branching out into process chemistry often find it bridges the gap between affordability and reliability, without demanding new safety gear or exotic handling protocols.
1-(2-Bromo-Ethyl)-4-Methylbenzene markets itself not just by specifications, but by performance. Chemists looking for purity, steady reactivity, and handy spectral signatures will notice a marked difference compared to flimsier analogues. Its position as a flexible aromatic intermediate—useful in both research and industry—reflects years of proven results in synthesis. Care in sourcing and storage ensure repeatable outcomes, while standard chemical safety and waste management protocols maintain a responsible balance between utility and stewardship. Collecting experience and published results together points to this compound as more than a chemical; it’s a genuine facilitator for progress in today’s science-led landscape.