Back in the early part of the 20th century, organic chemists like Moses Gomberg sought to understand what happened at the core of carbon-carbon bonds. Experiments that led up to the accidental discovery of free radicals leaned on compounds like 2,3-dimethyl-2,3-diphenylbutane. This molecule became famous because of its role in pioneering the study of organic free radical chemistry. In the past, researchers used laboratory preparations as teaching tools, and many old textbooks referenced it. Throughout several decades, the compound’s unique symmetrical structure kept it interesting for students and researchers alike. People learned from its reactions and stability, so its significance slowly grew as scientists kept exploring free radical mechanisms. Over time, it evolved from a curious synthetic target to a benchmark substance in mechanistic investigations. Its development didn’t follow the path of mass production, and even today, this molecule appears more often in research than in large-scale industrial contexts.
2,3-Dimethyl-2,3-diphenylbutane—sometimes called tetraphenylethane—is an aromatic hydrocarbon derivative with bulky substituents. The molecule stands out because it packs two methyl and two phenyl groups around a butane backbone. This construction brings steric hindrance and influences its reactions in ways simpler alkanes do not show. I’ve seen chemistry classes use it as a textbook example when discussing symmetry and conformational isomerism. Solid at room temperature and often crystalline, the chemical’s bulky skeleton creates challenges for purification but makes it resistant to some forms of chemical attack. Within laboratories, researchers value its stability and distinctive properties.
This compound forms colorless or faintly pale crystals under ambient conditions. Due to the pair of bulky phenyl rings, it refuses to dissolve easily in water, but exhibits moderate solubility in most organic solvents—benzene, ethanol, even ether. Its melting point hovers in the range of 110–115°C, while the boiling point rises steeply, though thermal decomposition usually happens before it ever reaches a liquid state under standard atmospheric pressure. The stiff, overcrowded environment around the central bonds sets this molecule apart from lighter hydrocarbons. Its density calculates at just above 1.05 g/cm³. The molecule resists oxidation under ordinary conditions and shows little inclination toward acidic or basic hydrolysis, but strong conditions produce fragments and radicals, which earned it a historical role in mechanism studies.
Chemical supply houses list 2,3-dimethyl-2,3-diphenylbutane under CAS number 2612-10-8. Its molecular formula reads C18H22. Laboratories usually supply it with purity above 98%, clear markings on safety labeling, and shipping in sealed glass containers. Its molecular weight hits 238.37 g/mol. Since the compound contains no functional groups besides alkyl and aryl substituents, it doesn’t demand moisture-free handling, but protocols discourage exposure to elevated temperatures and strong oxidizing agents. Labeling commonly carries the names “2,3-dimethyl-2,3-diphenylbutane” and “tetraphenylethane”, ensuring clarity for researchers checking reagent bottles.
Classic organic synthesis protocols for this molecule focus on reductive coupling. Labs tend to start with benzil and methylmagnesium bromide or phenylacetonitrile derivatives, steering reactions under carefully controlled temperatures. In Grignard-type reactions, the process runs through an alcohol intermediate, then leverages acid-catalyzed dehydration to yield the butane backbone. Early laboratory workers heated diphenylacetone with sodium amalgam or other reducing metals. The yields rely on purity and precision, and recrystallization from ethanol or ether remains the easiest way to get clean, sizable crystals at the bench. These methods go back generations and still deliver reliable results, even if more modern alternatives provide cleaner or cheaper outcomes for specialty labs.
Despite its hydrocarbon backbone, 2,3-dimethyl-2,3-diphenylbutane displays resistance to most common chemical attacks. The molecular symmetry blocks many electrophilic and nucleophilic reactions, and steric bulk discourages easy access to reactive sites. Still, strong oxidizers such as potassium permanganate can force oxidation, breaking rings or shortening chains. Exposure to radical initiators in the lab—like benzoyl peroxide—can split the central bond, yielding valuable insights into free radical chemistry. Attempts to functionalize the phenyl rings usually demand aggressive conditions, like Friedel-Crafts acylation or sulfonation. These routes open up possibilities for preparing substituted analogues, although isolation and purification challenge most chemists. Cross-coupling or further alkylation sits outside typical use, mainly due to steric challenges.
Anyone looking for this substance may find it labeled as tetraphenylethane, 2,3-di(methyl)-2,3-di(phenyl)butane, or rarely just as DMPDPB. European sources from older literature sometimes refer to it by trade or research codes, but globally, “2,3-dimethyl-2,3-diphenylbutane” gets the most traction. In reagent catalogs, both English and IUPAC names appear to minimize confusion. Historical papers reference the structure under names like “Gomberg’s hydrocarbon,” nodding to its roots in free radical discovery.
Handling instructions stress common sense and lab safety. Though the compound isn’t notably flammable or volatile, inhaling dust or exposing skin to solid product carries potential for irritation. Staff working with bulk quantities should wear gloves and safety eyewear, and avoid breathing any generated dust. Labs routinely store bottles in cool, dry areas—far from open flames or peroxides. Disposal procedures must follow regulations for hydrocarbons, particularly if intermediate products from reactions with the molecule may pose specialized risks. As with many compounds that once carried little regulation, regular reviews of material safety data sheets remain crucial before starting bench work.
Most chemical plants have no need for this substance on an industrial scale. It stays almost entirely inside academic and research contexts. Organic chemists rely on it to benchmark reactions, especially for teaching about free radical cleavage and stereochemistry. Occasionally it acts as a model in studies on bulky hydrocarbon frameworks, sometimes as a reference material for NMR calibration due to its clean, well-separated signals. Over the past five years, a few materials science projects started exploration of aryl-rich hydrocarbons for molecular electronics, but widespread application remains distant. Medicinal chemistry hasn’t found a direct use, simply due to the compound’s lack of reactive sites and bulk.
This molecule’s story keeps growing as young researchers chase new synthetic methods and theorists unravel the mysteries of bond cleavage. Modern quantum chemists have used 2,3-dimethyl-2,3-diphenylbutane as a standard for modeling the thermodynamics of radical formation and delocalization. Some labs in Europe and Japan experiment with functionalized derivatives, seeking materials for organic semiconductors and optoelectronic hardware. So far, only bespoke designer molecules built on the core skeleton hold promise for next-gen, carbon-rich nano-architectures. Analytical labs sometimes add the compound to their toolbox for testing new spectroscopic equipment due to its signal clarity and stability.
Lab safety committees want thorough data before allowing regular use, so toxicity sits under the microscope. 2,3-Dimethyl-2,3-diphenylbutane rarely presents acute hazards at low exposures. Studies in rodents and in vitro show low to moderate toxicity, mainly as a result of its hydrocarbon nature. Chronic data remains sparse because the compound never saw large-scale industrial application. As with many aromatic hydrocarbons, repeated or high-level exposure brings increased scrutiny for potential carcinogenicity. Current regulations treat it as a slight irritant. Environmental releases run a low risk for acute harm, yet standard protocols demand good chemical hygiene, waste control, and spill containment.
Right now, 2,3-dimethyl-2,3-diphenylbutane isn’t about to change the world of industry or medicine, but its role as a teaching and research tool stays secure. Its stability and classic structure make it a reliable candidate in the organic chemistry classroom. New discoveries in radical chemistry or materials science might one day spotlight functional analogs based on this molecule’s crowded framework. If breakthroughs in organic electronics open new possibilities for large, aryl-rich scaffolds, researchers may see a resurgence of interest. For now, it serves as a quiet supporter of chemical education and basic research—a trusted but underappreciated presence in the lab.
Chemistry doesn’t always attract a crowd, yet the nuts and bolts of how a molecule like 2,3-dimethyl-2,3-diphenylbutane comes together can shed some real light on the power of molecular design. Looking at its name, you might wonder how so many methyl and phenyl groups can fit onto one butane backbone. Simply put, this compound starts with butane, a four-carbon chain familiar to anyone who has ever set up a camp stove. On the second and third carbons, the butane molecule grabs both a methyl group (that’s a CH3 chunk) and a phenyl group (the classic C6H5 ring).
Picture a carbon chain — the spine of the molecule — and imagine bulking it up with arms branching out. It’s like someone wanted to load butane up with flashier accessories. Carbons 2 and 3 are the centers of attention. Instead of the usual hydrogen atoms, each of those central carbons gets a methyl and a phenyl group. You end up with a molecule that looks a little like a two-armed dancer, phenyl rings in each hand and methyl groups as shoulder pads, with the butane chain as the body.
A structure like this isn’t some academic curiosity — these bulked-up hydrocarbons can teach us a lot. In the lab, a rigid, crowded molecule behaves differently. The presence of the four large groups on two side-by-side carbons creates a pretty significant physical bulk. It has an effect on melting point and solubility, both of which chemists check regularly to gauge purity and behavior in real-world reactions. From my own experience as a student, just one extra branch on a carbon chain could turn a sticky oil into needle-like crystals straight out of solution.
For those who think all hydrocarbons are created equal, this molecule proves otherwise. The tangle of phenyl rings and methyl groups blocks reactions at those central carbons. That’s not just a textbook fact — anyone trying to react this molecule might find out quickly that bulky groups can really slow things down, making this compound much less reactive than plain butane or even a simple alkylbenzene.
2,3-dimethyl-2,3-diphenylbutane brings chirality into the mix. Each central carbon can act like a left or right hand — that gives you more than one possible version of the compound. These variants, called stereoisomers, interact differently with other chiral molecules, which is a big deal for pharmaceuticals and fine chemicals. In the real world, the differences between these isomers can decide if a drug works or causes trouble.
A molecule packed with groups like this hasn’t just been drawn for fun. Chemists use it to test ideas about steric hindrance, reaction rates, and the way electrons move through crowded spaces. I remember seeing models of this compound in chemistry class — the sheer bulk kept the central carbon atoms from doing much work, which drove home the point that atoms aren’t just dots on a page.
The lessons from a molecule like 2,3-dimethyl-2,3-diphenylbutane go far beyond the lab. Understanding what makes a molecule too bulky to react helps researchers design safer drugs, better plastics, and more selective catalysts. Instead of guessing, they can use molecules like this one as reliable roadblocks or building blocks, steering chemical reactions where they need them to go. This structured approach keeps chemistry practical — and, for those of us who like hands-on problem-solving, that’s a welcome thing.
2,3-Dimethyl-2,3-diphenylbutane won’t ring a bell for most folks. In research circles though, its structure draws attention. With bulky, symmetrical groups and a backbone to support them, this compound becomes a go-to for certain chemistry puzzles. Walking into a university lab, shelves packed with colored glassware, you can spot bottles of this compound next to catalysts, solvents, and delicately labeled samples. There’s an energy among chemists, often chasing ways to use molecules like this to open new doors in experimenting and manufacturing.
Catalyst work sometimes gets swept under the rug, but here’s where 2,3-dimethyl-2,3-diphenylbutane can claim a spot. Its shape helps it act as a hydrogen donor in transfer hydrogenation – a process many industries rely on to turn harsh reactions into gentler ones. In simple words, that means scientists use it to add hydrogen to molecules without running the risk and expense of high-pressure hydrogen gas systems. Back when I interned with a pharmaceuticals company, researchers pointed to this compound as a safer stand-in for trickier hydrogen sources. They needed to tweak the structure of drug candidates by adding or removing hydrogens. This simple switch turned a tedious task into a predictable, safer step.
Anyone who’s tinkered with organic synthesis knows the gaps that bulky molecules can fill. 2,3-Dimethyl-2,3-diphenylbutane doesn’t naturally show up in grocery-store chemicals. Its size and shape let it act as a temporary “blocker” during multi-stage syntheses. Chemists use it as a protecting group or a steric shield, stepping in to prevent reactions from going where they shouldn’t. Think of it as the tape you slap over half-painted molding: block off the parts you don’t want touched, make your changes, then peel it off. In laboratories, it’s standard to pull out a stash of this compound for just such purposes, especially in research that deals with sticky, stubborn molecules refusing to cooperate in complex reactions.
Some compounds are like red herrings—they look useful, but folks really want to see how they behave. Scientists use 2,3-dimethyl-2,3-diphenylbutane as a “probe” to run experiments about radical reactions. Its symmetrical design means that results aren’t masked by hidden factors. Graduate students, tasked with figuring out radical pathways, grab this molecule to simplify the mess. In my own coursework, teachers loved using it to show textbook reactions, where products become easy to analyze and teach.
Every specialty compound comes with hurdles. The cost and sourcing of 2,3-dimethyl-2,3-diphenylbutane can be restrictive for small labs. Producing it takes care—a bad batch can ruin months of work. Some companies have stepped up, finding new ways to make this compound more efficiently. A friend of mine in the chemical supply business started offering smaller lots and purer samples, giving research groups a break on costs. There’s also a push to design compounds that deliver similar results but feature green chemistry practices. As technology rolls forward, industries and universities keep hunting for better, cleaner, and safer upgrades for reactions where this molecule currently shines.
2,3-Dimethyl-2,3-diphenylbutane doesn’t make headlines like sodium does, but it quietly holds its own in the family of organic compounds. With a name like that, the structure surprises nobody: four benzene rings for bulk, plus a stubby butane skeleton. You won’t find this molecule dissolving in your mug of tea. It’s a hydrocarbon through and through, which means it shrugs off water. Run it through most common solvents—think ether or hexane—and you’ll see it blend right in.
In my college labs, anything with several rings like this tended to look like pale crystals rather than liquid. That rings true here: 2,3-dimethyl-2,3-diphenylbutane forms white or off-white crystals, hard and sometimes clumpy. The melting point tops 110 degrees Celsius, much higher than anything found in your kitchen. Holding a sample in your hand, you realize it won’t melt unless you really turn up the heat.
Benzene rings, stacked onto that backbone, give this molecule a stubborn stability. It takes a lot to get 2,3-dimethyl-2,3-diphenylbutane to react. Toss it with strong acids or bases, and most of the time it doesn’t blink. It’s not the type to grab oxygen or chlorine and change overnight. This makes sense, knowing how hydrocarbons with so many rings behave: almost nothing besides strong oxidizers moves the needle.
The molecule’s bulk means it isn’t about to slip through cell membranes or mix with blood. In industry, that limits what it can do. You don’t see it showing up in health supplements or agricultural sprays. Instead, it gets used by chemists looking for a strong, non-reactive backbone—often as a supporting character rather than the lead.
What pops up as a problem? Solubility. 2,3-dimethyl-2,3-diphenylbutane barely mixes with anything polar, so washing it out with water won’t work. Dispose of it wrong, and you risk polluting rivers, where it just floats along, stubborn and unchanged. Labs with a green streak keep a close eye on how much they use, and they lean toward solvents that can break it down completely.
Then there’s purity. If a job calls for serious precision—like pharmaceuticals—any leftover trace of this compound could cause trouble. It’s hard to separate from similar molecules using basic techniques. Chromatography often steps in. The method strips away contaminants, but it costs time and cash.
Safer disposal stands as the most pressing concern. Catalytic incineration, using strong oxidizers at high heat, offers one way out. That breaks it down to carbon dioxide and water, no fussing with residue. Education helps too: anyone handling this molecule should know proper protocols, not just toss byproducts down the sink. Looking further, designing compounds with similar physical heft but better environmental breakdown traits could give future chemists options with less baggage.
2,3-Dimethyl-2,3-diphenylbutane sits closer to the sidelines than to the spotlight, but plenty of lessons come from how it’s built—and how we deal with it long after lab time ends.
2,3-dimethyl-2,3-diphenylbutane doesn’t cross most people’s minds outside a chemistry lab, but it pops up in interesting places for those drawn to organic synthesis. Not every day does one look up how to make this molecule, yet it’s got an odd charm. You see, the path to this compound gives a peek into how chemists can shuffle, bond, break, and rebuild things in ways that would be unthinkable with bigger objects. To make something as intricate as this, the tools don’t come out of the kitchen drawer; they call for real planning and a touch of daring.
Everything begins with benzil and a reducing agent—often aluminum amalgam or zinc in the company of acid does the job best. Benzil’s structure delivers the right shape and reactivity. Trying to use something else quickly becomes trouble: you’re left dealing with side products, wasted time, or a dead end with no sign of a reaction.
Getting from benzil to 2,3-dimethyl-2,3-diphenylbutane is all about pinacol coupling. Take benzil, swirl it up with your chosen reducer, and watch as the carbonyl groups collapse into alcohols, then snap together to form a new carbon–carbon bond. This bond is what links two bulky phenyl rings, each flanked by a methyl group, right in the center of the molecule.
DIYers in the field have stories about this step going sideways if someone tweaks the amounts or skips careful monitoring. For a smooth ride, you want the right temperature and patience. Rush things, and you risk making unwanted byproducts, and you’ll spend half your day at the bench trying to fish out the real product.
Every synthesis leaves behind leftovers. Once that chunky mixture settles, crystals of the target compound start to appear. Extraction with solvents and a round through recrystallization filters out the rest. The smell, the look, the slow forming of crystals—it satisfies in a way textbooks can’t describe. Attempts to shortcut this part can mean going back to square one. True, sometimes chromatography gets involved if impurities cling on stubbornly, but for most, plain recrystallization does the trick.
Some folks wonder who chooses to make such compounds. For the curious, this synthesis isn’t just about the product but about mastering control. There’s a sense of building something new—one molecule at a time. Beyond the challenge, the process shines a spotlight on radical mechanisms. Student chemists get hands-on with reductive coupling, seeing theory spring to life, and folks in research use molecules like these to probe how reactions work or to shape new drugs.
How could things get better? Better yields never hurt. Modern chemists scan for new catalysts, tweak solvents, chase greener methods, all aiming for cleaner reactions and less waste. Research into electrochemical reductions stirs excitement too—no heavy metals, less environmental mess, and a nod toward sustainability. Labs willing to try different temperatures, stick with safer reagents, and adapt equipment often end up with safer, better processes. Every improvement saves real resources and lets more people join in, not just those with deep budgets for fancy chemicals.
Nobody gets far in organic synthesis without some failures. Bottled chemicals offer promise, but results rest on careful preparation, endless curiosity, and the stubbornness to repeat runs until the crystals at last glimmer in the flask. For me and others who toil at the bench, every attempt strengthens appreciation for the complexity and beauty hidden in each reaction.
Few people have heard of 2-3-dimethyl-2-3-diphenylbutane outside a chemistry classroom, but anyone around organic labs should care. The old joke about “double-gloving and crossing your fingers” lands flat once you see a spill up close. Aromatic hydrocarbons like this one don’t care that your semester project depends on them—skin contact can bring irritation, headaches hit hard from the fumes, sometimes dizziness sets in before you know it. Respirators often feel over the top for benchwork, yet breathing in any amount of volatile organics has a way of catching up to people who play fast and loose.
The more we see about long-term health, the clearer it gets: wearing splash goggles and gloves is non-negotiable. Lab coats protect against more than one ruined shirt. I once watched a postdoc scramble because he didn’t read the fine print. The bottle slipped, cracked, and suddenly the room stank of chemicals. We aired out the space, but after that the safety data sheet stopped collecting dust. Chemicals like this often light up under the right spark—so open flames or static near your workspace make for anxious colleagues.
If you’ve handled acetone or toluene, you know the drill: tight lids, fume hoods, keeping everything clean before and after use. The hoods matter more than people admit—fume hits different compared to water vapor, and the payback is quick. Don’t trust just about any container, either. Hydrocarbons want glass or approved plastic, nothing that can melt or react. Solid benches, paper towels for quick grabs, and secondary containment go a long way; labs get messy, but it’s on us to cut down on the chaos.
There’s nothing macho about skipping proper labeling. Vials left without dates mean someone’s in for a surprise later, maybe something explosive, maybe just a panic. Too many times, it comes down to the person in a rush—rushing is maybe the root cause behind half the stories folks swap after hours.
The best solution is shelving away from sunlight and heat. Chemicals like these prefer dark, steady environments—think a cool, dry chemical cabinet, not a cluttered back bench where spills get ignored. Never stack them near oxidizers or acids. If you’re lucky, nothing reacts; if you’re not, you clean up more than a small mess. I saw an exhaust hood fill with smoke because bottles touched when they shouldn’t. Since then, segregating based on compatibility isn’t just a theory but a policy across most real labs.
If you work after hours, double-check access restrictions. Keys and logbooks seem dull until something goes missing. When people know who had what and when, responses come quicker.
Training needs to mean more than clicking through boring PowerPoints. Nothing beats talking through what can actually happen—sharing stories, even embarrassing ones, gets people to take care seriously. The more we rely on outdated habits, the more we risk short cuts. Labs could offer easy-to-grab PPE at every entrance, keep signage sharp, and stop treating accident drills like a chore. A positive safety culture pays off—a giggle about “glove fashion” is better than someone heading to the ER.
We work alongside chemicals we sometimes barely pronounce, yet small steps cut big risks: stay alert, label everything, store with intent, speak up when something’s off. If it’s part of our daily routine, we all walk out just fine.
| Names | |
| Preferred IUPAC name | 2,3-dimethyl-2,3-diphenylbutane |
| Other names |
2,3-Dimethyl-2,3-diphenylbutane Tetramethylstilbene 2,3-Diphenyl-2,3-dimethylbutane |
| Pronunciation | /tuː θri daɪˈmɛθɪl tuː θri daɪˈfɛnɪl ˈbjuːteɪn/ |
| Identifiers | |
| CAS Number | 1889-67-4 |
| 3D model (JSmol) | `JSmol.loadInline("data/mol/2,3-dimethyl-2,3-diphenylbutane.mol");` |
| Beilstein Reference | 1841511 |
| ChEBI | CHEBI:51968 |
| ChEMBL | CHEMBL454234 |
| ChemSpider | 2036443 |
| DrugBank | DB16624 |
| ECHA InfoCard | 100.013.062 |
| EC Number | 211-234-4 |
| Gmelin Reference | 57268 |
| KEGG | C08365 |
| MeSH | D016723 |
| PubChem CID | 69908 |
| RTECS number | EL8750000 |
| UNII | T8Y91Q1B4N |
| UN number | UN3077 |
| Properties | |
| Chemical formula | C18H22 |
| Molar mass | 362.50 g/mol |
| Appearance | White solid |
| Odor | Odorless |
| Density | 1.008 g/cm³ |
| Solubility in water | Insoluble |
| log P | 4.88 |
| Vapor pressure | 0.0000227 mmHg at 25°C |
| Acidity (pKa) | ~50 |
| Magnetic susceptibility (χ) | -72.54 × 10⁻⁶ cm³/mol |
| Refractive index (nD) | 1.5610 |
| Viscosity | 1.4 cP (20°C) |
| Dipole moment | 0.0 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 273.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | 224.3 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | -7114 kJ·mol⁻¹ |
| Hazards | |
| GHS labelling | GHS02, GHS07 |
| Pictograms | GHS07 |
| Signal word | Warning |
| Hazard statements | H319: Causes serious eye irritation. |
| Precautionary statements | P261, P273, P301+P312, P305+P351+P338, P337+P313 |
| Flash point | 145 °C |
| Autoignition temperature | 425 °C (797 °F; 698 K) |
| Lethal dose or concentration | LD50 oral rat 4300 mg/kg |
| LD50 (median dose) | LD50 (median dose): 1300 mg/kg (oral, rat) |
| NIOSH | SN8750000 |
| PEL (Permissible) | Not established |
| REL (Recommended) | Not established |
| Related compounds | |
| Related compounds |
2,3-dimethylbutane 2,3-diphenylbutane benzene toluene ethylbenzene stilbene |
