1,10-Dibromodecane: A Down-to-Earth Look at a Versatile Chemical
Historical Development
People started paying attention to long-chain dibromoalkanes, like 1,10-dibromodecane, in the push for more effective intermediates in organic synthesis during the mid-20th century. Chemists in labs and industry both kept searching for ways to connect and extend carbon skeletons, especially with functional groups that offer more than just passivity. The story of 1,10-dibromodecane follows the wider adoption of halogenated hydrocarbons for their reactivity, especially as cross-linkers and in the early polymer and surfactant industry booms. I remember a mentor of mine sharing how early batches sometimes included unpredictable byproducts before process controls tightened up. Once refining practices matured, the product became more reliable, feeding directly into a wider range of industrial and research needs.
Product Overview
1,10-Dibromodecane stands out as a straight-chain dibromoalkane, where bromine atoms cap both ends of a ten-carbon chain. Formulators and chemists value its structure, which balances flexibility with sufficient molecular heft for building more advanced compounds. In practical settings, folks use this material to bridge, extend, and functionalize, leveraging the terminal bromines for substitution or coupling reactions. I’ve seen it used and talked about in project meetings across materials science, where predictable chain length and reactivity make life easier for technical teams.
Physical & Chemical Properties
This compound shows up as a colorless to pale yellow oily liquid, with a faint sweet or halogenated odor. Its molecular formula reads C10H20Br2, and its molar mass sits around 323.08 g/mol. The boiling point typically falls between 320-325°C, though lab folks prefer to work under reduced pressure to limit decomposition. It tends not to dissolve in water, but organic solvents like chloroform, ether, or benzene will do the trick. Stability stands out as a practical advantage, as long as storage skips strong bases, acids, or oxidizing agents. The density, up near 1.4 g/cm³, and its relatively high refractive index make it easy to track in mixtures. From personal experience, it poses handling challenges only if you neglect gloves—it permeates skin fairly quickly.
Technical Specifications & Labeling
Commercial shipments of 1,10-dibromodecane usually guarantee around 98-99% purity, with max limits on 1-bromodecane and decane impurities. People working in procurement often request certificates of analysis with spectroscopic or chromatographic signatures for peace of mind. Typical containers range from amber glass bottles for research labs to steel drums with polyethylene linings for large-scale buyers. Labeling walks a fine line: hazard warnings about skin, eye, and environmental risk, UN identification numbers (UN 2810, Toxic Liquid, Organic, N.O.S.), and all the usual hazard pictograms. Consistency and accuracy on the safety sheets often spell the difference between smooth audits and regulatory headaches.
Preparation Method
Most producers start with decane-1,10-diol, aiming for high-purity raw materials. The diol reacts with phosphorus tribromide or thionyl bromide under controlled, moisture-free conditions, spinning off hydrogen bromide and water as byproducts. Keeping the reaction cold and anhydrous reduces tar formation and helps limit partial bromination. I’ve toured plants where private circuits recapture excess bromide and scrub off gases, with solvent recovery tacked on at every step. Post-reaction, distillation pulls off low-boiling impurities, and final product gets dried, filtered, and packed with desiccant. It takes attention to detail and solid equipment maintenance to hit high yields without introducing color or odor problems.
Chemical Reactions & Modifications
The real draw of 1,10-dibromodecane comes from those two terminal bromines. Each one serves as a launching point for nucleophilic substitution, which turns this molecule into the backbone of all kinds of longer constructs. React it with alkoxides, and you’ll spawn ethers; use it with amines, you’ll shape diamines; match with cyano groups, and you wind up with dicyano derivatives. Chemists in surfactant, polymer, and pharmaceutical groups know how easily it participates in step-growth polymerizations or charges up for macrocyclic ring formation. In research, I’ve watched colleagues stretch its uses toward dendrimers, hydrophobic spacers, and even new sensors that embed halide-responsive elements. Everyone values how this simple skeleton adapts to new functional landscapes with minimal fuss.
Synonyms & Product Names
You’ll hear 1,10-dibromodecane called decamethylene dibromide in older books, alongside 1,10-Dibromodecane, n-Decamethylene dibromide, or 1,10-Bromodecane. CAS: 4109-56-0 usually guides purchasing agents to the right spot. Product brochures from specialty suppliers sometimes tout it as a “decanediyl dibromide” if they’re aiming for the organic synthesis crowd. Regional distributors stick to English or simple translations to avoid confusion in shipping and customs. Experience tells me that cross-checking trade names and chemical abstracts numbers keeps delays off your plate.
Safety & Operational Standards
Anyone who has handled 1,10-dibromodecane knows to respect the risks. Skin contact draws irritation or even sensitization with consistent exposure, and the compound ranks as moderately toxic by inhalation and ingestion. In tight labs and high-volume plants alike, ventilation matters: vapor accumulation combines with heat and static risks to elevate fire hazard. Safety data sheets demand long gloves, face shields, and fume hoods. Waste gets segregated and neutralized using best practice guidelines—alkaline hydrolysis works for cleaning glassware, while incineration (with scrubbing) cleans up bulk spills. Training new staff requires running through hands-on practice, not just paperwork. I’ve seen folks skip basic PPE and pay for it with rashes or headaches—cutting corners just makes more work later.
Application Area
1,10-Dibromodecane’s reach stretches across surfactant synthesis, cross-linking agents for specialty polymers, and rare but important links in the pharmaceutical supply chain. Some manufacturers use it to space apart functional motifs in advanced materials that need both flexibility and insulation. Research teams rely on dibromoalkanes to assemble crown ethers, rotaxanes, or other molecular machines. In the classroom, instructors use it for teaching nucleophilic substitution via hands-on labs. My own projects have seen it serve as a linker for pre-polymers used in adhesive R&D, offering a neat solution for tuning network properties without extra steps. Real-world users appreciate the reliability and straightforward reactivity.
Research & Development
Innovation keeps finding new roles for 1,10-dibromodecane, especially in the realm of advanced polymer electrolytes, functionalized nanoparticles, and engineered sensors. Recent papers keep documenting creative applications in supramolecular chemistry, where researchers stitch together complex architectures with remarkable precision. Scientists playing with dynamic covalent chemistry like using the predictable reactivity to build modular blocks that can rearrange under mild conditions. Industry partners see value in developing “green” or solvent-saving approaches to production, minimizing waste and boosting atom efficiency. At trade shows, I’ve chatted with developers turning to this old staple for new-age tasks, proving that a reliable molecule stays relevant as context shifts.
Toxicity Research
Toxicologists have studied the acute and chronic effects of 1,10-dibromodecane, citing moderate oral and dermal toxicity in rodent models. Prolonged exposure sometimes links to liver or kidney stress, which prompts regulators and users to set conservative occupational exposure limits. Environmental release draws special attention: as a halogenated hydrocarbon, it lingers and can accumulate. Regulatory agencies recommend effluent monitoring and proper destruction. Newer studies in biomonitoring and fate analysis focus on identifying metabolic breakdown products, aiming to clarify risk profiles and shape safer handling protocols. My old advisor liked saying: “Treat every brominated hydrocarbon like it will be on the water report,” which resonates every time disposal paperwork comes around.
Future Prospects
Looking forward, 1,10-dibromodecane seems set for more roles in the synthesis of custom macromolecules, functionalized surfaces, and smart materials. Trends in sustainable chemistry drive a push for greener synthesis routes, perhaps using biobased precursors or milder bromination processes. As electronic materials and medical polymers get more sophisticated, demand for well-behaved spacers and linkers grows. Some startups explore using this compound in novel electrolytes or for surface modifications to control adhesion or biocompatibility. From hallway conversations at conferences, I sense that any molecule with clean, reliable reactions and well-charted safety data won’t fade anytime soon—especially as researchers keep dreaming up inventions that need flexible carbon chains and reactive termini.
How 1,10-Dibromodecane Shows Up in Chemistry
One of the first lessons I learned in the lab is never underestimate how a small change in a molecule can lead to entirely new applications or risks. 1,10-Dibromodecane brings this out quite clearly. Its formula is C10H20Br2. In simple terms, this means the decane backbone carries two bromine atoms, and these sit at the far ends of a ten-carbon chain.
Why Its Formula Matters Beyond the Textbook
In my time working on polymer synthesis, a molecule like 1,10-dibromodecane acts almost like a molecular pair of pliers—reactive ends ready to grab onto something bigger. 1,10-dibromodecane serves as a useful building block in organic synthesis and the polymer world because those two bromine atoms help chemists swap the bromine for other groups, leading to long-chain molecules and new materials. The exact number of carbons and hydrogens between the bromines impacts how flexible the resulting product becomes. For scientists sketching out their routes to make complex molecules, knowing it’s C10H20Br2 is crucial—you can plan out reactions with precision.
The Risks Lurking in Simple Formulas
It’s easy to breeze past a plain formula like C10H20Br2 and forget the chemical can be both useful and risky. If you’ve ever opened a bottle of a dibromoalkane, you remember that sharp, almost stinging odor. The fumes can irritate your lungs or eyes. Too much exposure, and you’re looking at neurological effects, or even cancer risks, since brominated compounds sometimes break down into toxic byproducts. Regulations in most countries call for gloves, fume hoods, and specialized waste protocols balancing the scale between usefulness and harm.
What People Often Miss About 1,10-Dibromodecane’s Profile
Folks outside manufacturing don’t always see how much 1,10-dibromodecane shows up in electronics or pharmaceuticals. Those terminal bromines help researchers attach wires onto carbon chains for sensors or tweak active molecules for drugs. Demand keeps growing as industries tap new uses. Even so, you don’t want spills or careless storage. Brominated decanes travel through soil and water more slowly than light molecules, which means contamination lingers and spreads. Years ago, I was on a clean-up team faced with a persistent spill—no one wants to see something seemingly so plain hang around in the water table for decades.
Safer Chemistry and Smart Choices Ahead
Sticking a bromine atom on each end of decane unlocks a host of possibilities for research and manufacturing. You also step into an area where safety processes and innovation go hand-in-hand. Chemists keep searching for ways to build similar compounds with easier breakdown in nature, using bio-based feedstocks or greener synthesis steps. It matters because every bottle of C10H20Br2 in a storeroom reflects both the progress and the caution necessary in chemical industry work.
Where 1,10-Dibromodecane Finds Its Purpose
1,10-Dibromodecane stands out as a versatile building block for many chemical processes. Think of the standard chemistry lab or industrial setup: folks working with this compound usually seek to create longer carbon chains, often bridging two pieces of a puzzle in organic synthesis. I’ve found the most compelling application surfaces during the making of specialty polymers. Companies aiming to tailor-make plastics with a set degree of flexibility or strength count on these types of dibromoalkanes. Thanks to its ten-carbon backbone, 1,10-Dibromodecane adds real distance between two ends, a quality not all reagents can offer.
Making New Materials Possible
In research circles, people experiment with 1,10-Dibromodecane to synthesize new surfactants. Picture detergents or emulsifiers that keep oil and water mixed. Chemists often need a molecule that can hold two different chemical groups far apart—this is where a ten-carbon chain with reactive ends comes up. My own experience with surface-active agents showed me just how sensitive these materials are to the length of the chain connecting their key groups. In university labs, students learn quickly that switching from a short to a long dibromoalkane doesn't just change the recipe; it changes how the final material behaves.
Building Blocks for Pharmaceutical Intermediates
Drug discovery runs on creativity, and medicinal chemists like to test all sorts of carbon structures to see which one sticks. As soon as a research lab needs a straight, medium-length chain to bring two bioactive fragments together, 1,10-Dibromodecane can show up on the workbench. Through simple substitution reactions, this compound helps scientists stitch together molecules that might fight off bacteria or help treat chronic diseases. It’s never the headline ingredient—more the quiet assistant helping complex structures come together.
Role in Materials Science and Nanotechnology
On the cutting edge, 1,10-Dibromodecane connects up with metallic particles in nanoscience. Specialists want molecules that serve as spacers, holding gold or silver nanoparticles just the right distance apart. It’s a delicate dance—space things out too little or too much, and the whole system falters. In these applications, 1,10-Dibromodecane’s precise chain length makes it more than a generic chemical; it becomes a ruler for the nano-world. Studies published in respected journals highlight this molecule’s contribution to the stability of particle assemblies, influencing things like light transmission or electrical properties in tiny devices.
Potential Hazards and Ideas for Safer Handling
Any chemical as versatile as 1,10-Dibromodecane deserves respect in the lab. Its reactivity—so valuable in synthesis—means eyes and skin need protection. Bromine-containing compounds often carry health risks; direct contact brings danger, and vapors affect breathing. In my own work, using a fume hood and gloves was a straightforward way to control these risks. Regulators from around the globe set limits for worker exposure to such substances. It makes sense to follow their lead by upgrading ventilation or developing less toxic alternatives that perform the same job. Smart solvents and automation also help reduce risk, giving chemists a way to reap the benefits of 1,10-Dibromodecane without unnecessary exposure.
Toward Greener Chemistry
As sustainability moves up the agenda, attention shifts toward using fewer halogenated compounds. Some research teams focus on biodegradable or less persistent alternatives. Green chemistry guidelines encourage limiting bromine releases in wastewater or exhaust, and modern synthesis routes often recycle reagents or convert waste into safer byproducts. Seeing this shift on the ground—swapping out legacy chemicals for greener counterparts—shows the industry is listening. It takes cooperation between chemists, regulators, and manufacturers to strike a balance between innovation and safety.
Understanding the Basics
Brominated hydrocarbons pop up everywhere, from chemical research labs to the making of specialty materials. Among them, 1,10-Dibromodecane stands out thanks to its clear, oily look and the two bromine atoms placed on either end of a ten-carbon chain. This chemical doesn't turn heads on the shop shelf, but a closer look at its physical numbers reveals its real-world value—and its limits.
Boiling Point: A Matter of Handling
Within the realm of organic liquids, 1,10-Dibromodecane maintains a respectable boiling point of about 340°C (644°F). Once, working late in an undergraduate lab, I watched a technician fuss over an overheated flask, sweat beading as he grappled with a much lower-boiling, volatile bromide. With 1,10-Dibromodecane, that kind of stress eases off a bit. Its high boiling point keeps accidental vapor escape in check under normal lab or industrial conditions. No one fancies a surprise puff of dense, irritant clouds, and here, this molecule’s heavy boiling keeps things more predictable when distilling or purifying. This also means higher temperatures to separate or decompose it—something to keep in mind for waste processing or recycling.
Melting Point: How Storage Is Affected
The melting point for 1,10-Dibromodecane falls around 17°C (about 62.6°F). The shift from solid to liquid hovers close to what you’d find in some indoor storage rooms, especially during a cold snap in winter or inside older buildings. My own experience with a similarly melting compound ended in a storage mishap. Without steady temperature control, a once-solid sample pooled into the bottle base, changing how it could be weighed or transferred. This is no minor detail. Planning for storage and shipment needs a close eye on the thermometer, especially if precise portioning matters.
Density: Heftier Than Water
Many people imagine organic liquids floating or mixing readily with water, but bromine’s heft changes the game. 1,10-Dibromodecane weighs in with a density of about 1.46 g/cm³ at room temperature—much heavier than water’s 1.0 g/cm³. Dripping just a milliliter into an aqueous wash, you’ll watch it sink fast, forming a thick layer that complicates clean separation. I’ve spent long afternoons draining separation funnels, cursing small mistakes. Catching the whole lot means keeping pace with its speed and paying attention to drainage, especially in larger wash cycles or when processing waste mixtures. Density also affects volume calculations—shipping by the barrel, you’re packing more pounds into each drum than the same space of water or other light organics.
Why Physical Properties Matter in Real Use
People often overlook boiling point, melting point, and density as trivia—just filler on a safety data sheet. The truth is, these numbers shape nearly every stage of a chemical’s life: how you move it, store it, use it, and clean up after. Boiling point speaks to safety and choice of equipment. Melting point controls how easy it is to dose out or process. Density changes how it handles in blending, dilution, or separation tanks. In research and small manufacturing, this means matching conditions and tools to keep everything running smoothly.
Managing the Challenges
Storage calls for temperature monitoring and insulated spaces, especially in colder climates. Pump systems get chosen to handle liquids that can be thick but mobile at room temperature. Waste streams with heavy bromides need focused separation so nothing slips through into water or soil. Training lab and plant staff on these properties stops small headaches from turning into big environmental or safety mistakes. The numbers aren’t just stats; they’re practical signals to build safer and smoother chemical operations.
Respecting the Risks
Workplaces that deal with organic bromine compounds like 1,10-Dibromodecane don’t run on trust alone. The chemical’s use ranges from lab research to industrial synthesis, and its dual bromine content means it’s not something you’d want spilled on your skin or splashed near your eyes. I’ve learned over years in research environments: never take a clear, oily liquid at face value, especially with halogens in its structure.
Personal Protective Equipment Makes a Difference
PPE lines your first defense. Time and again, gloves rated for chemical resistance, splash goggles, and lab coats prove their worth. Nitrile gloves work well here; latex just doesn’t stand up as firmly to this sort of compound. If there’s a risk of splash or a poorly ventilated area, adding a face shield and a fitted respirator (with organic vapor cartridges) makes even more sense. No one wants to risk bromine exposure, even trace amounts, to the lungs.
Ventilation and Air Quality
Fume hoods aren’t optional where heavier organobromides show up. Ventilation keeps vapors out of your face and off your clothes. I’ve stood in rooms where a stuffy air system let solvents stick around; the difference a working exhaust makes is huge for air quality. Standard fans just recirculate problem compounds, so ducted hoods with outside vent are a must if the work isn’t happening at a small scale.
Spill Control and Waste
I’ve seen colleagues rush when cleaning up a spill. The better approach: slow down, let absorbent pads or vermiculite soak up the liquid, then scoop with dedicated tools. Improper disposal means a visit from the environmental health team and usually a stern warning. Containers marked for halogenated waste aren’t just a formality—halogens interact differently with treatment systems and must not be mixed with regular organic or aqueous waste. We owe it to the next person working in that space to double-check labels and stick to protocols.
Training Matters—Every Time
Refresher training often feels repetitive, but I’ve watched even seasoned chemists make mistakes in the moment. Reviewing proper handling, storage, and emergency protocols actually cuts down on accidents. If your team can’t answer what to do for a skin contact or a splash in the eyes, the risk rises. Running quick drills or walking through SDS sheets as a group ensures everyone stays on the same page, especially with less familiar chemicals.
Storage and Labeling—Staying Organized
Chemicals that look alike can end up misused if proper labels are missing or fading. Color-coded tape or printouts make it clear what’s inside, along with hazard warnings. I always push for keeping these compounds on lower shelves, far from heat sources and strong oxidizers. Locked cabinets with spill trays offer another layer of insurance, especially if shared spaces or mixed-use labs are the norm.
A Healthier Attitude Toward Safety
Treating materials like 1,10-Dibromodecane responsibly sends a signal—one person’s shortcut could be someone else’s health problem later. Stories travel fast in lab circles; I remember hearing about a single glove tear that led to a major incident and weeks of paperwork. Building good habits keeps that history from repeating. In practice, making safety second-nature not only protects everyone but sets a professional standard others follow.
Understanding the Risks Involved
1,10-Dibromodecane sounds pretty technical, but in my own work in basic lab environments, I learned early on that chemicals with halogens such as bromine deserve respect. Any organic compound with bromine tends to have strong effects on the body and the environment. This particular chemical, used in synthesis and specialized chemical reactions, isn’t something you want to leave sitting around your workspace or toss out like expired milk.
Storage: Getting the Basics Right Matters
My first chemistry professor hammered home the lesson: choose your storage spot as carefully as you’d pick a babysitter for your kids. For 1,10-Dibromodecane, that means a cool and dry spot—no sunlight, no moisture, no random hot pipes running past. High temperatures can speed up decomposition, and light exposure might set off unwanted reactions, especially over time. Every lab I worked in kept brominated compounds in tightly sealed glass containers, and usually in a secondary containment tray. This helps stop leaks from spreading and adds a layer of backup in case something goes wrong.
Labels matter. The number of times I’ve seen brown glass bottles with faded handwriting… it’s more than I care to remember. Clear, fresh labels with chemical names and hazard information save time and, sometimes, lives. Storing this chemical far away from strong oxidizers and open flames lines up with almost every safety manual out there. Brominated organics burn with toxic fumes, and you really don’t want to find out just how bad that can get.
Personal Safety: Barrier Between You and the Chemical
My skin still tingles from a minor solvent spill years ago. Gloves, lab coats, and goggles give peace of mind. Crack a window or run a fume hood if you’re moving or decanting 1,10-Dibromodecane. Inhaling bromine vapors can irritate airways, and even small exposures can build up over time. PPE isn’t for show—it protects your long-term health.
Disposal: Doing the Right Thing Takes Extra Steps
Dumping chemicals down the sink sounds easy, but I’ve seen what it does to drainage pipes and, more importantly, rivers. 1,10-Dibromodecane counts as hazardous waste under environmental safety rules because bromine compounds can stick around, poisoning aquatic life and entering the food web. Most municipalities ban regular trash or drain disposal for these chemicals.
At every lab I’ve worked in, waste gets containerized as soon as it’s made. Dedicated hazardous waste bins—clearly marked and with airtight lids—avoid cross-contamination. Regular pickups from licensed chemical waste handlers solve the problem at scale. It costs money, but dumping costs everyone much more in the long run.
Better Habits, Safer Workplaces
Colleagues who treat chemicals with the same care they’d give a chainsaw make workplaces safer. Regular refresher courses and real conversations about close calls build trust and keep the culture strong. If you’re unsure whether you’re storing or disposing of something safely, local environmental health offices give practical guidance. Relying on facts, not shortcuts, means fewer accidents and cleaner communities.
| Names | |
| Preferred IUPAC name | 1,10-dibromodecane |
| Other names |
Decamethylene bromide
Decylene dibromide |
| Pronunciation | /ˈwʌnˌtɛn daɪˌbroʊmoʊˈdɛkeɪn/ |
| Identifiers | |
| CAS Number | 4109-56-0 |
| Beilstein Reference | 703080 |
| ChEBI | CHEBI:38699 |
| ChEMBL | CHEMBL227143 |
| ChemSpider | 12714 |
| DrugBank | DB08373 |
| ECHA InfoCard | 03dd7900-f878-3bce-b7a5-b0d8dd2d2b8f |
| EC Number | 203-899-6 |
| Gmelin Reference | 78587 |
| KEGG | C19068 |
| MeSH | D000319 |
| PubChem CID | 80817 |
| RTECS number | KI4025000 |
| UNII | 6D7V7M448B |
| UN number | UN1993 |
| CompTox Dashboard (EPA) | DTXSID7020373 |
| Properties | |
| Chemical formula | C10H20Br2 |
| Molar mass | 391.08 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Odor | Odorless |
| Density | 1.368 g/mL |
| Solubility in water | Insoluble in water |
| log P | 5.61 |
| Vapor pressure | 0.00019 mmHg (25 °C) |
| Acidity (pKa) | 14.0 |
| Magnetic susceptibility (χ) | -8.64e-6 cm³/mol |
| Refractive index (nD) | 1.50400 |
| Viscosity | 3.47 cP (25°C) |
| Dipole moment | 2.48 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 589.9 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -44.9 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -6298.7 kJ/mol |
| Hazards | |
| GHS labelling | GHS02, GHS07 |
| Pictograms | GHS07 |
| Signal word | Warning |
| Hazard statements | H315, H319, H411 |
| Precautionary statements | P210, P273, P280, P301+P312, P305+P351+P338 |
| Flash point | > 132 °C |
| Explosive limits | Explosive limits: 0.9–6.5% |
| Lethal dose or concentration | LD50 oral rat 5050 mg/kg |
| LD50 (median dose) | LD50 (median dose): >5 g/kg (rat, oral) |
| PEL (Permissible) | Not established |
| REL (Recommended) | 50 mg |
| IDLH (Immediate danger) | Not established |
| Related compounds | |
| Related compounds |
1,10-Diiododecane
1,10-Dichlorodecane 1,10-Dodecanediol Decane 1-Bromodecane |
