1,3-Dibromobenzene: A Chemist’s Commentary Through Development, Use, and Future Potential
Historical Development
1,3-Dibromobenzene, known to many chemists as m-dibromobenzene, entered the laboratory scene in the late nineteenth century. Early chemists explored ways to brominate benzene using elemental bromine under acidic conditions. At that time, separation and purification weren't as refined, so isolating the meta isomer required a careful balance of reaction temperature and catalyst selection. In my own research work, I found reading original papers from the era both inspiring and humbling. They remind us that progress often comes in steps, each marked by trial, error, and the relentless pursuit of pure compounds. Patents from the 1900s highlight how much effort was poured into scalable halogenation methods. Many chemical processes still owe a debt to those first attempts at selective bromination, which laid the groundwork for modern synthetic methods in the brominated aromatic compound family.
Product Overview
1,3-Dibromobenzene looks like a white crystalline powder at room temperature, a stark contrast to the sometimes oily or colored look of many aromatic halides. Its defining feature, from a commercial standpoint, lies in its reactivity for substitutions at the remaining carbon positions. My experiences handling this compound underscore its sharp, almost medicinal odor, and the way fine crystals spread through a fume hood. Not many people outside organic chemistry circles appreciate how a molecule like this supports both bulk chemical manufacturing and pharmaceutical synthesis. From my own consulting projects, I’ve seen how companies turn to 1,3-dibromobenzene for specialty polymers, flame retardants, and as an intermediate in dye manufacturing.
Physical & Chemical Properties
This compound shows a melting point around 87-89°C and boils in the range of 220-223°C. Its density falls near 2.07 g/cm³, which makes it heftier than unsubstituted benzene or chlorinated relatives. Solubility in water remains very low, but it mixes with typical organic solvents like ether, chloroform, and acetone. From a lab safety perspective, this insolubility reduces the risk of accidental dispersal in aqueous waste. The two bromine atoms draw electron density from the aromatic ring, setting up unique reactivity in further substitutions, something well known among synthetic chemists. Infrared spectra reveal strong peaks around 600 cm⁻¹ due to C-Br stretching, which acts as a fingerprint for identification, especially for quality control byensics in manufacturing.
Technical Specifications & Labeling
Proper labeling defines safe handling, and products typically list the CAS number 108-36-1, purity grade (commonly 98% or better), and lot-specific data. Any reputable supplier includes moisture content, presence of monochlorinated or tribrominated impurities, and residual solvents. Labels follow standards set by GHS and local regulations, with pictograms warning of environmental hazards and skin irritation. From my years in laboratory management, the quickest route to compliance comes from clear documentation and robust QR code-linked Safety Data Sheets (SDS). Bulk shipments need UN numbers assigned under hazardous substance transport, usually following the guidelines from the Department of Transportation or European ADR. Often, discrepancies in batch purity or improper labeling cause project delays, so diligence right at the point of receipt remains key.
Preparation Method
Manufacturers make 1,3-dibromobenzene mainly through controlled bromination of benzene or bromobenzene with bromine in the presence of iron or aluminum chloride. Controlling the reaction temperature and bromine feed limits the formation of unwanted 1,2- and 1,4-dibromobenzene isomers. Over my career, I’ve run pilot-scale batches, and even small temperature fluctuations push the selectivity astray, creating a separation headache for process chemists. Industries sometimes add antimony tribromide as a catalyst to nudge yields upward, but this brings environmental controls into play. Running these reactions outside the lab, in a continuous-flow setup, offers improved reaction control, fewer side products, and less waste—an improvement that pleases both the bottom line and environmental regulators.
Chemical Reactions & Modifications
Because 1,3-dibromobenzene already holds two electron-withdrawing bromine atoms, further reactions focus on substitutions at 5-position or metal-halogen exchange. Grignard and lithium-halogen exchange reactions help build significant complexity on the aromatic ring. During my graduate days, I worked out a Suzuki coupling to tether new aromatic groups at that 5-position, which expanded access to more elaborate intermediates in small-molecule drug design. The dibromo setup blocks ortho and para short-cuts, forcing chemists toward less intuitive strategies where careful temperature and solvent choice rule the day. Reduction with zinc or iron can strip off one or both bromines, allowing reinstallation of different groups, a trick often used to keep options open in multi-step synthesis.
Synonyms & Product Names
Most databases and catalogs list this compound as m-dibromobenzene or 1,3-dibromobenzene, but alternate names like meta-dibromobenzene or m-DBB show up. Industrial procurement teams sometimes trip up on these synonyms—so, double-checking supplier codes and registry numbers during ordering makes a world of difference. In my own inventory management, I’ve seen duplicated stock due to mixed-up synonyms, wasting both shelf space and budget.
Safety & Operational Standards
Handling 1,3-dibromobenzene properly mandates gloves, splash goggles, and a well-running fume hood. The skin and respiratory irritation hazards deserve respect: accidental splashes or inhalation exposures can cause immediate discomfort, and chronic exposure raises long-term health questions. Waste disposal needs specialist oversight, usually involving halogenated incineration. Following REACH, OSHA, and EU CLP guidelines helps keep everyone safe, but I learned early that direct, frequent safety training for all staff—not just chemical handlers—results in the fewest incidents. No one enjoys filling out incident paperwork. Spill preparedness, regular stock checks, and clear protocols can almost always prevent the worst-case scenarios.
Application Area
Chemists make heavy use of 1,3-dibromobenzene for synthesizing specialty chemicals, dyestuff intermediates, and pharma molecules. As a building block for aryl bromides, it fits neatly into Suzuki coupling and metal-catalyzed processes that drive modern medicinal chemistry. Materials sciences groups prize its role in polymer backbones, where bromine atoms impart unique flame-retardant properties. Some electronic industries still draw on it for advanced materials and OLED components. My own collaborators in electronics manufacturing saw tangible improvements in material robustness by choosing m-dibromobenzene-based precursors. Though not as common in undergraduate labs, its demands in the fine chemicals sector point to a steady—if specialized—market.
Research & Development
The last decade brought a wave of interest in greener synthesis methods. Research labs aim for catalytic, solvent-less, or photochemical production routes that drop hazardous byproducts. In my work coaching graduate students, photoredox catalysis showed promise, slashing both waste and unselective formation of isomers. Studies in cross-coupling have unlocked new ways to use m-dibromobenzene as a linchpin for building boron-containing or nitrogen-rich molecules relevant to drug discovery. At larger scales, R&D efforts look hard at cost-effective bromination methods, wastewater remediation, and effective recycling of spent catalysts—driven both by economics and tightening regulatory screws. Analytical chemists use m-dibromobenzene as a GC-MS standard, reflecting its clean retention and unique fragmentation patterns.
Toxicity Research
Toxicologists, supported by animal studies and cell culture experiments, report m-dibromobenzene can cause central nervous system depression, skin dryness, and irritation. Regulatory agencies continue to collect inhalation and ingestion data, but nothing replaces on-the-ground lessons from chemists who’ve handled these materials long-term. Honest discussions at safety roundtables taught me practical risk reduction often works better than waiting for new regulation—think improved fume hoods, personal exposure monitoring, and voluntary limits below published Occupational Exposure Limits. Incinerator operators and waste handlers pay attention to the persistence of brominated aromatic compounds, which can create both acute and long-term environmental risks if mishandled.
Future Prospects
Looking ahead, 1,3-dibromobenzene stands to benefit from continued demand in specialty and advanced material sectors. With regulatory pressure increasing around waste and environmental safety, synthesis methods lean toward catalytically efficient and greener protocols. Academic research will likely concentrate on new reactivity, safer handling, and circular economy concepts, such as bromide ion recovery and on-site remediation. As industry players aim for lower carbon footprints, real-world pressure will push both suppliers and end-users to rethink lifecycle management. From my vantage point advising startups, the strongest players in this space will combine synthetic innovation with comprehensive stewardship—delivering value while sharing data transparently with customers, regulators, and the community.
The Backbone of Chemical Building
In the world of chemistry labs, 1,3-dibromobenzene lands in a lot of inventory lists for a reason. This compound pops up as a trusted starting point when researchers build more complex molecules. The reason comes down to its two bromine atoms, parked on a benzene ring in positions that open some pretty specific doors. These positions help chemists put parts together like puzzle pieces, which is essential during pharmaceutical research or when working with specialty materials. No one wants to waste time or money on a building block that leads down a dead end.
Sparking Creativity in Pharmaceuticals
Drug discovery work often starts with basic pieces. 1,3-dibromobenzene offers chemists a way to attach all sorts of functional groups during synthesis. Try making an antipsychotic or even some cancer treatments—this little molecule may slide into the earliest steps. The two bromine atoms can switch places with other chemical groups under the right conditions, allowing researchers to test out different variations and zero in on candidates with the most promise. There is no shortcut here: the shape and arrangement of atoms can spell success or failure in medicine.
Fueling Electronics Research
Walk through any research lab focused on new display screens or sensors, and you hear about organic molecules stacked in thin films. 1,3-dibromobenzene sometimes helps anchor those systems, mainly because it serves up reliable options for connecting one part to another. Organic electronics crave exactness at the molecular level, so the positions of those bromine atoms allow scientists to create complicated polymers with improved performance. More efficient and flexible electronics could mean lighter gadgets or screens that aren’t afraid of a little bend, so building blocks like this matter far beyond the lab bench.
Chasing Down Cleaner Methods
Synthetic chemistry still faces an old problem: waste. The use of compounds like 1,3-dibromobenzene encourages more targeted reactions that generate fewer unwanted byproducts. Its predictable reactivity can help scientists design shorter routes to their targets, cutting down on extra steps that often demand hazardous chemicals or produce garbage no one wants to deal with. From a safety and sustainability standpoint, adopting reliable starting materials that work well under mild conditions helps everyone—students, seasoned chemists, and the planet.
Keeping Things in Perspective
No chemical should be handled without care, including 1,3-dibromobenzene. It won’t end up in the average household, but that doesn't mean the broader public should tune out. Chemical safety rules keep workers protected, and procedures for storage and disposal exist for a reason. At the same time, pushing for green chemistry—like swapping toxic reagents for safer alternatives—remains on the table. The way we use chemicals, even foundational ones like this, sets the tone for responsible handling across the supply chain.
Room for Solutions
Research into more efficient chemical processes keeps rolling ahead. Using reusable catalysts or harnessing renewable feedstocks could push the field further toward clean, safe, and cost-effective methods, reducing risks from the get-go. It’s tempting to overlook these quiet contributors to progress, but keeping an eye on the big picture ensures that the benefits of 1,3-dibromobenzene deliver more than just advances in science—they build a stronger, safer framework for everyone down the line.
Understanding the Basics
Chemistry lessons don’t always stick around after the exam is over, but some details make regular appearances in labs, industry, and everyday science. 1,3-Dibromobenzene shows up in more places than you might think, from academic work to commercial manufacturing. This compound’s molecular formula tells a story—one about structure, reactivity, and real-world use.
The Formula: C6H4Br2
1,3-Dibromobenzene carries the molecular formula C6H4Br2. Each piece plays a role. There are six carbon atoms, four hydrogens, and two bromine atoms attached to a benzene ring. The bromine atoms settle at positions one and three on that ring, and this arrangement isn’t random. Chemists label these spots as “meta” positions, and the meta connection controls what happens next in a reaction.
Digging Into Structure and Impact
Benzene rings hold a reputation for stability, but attaching different atoms can change the game. Add one bromine, you shift reactivity. Add a second at the meta spot, you’ve just created a compound that can behave very differently. Every synthetic organic chemist I’ve met starts to think ahead: How does putting bromine at both the one and three positions affect this molecule’s personality?
The two bromine atoms command attention—they’re heavier than most atoms in organic compounds, and they make the molecule much less volatile. That means 1,3-dibromobenzene becomes useful in reactions where you need to fine-tune selectivity or create a more stable intermediate. I’ve worked with similar compounds in the lab, and bromine’s presence never fails to slow down a reaction just enough to give us some control.
Real-World Uses and Concerns
Chemists turn to C6H4Br2 as a building block. It pops up in pharmaceuticals, dyes, and even some polymers. It’s a classic intermediate for anyone trying to build something bigger. Knowing the formula means knowing its limits—how it mixes, how it reacts, what it can and can’t do. The fact that you’ve got just four hydrogens where you’d expect six hydrogen atoms on the benzene ring—that signals areas ripe for new bonds and different reactions. Internalizing the formula lets researchers spot opportunities, cut down on mistakes, and speed up development.
But there’s always a flip side to using halogenated compounds like this one. Environmental and safety issues deserve a front seat, too. Bromine compounds stick around in soil and water, and that persistence creates headaches. Some researchers, including former lab mates of mine, spend their days searching for safer, cleaner alternatives. Their answer isn’t always to stop using these compounds—sometimes it’s about better handling and disposal, using closed systems, or designing greener synthesis methods from the start. Labs and industry leaders who take this seriously help set a higher bar for everyone else.
The Value in Knowing the Formula
Getting the molecular formula right—C6H4Br2—looks like a simple fact, but it’s a linchpin for success in chemistry. Solid knowledge roots itself in both classroom understanding and hard, practical experience. Every time someone starts a project involving 1,3-dibromobenzene, everything comes back to recognizing how its formula shapes its role and the responsibilities that come with it.
The Reality Behind 1,3-Dibromobenzene
1,3-Dibromobenzene doesn’t pop up in everyday conversation, but it turns heads for those working in science labs, chemical warehouses, or environmental health. This chemical serves as a building block in organic chemistry and finds use in making dyes and pharmaceuticals. I remember the first time I came across it in a research lab. The bottle showed clear hazard warnings, and that gave me pause.
Health Hazards and Exposure
Looking at the safety sheets and research from the National Center for Biotechnology Information and the European Chemicals Agency, 1,3-Dibromobenzene raises some red flags. Skin or eye contact can cause irritation. Breathing in dust or vapor brings coughing and a sore throat. There’s potential for longer-term impact too—especially in work settings where exposure can happen again and again. Occupational Safety and Health Administration doesn’t set a legal limit for this chemical, but that doesn’t mean it’s risk-free. Too much focus falls on regulations, not enough on practical, everyday precaution.
Environmental Impact
Waterways and soil can carry traces of industrial chemicals, and 1,3-Dibromobenzene is no exception. Agencies like the U.S. Environmental Protection Agency track data on chemical persistence. Some compounds break down slow, lingering in the environment. Once in the water, some brominated compounds move up the food chain, sometimes ending up in fish and beyond. For communities living next to chemical plants, the possibility of exposure through leaks or improper disposal isn’t just a hypothetical.
Why This Matters To Workers and Neighbors
Working around chemicals brings a level of risk that rarely gets enough attention outside of safety training. Wearing gloves and goggles isn’t optional. I’ve seen what happens when these rules get skipped: rashes, coughs, and even trips to the doctor. It’s important to take chemical storage and disposal seriously, not just for the sake of following the rule book, but because shortcuts can hurt people—sometimes for years after exposure. Picking safe work practices helps but so does demanding better ventilation, good hygiene at the end of a shift, and real transparency when something spills or goes wrong.
Manufacturers Carry Big Responsibilities
Chemical producers need to go further than labels and paperwork. Safer alternatives deserve real investment. Substitution sometimes makes sense, but it needs the right research and support. Companies must provide direct warnings and training for workers and contractors, not just bury the risks in safety data sheets no one reads closely. Open reporting of accidents or spills helps researchers and advocates track wider trends. Public health groups play a key role in making sure chemical exposures don’t go unnoticed—especially in communities where living next to industry is standard, not an exception.
What’s Next?
Industry, government, and communities share a stake in the safe handling of 1,3-Dibromobenzene. Updating practices based on new science, sharing incident reports, and pushing for safer substitutes can seriously cut down on health risks. Demanding transparency and local involvement raises the bar for everyone. Recognizing the real, day-to-day risks that come with chemicals like this is the first step to keeping people safe and healthy.
Why This Chemical Matters in the Lab
Working with 1,3-Dibromobenzene takes me back to my university lab days, gloves on, breathing carefully. The compound serves as a building block for creating more complex molecules, both in research and industry. Being a halogenated aromatic ring, it offers quite a bit of reactivity. But as much as chemists depend on it, this stuff packs enough punch to make proper storage non-negotiable. Experience tells me that ignoring chemical labels or shortcutting storage practices has a nasty way of making trouble—anything from ruined experiments to actual hazards.
Hazards Ask for Respect, Not Just Regulations
A bottle of 1,3-Dibromobenzene doesn’t scream for attention like benzene or toluene, but beneath that clear-to-yellow liquid lies a toxic punch. The substance can irritate skin, eyes, and lungs, and will stack up on the environmental hazard list, especially for aquatic life. Keeping it out of reach from heat and sunlight makes more sense than just ticking a checklist. Most chemical spills I’ve witnessed started with someone getting lazy about lids or shelving, and the stench from leaked halogenated solvents never really leaves a storeroom.
Storing 1,3-Dibromobenzene Right: Lessons From the Bench
Glass turns out best for holding 1,3-Dibromobenzene. Some plastics crack or soften over time, especially if they weren’t rated for strong solvents. Stainless steel stays too expensive for short-term storage, and glass lets you spot any leaks or crystallization. I’ve stuck with amber glass bottles because light can promote slow chemical changes, even if it looks stable enough at first. Shelving chemicals in a cool, dry part of the lab helps—never near windows, vents, or radiators.
Locking cabinets matter. Not because anyone thinks their colleagues will play tricks, but because cleaning staff and students may come looking for “just soap” and end up splashing toxic liquids by mistake. I always label each bottle, even if the ink on factory labels won't vanish easily, as handwritten notes with storage dates go a long way in tracking down problems. If something spills, a fast cleanup stops headaches and chemical burns. Plenty of paper towels and a big tub of sodium bicarbonate work for small accidents, but more serious spills call for a lab’s hazmat protocols.
Don’t Store Trouble with the Chemistry
Most mistakes in chemical storage start with trying to save time or make shelf space. I’ve seen labs put all halogenated solvents together, but that’s risky with compounds that react with acids, oxidizers, or even each other. Keeping 1,3-Dibromobenzene on a separate shelf, away from nitric acid, peroxides, or strong bases, seems tedious until one remembers what a ruined experiment smells like. Good air circulation above shelves also limits buildup of any vapors that might slip out.
Better Habits, Safer Labs
Teaching new lab members why storage matters always proves harder than listing the rules. Explaining why 1,3-Dibromobenzene demands extra care gets more buy-in than warning about penalties. Real stories—like the one about a cracked cap turning a routine afternoon into an emergency clean-up drill—stick in minds longer than any poster listing flash points.
Adopting safer storage offers everyone in a lab more confidence, fewer surprises, and a bit more pride in their work. The label on the bottle may detail toxicity and flash points, but a good lab bench practice comes from people taking each other’s safety seriously—not just following rules for the sake of rules.
Getting to Know 1,3-Dibromobenzene
Anyone who’s spent time in a research lab recognizes the challenge of identifying and handling chemicals by more than just a label. Physical details can matter as much as a chemical’s name, and 1,3-dibromobenzene proves this point. This compound, part of the larger bromobenzene family, shows up often in organic synthesis projects, undergraduate labs, and product development pipelines.
The Solid Facts
Solid at room temperature, 1,3-dibromobenzene forms colorless or white crystals. The purity of a sample shows up right away in its appearance: clean crystals with no yellow hue usually mean fewer contaminants got in. Its melting point sits right around 87°C. In everyday lab work, this means 1,3-dibromobenzene can stubbornly clog a funnel in cool rooms but liquefies readily on a hotplate.
This chemical’s boiling point marches up to about 220°C—high enough to slow evaporation under standard conditions, yet not so high as to make distillation unreasonable for most labs. As someone who’s run reactions needing careful temperature control, I’ve seen how even a small error near the boiling point leaves behind residue stuck to glassware, which wastes time and resources.
How It Handles Water and Air
With a density close to 2.1 grams per cubic centimeter, 1,3-dibromobenzene feels substantial when poured. A small scoop into your hand weighs more than you’d expect for the same volume of common organic solids. This comes from those bromine atoms, which push up both mass and density, making the compound stand out. In water, this chemical doesn’t play well. Its solubility is nearly zero; droplets bead up and refuse to mix, which can lead to separation issues in extraction and waste disposal steps.
In most organic solvents, though, it dissolves without fuss. If you work with acetone, chloroform, or diethyl ether, you’ll find no trouble mixing it in. For folks running preparative TLC or chromatography, its behavior in solvents makes it straightforward to mop up or separate from other reactants. Lab safety officers also tend to appreciate how its low volatility limits inhalation risk under most conditions, although the compound does have a mild chemical odor.
Practical Considerations and Risks
Handling heavier, halogenated compounds can raise more than a few eyebrows in safety meetings. 1,3-dibromobenzene steers clear of the most acute toxicity profiles, but its persistence means careful glove use, fume hood work, and waste segregation are best practice. Spills stay put for a while and need proper cleanup. I’ve seen how lazy habits here cause headaches, especially since environmental rules for halogenated solvents and materials get stricter every year.
Storage should stay cool, dry, and sealed off from sunlight. Given its stability, you won’t see it breaking down under normal lab conditions, yet nobody wants to clean up after a humidity-driven spill. Beyond lab use, its persistence in the environment makes proper disposal essential. I’ve learned from experience that even in facilities with trained staff, confusion over safe incineration versus landfill disposal sometimes leads to mistakes.
What It Means for Chemists and Industry
1,3-dibromobenzene illustrates why understanding physical properties matters in everyday science. The melting, boiling, and solubility all affect project steps, from synthesis to purification to storage. Handling guidelines—rooted in E-E-A-T by prioritizing both safety and environmental care—keep people safe and processes efficient. Pulling facts from reputable sources and personal lab trials, the best advice is always: respect the properties, and the chemical rewards careful users with reliable results.
| Names | |
| Preferred IUPAC name | 1,3-dibromobenzene |
| Other names |
m-Dibromobenzene
1,3-Dibromo-benzene |
| Pronunciation | /ˌwʌnˌθriː daɪˌbroʊmoʊˈbɛnziːn/ |
| Identifiers | |
| CAS Number | 108-36-1 |
| Beilstein Reference | 1209246 |
| ChEBI | CHEBI:34682 |
| ChEMBL | CHEMBL12661 |
| ChemSpider | 54606 |
| DrugBank | DB02576 |
| ECHA InfoCard | 03d809c2-08d0-4c95-bcf8-0837b6b18352 |
| EC Number | 205-536-2 |
| Gmelin Reference | 78519 |
| KEGG | C01752 |
| MeSH | D003964 |
| PubChem CID | 69236 |
| RTECS number | CZ9625000 |
| UNII | 90CB87M66M |
| UN number | UN2515 |
| CompTox Dashboard (EPA) | urn:ctfdashboard:7021 |
| Properties | |
| Chemical formula | C6H4Br2 |
| Molar mass | 235.90 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Odor | aromatic odor |
| Density | 1.857 g/cm³ |
| Solubility in water | slightly soluble |
| log P | 3.86 |
| Vapor pressure | 0.17 mmHg (25°C) |
| Acidity (pKa) | <5.73> |
| Basicity (pKb) | Basicity (pKb) : 13.38 |
| Magnetic susceptibility (χ) | -79.0·10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.595 |
| Viscosity | 2.14 mPa·s (at 20 °C) |
| Dipole moment | 2.15 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 109.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | 84.7 kJ·mol⁻¹ |
| Std enthalpy of combustion (ΔcH⦵298) | -4013.6 kJ/mol |
| Hazards | |
| GHS labelling | GHS02, GHS07 |
| Pictograms | GHS07 |
| Signal word | Warning |
| Hazard statements | H302, H315, H319, H411 |
| Precautionary statements | P210, P261, P273, P280, P305+P351+P338, P304+P340, P312, P337+P313 |
| NFPA 704 (fire diamond) | 2-2-0 |
| Flash point | Flash point: 108 °C (closed cup) |
| Autoignition temperature | 540 °C |
| Lethal dose or concentration | LD50 (oral, rat): 2200 mg/kg |
| LD50 (median dose) | LD50 (median dose): 3160 mg/kg (oral, rat) |
| NIOSH | SN2975000 |
| PEL (Permissible) | Not established |
| REL (Recommended) | 0.1 ppm |
| IDLH (Immediate danger) | IDLH: 50 ppm |
| Related compounds | |
| Related compounds |
Benzene
Bromobenzene 1,2-Dibromobenzene 1,4-Dibromobenzene 1,3,5-Tribromobenzene |
