1,4-Dibromobutane: Pathways, Properties, and Purpose

Historical Development

The story of 1,4-dibromobutane stretches back more than a century, finding roots in early alkyl halide research. Brominated hydrocarbons showed great promise in organic synthesis circles during the late 1800s, and chemists looked for alkylating agents that could bridge or link specific molecular structures. With the push of industrial chemistry during the 20th century, demand for simple, flexible, and dependable synthons set the stage for the commercial routine use of 1,4-dibromobutane. Its bifunctional nature made it valuable not only in academic research but as a building block in the pharmaceutical and polymer fields. Over the years, processes for making and purifying 1,4-dibromobutane shifted from small-batch glassware to larger, more controlled setups to minimize byproducts and maximize yield. As regulatory scrutiny grew, so did efforts to understand and reduce environmental risks.

Product Overview

1,4-Dibromobutane serves as a clear, colorless to pale yellow liquid and carries a distinct, sharp odor often associated with brominated organics. Industries choose this compound as a promising precursor for manufacturing engineering plastics, specialty polymers, and select pharmaceuticals. Among its standout features, its ability to introduce C4 spacers into molecules and polymers simplifies the synthesis of complex macrocycles and contributes strongly to crosslinking reactions in synthetic chemistry. Its straightforward reactivity makes it a favorite in academic labs as well, where reliability counts in multi-step synthesis.

Physical & Chemical Properties

Known for its moderate volatility, 1,4-dibromobutane has a boiling point near 195°C and a melting point just below freezing. Its density sits at around 1.95 g/cm³, reflecting the presence of two bromine atoms. The molecular structure, C4H8Br2, establishes it as a dihaloalkane—one capable of highly targeted substitution reactions. It demonstrates decent solubility in ethanol, ether, and chloroform, but resists water dissolution thanks to its nonpolar hydrocarbon backbone. The compound decomposes under strong heating or in the presence of UV light, releasing corrosive hydrogen bromide. Prolonged exposure to moisture or strong bases can trigger hydrolysis, but under standard storage conditions, it holds up well, requiring modest precautions.

Technical Specifications & Labeling

Industrial containers and laboratory vials of 1,4-dibromobutane typically display the chemical’s CAS number (110-52-1), the molecular formula, batch number, levels of purity (over 98% in most research grades), hazard symbols, and handling instructions. Labels must cite the correct Hazard Identification Number, as brominated aliphatics present both environmental and health risks. Standard documentation includes safety information, emergency procedures, and quality assays for classification. The paperwork isn’t just about compliance; reliable specification sheets let researchers match the material’s grade to the demands of their protocols, cutting down on surprises and ensuring safe integration into existing workflows.

Preparation Method

Producers often synthesize 1,4-dibromobutane by direct bromination of 1,4-butanediol or 1,4-dibutanol using phosphorus tribromide, hydrogen bromide, or elemental bromine. The process requires careful control of reaction temperature and atmosphere to avoid overbromination and byproduct formation. Industrial methods favor batch reactors equipped with efficient stirring and cooling, capturing evolved HBr and purifying the crude product by distillation under reduced pressure. Routine monitoring during synthesis checks for color, clarity, and gas evolution, ensuring reaction progress matches expected conversion rates. Finer purification with column chromatography or fractional distillation aims to remove trace impurities, halogenated side products, and leftover starting material.

Chemical Reactions & Modifications

1,4-Dibromobutane stands out in SN2 reactions, allowing nucleophiles to displace bromine atoms for a broad variety of alkylation tasks. The compound makes a handy backbone for making cyclic ethers, polyamides, or quaternary ammonium salts, and it serves as a four-carbon linker—lucrative for both organic and materials chemists. In careful hands, its bifunctional design allows one end to anchor to a substrate while the other links to polyelectrolyte chains, drug molecules, or ligands. Chemists have used catalytic hydrogenation to remove bromine or convert the butyl chain for downstream elaboration, all under precisely defined reaction conditions.

Synonyms & Product Names

The chemical world knows this compound under a range of names, including 1,4-dibrombutane, tetra methylene dibromide, and butylene dibromide. Trade and laboratory catalogs sometimes list it as tetramethylene dibromide to emphasize the four-carbon backbone. Synonyms like 1,4-butylene dibromide or butane, 1,4-dibromo-, also appear in regulatory guides and shipping documents. Each name highlights a facet of the same core molecule, reflecting the conventions of naming in organohalide chemistry and ensuring clear communication for order verification and hazard management.

Safety & Operational Standards

Working with 1,4-dibromobutane ought to highlight safety from the start. Contact with skin can bring a rapid irritation or even burns, while inhalation exposes the lungs to corrosive effects and potential systemic toxicity. Strict ventilation, chemical-resistant gloves, goggles, and long sleeves reduce splashing or fume hazards. Laboratories and production lines enforce spill kits and emergency showers in key spots. Fire service response means CO2 or dry powder—no water jets, since that spreads contaminated runoff. Safe disposal follows national rules for hazardous organic wastes, with trace neutralization or incineration as common routes. Routine training and careful labeling prevent accidents and help younger chemists learn risk management skills on the fly.

Application Area

Producers of specialty polymers reach for 1,4-dibromobutane as a straightforward chain extender. Its ability to form strong, covalent links between molecular units gives it a solid spot in synthetic fibers, engineering plastics, and thermosetting resins. The pharmaceutical sector values it in the construction of complex drugs, sometimes using it as a precursor to new organobromine drugs or as a reactant for tailored modifications. Material scientists take advantage of its bifunctionality in creating macrocycles, crown ethers, ionophores, and linkers for advanced molecular architectures. In more focused chemical synthesis, the compound helps join together amino acids, design catalysts, or prepare ionic liquids. Some agricultural chemicals and flame retardants also trace part of their molecular DNA back to this adaptable brominated chain.

Research & Development

Recent years show academic groups investigating alternatives to harsh bromination steps and aiming for greener, solvent-reduced routes to 1,4-dibromobutane. Mechanistic work delves into the specifics of reaction pathways, nucleophilicity, and steric influences on bromoalkane reactivity, with the goal of developing new, more selective transformations. Material science projects continue to explore this compound as a starting point for longer, functionalized chains that impart novel ductility, resistance, or conductivity. Computational studies shed light on electron distribution and reaction energetics, giving chemists more insight into optimizing reactivity for specialty applications. Pharmaceutical research targets derivatives that show improved performance as intermediates in drug development or selectivity as ligands for biomolecular targeting.

Toxicity Research

Toxicity of 1,4-dibromobutane remains a pressing concern for occupational health agencies. Exposure studies on animals document organ injury, neurotoxicity, and hemolytic damage at high doses, prompting development of strict workplace exposure limits. Inhalation and skin contact in humans can result in irritation, headaches, and systemic symptoms, drawing attention to the need for personal protective equipment and air monitoring. Toxicologists continue to assess the compound’s fate in the environment, scrutinizing breakdown rates, pathways, and accumulation effects. Regulatory thresholds reflect a precautionary approach, based on evidence from both industrial cases and structured animal trials. Ongoing analysis compares the relative health risks of dibrominated alkanes versus chlorinated analogs, aiming for the best balance of utility against long-term safety and environmental stewardship.

Future Prospects

Looking ahead, industry and academic researchers agree that brominated intermediates like 1,4-dibromobutane will play a role in tailoring new materials, even as stricter rules nudge manufacturers toward safer substitutes and cleaner processes. Developments in catalysis, green bromination, and biotransformation present opportunities for both smaller carbon footprints and higher efficiency. By harnessing process improvements and alternative feedstocks, chemical engineers see possible reductions in waste and improved recovery methods. Regulatory trends and consumer demand for less persistent, less hazardous chemicals will encourage a search for new homologs or functional replacements. Yet the unique bond-forming capabilities of 1,4-dibromobutane give it staying power as a stepping stone in advanced synthesis, provided producers and users maintain a strong focus on transparency, risk communication, and continuous improvement of operational safety.



What is 1,4-Dibromobutane used for?

The Building Block in Chemistry

Walk through a college chemistry lab, and chances are someone’s working with 1,4-dibromobutane. This molecule looks simple—four carbon atoms in a chain, bromine atoms on either end—but it does heavy lifting behind the scenes in science and industry. Companies use it as a handy tool for building bigger, more complex molecules. In practical terms, it folds into the starting point for a pile of valuable chemicals. If you think about making a chain or a ring in a chemistry set, this compound acts like a versatile bridge.

Helping Synthesize Polymers and Drugs

1,4-Dibromobutane finds a seat at the table in pharmaceutical manufacturing. Chemists reach for it while putting together medicines, especially those structured around five-membered rings like pyrrolidines and piperidines. These rings show up in antibiotics and even treatments for neurological disorders. The development step needs raw materials that join with other pieces with little fuss, and 1,4-dibromobutane does that job well.

I worked on a project a few years ago that looked for a flexible ingredient to tie together two segments in a prototype painkiller. This compound came up a lot in our meetings. We knew its two bromine atoms would react neatly, closing up into just the shape we needed. The efficiency mattered: cutting a few wasted steps from the route can shrink costs and help safe drugs land on pharmacy shelves faster.

Creating Useful Materials

Beyond pharmaceuticals, 1,4-dibromobutane steps into the world of plastics. It lends itself as a cross-linker—someone might say it acts like a set of arms holding two polymer chains together. Manufacturers lean on these cross-linkers to toughen up resins and epoxy surfaces. A tougher plastic on your car dashboard or in some electrical insulation probably owes something to clever chemistry using this molecule.

These materials need to last, and the tight links formed with dibromobutane help their case. That can mean less plastic cracking on cold mornings or less electrical failure in older wiring. Something simple in a bottle in a lab turns into long-term performance out on the road.

Handling and Health Considerations

No one should forget safety. Halogenated compounds like this one aren’t benign. A whiff of its vapor can sting the nose and throat. Spilling it on skin, especially bare hands, leads to irritation and risk of absorption. Safety data sheets shout for gloves and goggles, and I’ve seen peers get lazy and pay the price with persistent rashes. Factories keep careful watch on storage, fire risks, and disposal practices for a reason.

A few studies highlight broader concerns about environmental buildup. Since it doesn’t snap apart quickly in nature, improper disposal leads to contamination. You hear stories about organic synthesis waste showing up in soil or water, raising alarms about long-term effects. Labs and companies now lean into better recycling and closed-loop systems, which can recapture and reuse the material, cutting down how much winds up where it doesn’t belong.

Responsible Use Moving Forward

As research keeps pushing for new drugs and better plastics, the pressure grows to handle 1,4-dibromobutane wisely. Investing in improved containment and recovery systems pays back over time—not just in health or legal savings, but in community trust. For chemists, solid training and respect for safety protocols make daily handling routine. Society relies on these choices, even if the formula goes unseen.

What is the molecular formula of 1,4-Dibromobutane?

Unpacking the Formula of 1,4-Dibromobutane

Chemistry often gets wrapped up in mysterious codes and formulas, but at its core, it tells simple stories. Take 1,4-dibromobutane. At first glance, the name already points straight to its secrets. "Butane" sets the stage for a backbone of four carbon atoms connected in a line, each crowded with hydrogen—until halogens step in. Two bromine atoms attach to the ends of this chain, transforming plain butane into a molecule with a kick.

Lay the structure bare, and the answer jumps out: C4H8Br2. Four carbons (C4), eight hydrogens (H8), and two bromines (Br2). The name ‘1,4-’ means each bromine snags the end positions—one on the first carbon, one on the fourth.

Why the Details Matter

Some people brush past formula details, but I've found real insight shows up in paying close attention. Knowing exactly where those bromine atoms land makes a difference. Chemical behavior depends on positions—reshuffle a bromine, and you change everything from boiling point to the way a molecule fits into a reaction. If you use 1,4-dibromobutane in a lab, like I did as a student, you realize its sharp, solvent-like smell signals volatility. Handling it needs sturdy lab practice, gloves on, and hoods running. A misplaced formula in the notebook, and the whole preparation goes sideways.

This compound isn't just a classroom curiosity. Industry uses it as a building block—especially in making new ring structures called heterocycles, and in weaving together specialized polymers. Its dual bromine atoms act like handles chemists can grab, snip, and bond to other fragments.

Impacts of Getting the Formula Right

Miss the mark on a molecular formula, and trouble follows. The world learned hard chemistry lessons from past mistakes. Forty or fifty years ago, confusion between similar names led to slipped safety standards and costly errors in research and manufacturing. Chemists now double-check their formulas—the molecular formula of 1,4-dibromobutane is not just trivia, it keeps people safe and saves money.

C4H8Br2 does more than answer a test question. It gives clear rules for storage: halogenated compounds have specific needs, and the right formula guides proper labeling and isolation from incompatible substances. Environmental rules target halogenated hydrocarbons for good reason. If handled roughly, organic bromides risk leaking into water supplies and building up in food webs. Regulatory compliance teams use molecular formulas like guideposts.

Supporting Safe and Sustainable Chemistry

Getting formulas right helps young chemists, yes, but it also supports effective sustainability. Industry now tracks where each gram of halogenated waste lands. Clear records, based on correct chemical identities, support recycling and safer disposal. Researchers publish data tied to these formulas—errors get flagged, corrected, and kept out of global chemical databases. These records tell regulators what to expect at the factory, and give emergency responders the facts they need during spills or fires.

1,4-Dibromobutane may seem unassuming, but its formula—C4H8Br2—holds real-world influence, showing just how much a few atoms on a backbone shape everything from lab safety to environmental protection.

What are the safety precautions for handling 1,4-Dibromobutane?

A Closer Look at 1,4-Dibromobutane

1,4-Dibromobutane stands out as a key building block in many organic chemistry labs. Folks use it for synthesizing pharmaceuticals, polymers, and specialty chemicals. Its structure, with two bromine atoms attached, means it’s less forgiving than your run-of-the-mill alcohol or sugar. People who work with it every week know it’s no stranger to causing skin and respiratory irritation. Accidents or carelessness can have lasting impacts—not only because of short-term discomfort but due to potential long-term health effects.

Understanding the Hazards

If 1,4-Dibromobutane touches the skin, redness and burning can show up quick. Inhaling its vapors often leads to headaches, dizziness, or throat irritation. Its volatility doesn’t match industrial solvents like acetone, but spills and splashes are enough to raise flags. This chemical belongs in spaces where proper ventilation isn’t just a box-checking exercise; clean air moves the vapors out, making the air much safer to breathe.

Personal Protective Gear Isn’t Optional

No experienced chemist steps into a lab with 1,4-Dibromobutane without gloves and goggles. Nitrile gloves provide solid resistance and help keep the skin barrier strong. Lab coats and long pants serve as another wall between you and potential contact. Properly fitted goggles—ones that seal around the eyes—stop stray droplets from causing irritation or damage. Some might call this common sense, but experience shows that skipping a step, even for a minute, often ends in regret.

Storing and Moving the Substance

Bottles should rest in chemical cabinets made for toxic or flammable liquids. Keeping containers tightly sealed stops fumes from leaking out and avoids moisture sneaking in. 1,4-Dibromobutane reacts poorly with strong bases or oxidizers, so separating storage matters. After using the substance, check tops and seals before putting bottles away. Carry bottles in secondary containers if heading to another bench or area. This reduces the chance of an accidental spill reaching the floor or skin.

Clean-Up and Waste Disposal

If a spill happens, don’t reach for a regular mop or paper towels. Use absorbent pads meant for chemical spills, then place all material in a designated disposal bag. Even small amounts left behind on benches can cause problems, especially if forgotten. Dispose of contaminated gloves and wipes in hazardous waste bins, not in regular trash cans. For liquid waste, pour leftovers into labeled bottles kept separate from other solvent waste.

Emergency Planning at the Bench

Eye-wash stations and safety showers aren’t just for show, as anyone who’s felt a splash can tell you. Know their location before the bottle’s opened. In a real emergency, rinse the affected area right away and ask someone to call for help. Never work alone while handling chemicals like 1,4-Dibromobutane; another set of eyes and hands can save the day. Proper training—hands-on, not just lectures—gives people the judgment to know what steps to take if things go south.

Everyday Vigilance Makes a Difference

Safety around chemicals builds on habits and personal responsibility. Up-to-date safety data sheets should stay within arm’s reach, and no one regrets investing in training. Regular checks of gloves, goggles, and ventilation turn into second nature after a few years. People keep one another safe by speaking up about risky shortcuts or worn-out gear. Respect for every bottle and label on the shelf comes from seeing what goes wrong if steps get skipped.

What is the boiling point of 1,4-Dibromobutane?

Getting Specific: 1,4-Dibromobutane’s Boiling Point

1,4-Dibromobutane doesn’t usually turn up at the top of household chemical lists. It’s a straightforward organic molecule, used by chemists in labs and sometimes in industry, but its boiling point—about 195 degrees Celsius—carries real importance. During organic synthesis, hitting that number means you’ve reached the point where the liquid turns into vapor. Not just trivia, that number tells you exactly what climate your lab equipment needs to handle, whether for distillation, storage, or moving chemicals between containers. For many, that boiling point keeps lab operations safe and product quality high.

Why Temperatures Dictate Outcomes

I’ve watched more than a few newcomers underestimate the power locked in boiling points. You can’t just “eyeball” safety with solvents. I’ve seen glassware crack because someone believed room temperature safety guidelines translated to all chemicals. With 1,4-Dibromobutane, that boiling point sits above water by a fair margin: 195°C is hot enough to call for heat-resistant gloves and eye protection. Vapors from organobromine compounds get nasty quickly, and inhaling those can set off headaches, dizziness, or even worse. If your fume hood fails, suddenly you’re not worrying about theory, you’re scrambling to air out the lab. Boiling points let you plan for these moments, keeping accidents at bay.

Linking Boiling Point to Chemical Application

Every time you see a chemical’s boiling point, it hints at how easy it is to purify or transform. Chemists use this line in the sand when they separate mixtures. If your solution boils below the solvent, you lose your hard work in a cloud. Getting too close to 195°C means you’re likely vaporizing your 1,4-dibromobutane—wasting money and risking toxic exposure. Boiling points also influence what sort of gadgets can handle certain chemicals. Basic distillation systems won’t cut it for jobs above 100°C. So, as much as it feels like trivia, boiling point values actually decide what goes in your toolbox and what upgrades your workspace needs.

The Bigger Impact: From Research to Industrial Safety

We're talking about a molecule that sometimes acts as a bridge to build more complex compounds—think polymer or pharmaceutical precursors. Processing hundreds of liters outdoors or in giant reactors brings its own set of problems. Factories can’t afford leaks. Supervisors track exact environmental conditions where 1,4-dibromobutane distills or gets recycled. A one-degree mistake might kick off alarms or stop production lines. Each safety protocol, shutoff valve, or pressure release setting draws its logic from numbers like this.

Smarter Practices for a Safer Workplace

Industry and academia still see avoidable mistakes with hazardous liquids. That risk shrinks when educators stop glossing over fundamentals and talk openly about properties like boiling points. Labels should always show clear numbers; digital logs and sensors can sound the alert if temperatures drift too high. On a personal level, I double-check data sheets before starting anything new—even after years in the field. Skipping steps to “save time” usually brings headaches later. Building habits around small details like boiling points sets everyone up for fewer spills, less exposure, and more predictable outcomes.

How should 1,4-Dibromobutane be stored?

Why Safe Storage Really Matters

Every chemical brings its own risk, but 1,4-dibromobutane demands real attention. Even in experienced hands, things slip—caps loosen, bottles sweat, or fumes creep into the room. This compound’s reputation comes from both its usefulness in synthesis and its health hazards. Skin contact brings irritation. Overexposure is trouble for the lungs and nervous system. Once, in a cramped campus lab, I watched a colleague lose a week to lingering headaches after cleaning up a small spill. Better storage would have made that a non-issue.

The Right Container Makes All the Difference

The right vessel offers much more than a place to put a liquid. A tightly sealed amber glass bottle blocks evaporative loss and slows reaction with light. Something as simple as a loose cap will seed that sharp, pungent smell throughout a storage room. It’s never wise to substitute with plastic: many solvents or brominated organics soften the wrong plastics, leak, or break down. Whenever I see a decent chemical room, I find dated glass bottles with etched labels and clean, legible markings. Many disasters start with someone grabbing an unmarked or mismarked bottle. Always keep that label visible—no excuses, especially once a substance calls for a hazmat sign.

Temperature and Ventilation Cannot Be Ignored

Anytime 1,4-dibromobutane sits above room temperature, vapor pressure climbs and fumes start to build. Keeping it cool and in a well-ventilated chemical cabinet avoids drama. I remember one summer power outage: the AC died, and warm bottles started emitting more vapor. Most folks don’t appreciate how fast this sneaks up—one whiff and you find yourself coughing, eyes watering. A storage area with good airflow plus a backup power plan for cooling is invaluable.

Isolation from Incompatibles

Never house this chemical next to oxidizers, acids, or amines. In one overcrowded storage space, sloppy arrangement led to a mix with a strong base—no explosions, but enough heat and fumes to clear the building. Separating chemicals based on their reactivity isn’t just best practice—it's common sense. Store 1,4-dibromobutane away from flammables, keep clear signage, and you’ll sidestep dangerous surprises.

Access, Training, and Accountability

Only trained personnel belong near these bottles. Good labs don’t hand keys to everyone. A logbook for chemical access isn’t just for show; it builds a trail if anything goes missing or wrong. Safety glasses, proper gloves, and a splash apron aren’t optional. I’ve had to clean up after spills from overconfident students who skimped on protection. That leaves real scars—skin, reputation, and future research budgets.

Disposal—Not the Place to Cut Corners

Once 1,4-dibromobutane expires or you finish a project, proper chemical disposal is critical. Pouring it down the drain, even in small amounts, taints water and brings fines. The best labs set up regular hazardous waste pickups so nothing builds up and old chemicals don’t stay forgotten in a drawer. A safe disposal system keeps the community, and the earth, a little healthier.

Summary: Respect the Risks, Protect the People

1,4-dibromobutane brings value to organic synthesis, but the danger is real. Tough regulations—backed by years of labs getting it wrong—aren’t just red tape. The basics never fail: choose the right bottle, keep things cool, separate by reactivity, and hand out responsibility only to those who earn it. Smart storage keeps people safe, research going, and regrets far away.

1,4-Dibromobutane
1,4-Dibromobutane
1,4-Dibromobutane
Names
Preferred IUPAC name 1,4-dibromobutane
Other names Tetramethylene dibromide
1,4-Butylene dibromide
Butane, 1,4-dibromo-
1,4-Dibrombutan
Pronunciation /ˈwʌn.fɔːr.daɪˈbroʊ.moʊ.bjuː.teɪn/
Identifiers
CAS Number 110-52-1
Beilstein Reference 1209288
ChEBI CHEBI:36472
ChEMBL CHEMBL17036
ChemSpider 6923
DrugBank DB14146
ECHA InfoCard ECHA InfoCard: 100.004.218
EC Number 208-898-5
Gmelin Reference Gm. 6572
KEGG C01782
MeSH D004037
PubChem CID 8038
RTECS number EY8575000
UNII 96XTC36K1B
UN number UN2525
Properties
Chemical formula C4H8Br2
Molar mass 215.95 g/mol
Appearance Colorless liquid
Odor Odorless
Density 1.990 g/mL at 25 °C(lit.)
Solubility in water 9.1 g/L (20 °C)
log P 1.98
Vapor pressure 0.23 mmHg (20°C)
Acidity (pKa) 13.3
Basicity (pKb) 15.03
Magnetic susceptibility (χ) -7.72·10⁻⁶ cm³/mol
Refractive index (nD) 1.499
Viscosity 2.03 cP (25 °C)
Dipole moment 2.62 D
Thermochemistry
Std molar entropy (S⦵298) 216.6 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) -24.8 kJ/mol
Std enthalpy of combustion (ΔcH⦵298) -4232.7 kJ/mol
Hazards
GHS labelling GHS02, GHS07
Pictograms GHS02,GHS07
Signal word Warning
Hazard statements H302, H315, H319, H335
Precautionary statements P210, P280, P305+P351+P338, P301+P312, P501
NFPA 704 (fire diamond) 1-2-0
Flash point 98 °C
Autoignition temperature 535°C
Explosive limits Lower explosive limit: 1.1%, Upper explosive limit: 9.3%
Lethal dose or concentration LD50 oral rat 700 mg/kg
LD50 (median dose) LD50 (median dose): Oral rat LD50 = 1070 mg/kg
NIOSH RX8220000
PEL (Permissible) Not established
REL (Recommended) '5 mg/m3'
Related compounds
Related compounds 1,2-Dibromoethane
1,3-Dibromopropane
1,5-Dibromopentane
1,4-Butanediol