People first studied catechol over a century ago, but the real focus on Bis(Catechol) came with the boom in coordination chemistry. Chemists noticed that pairing two catechol units through metal or organic linkages brought new properties — changes in redox behavior, improvements in solubility, and different ways of sticking to metal ions. Research picked up as analytical tools like NMR, IR, and mass spectrometry got better. By the 1970s and 1980s, laboratories started cataloging its ability to serve as a building block for chelates and sensors, and interest spread across Europe, North America, and Japan. The original curiosity about simple aromatic compounds became a hunt for molecules with more bite or more selectivity. This journey reflects how basic synthetic ideas keep shaping applied materials: start with a simple phenol, combine two with just the right bridge, and suddenly you get a versatile molecule for the modern lab.
At its core, Bis(Catechol) pairs two catechol rings, usually joined by an alkyl, aryl, or metal bridge. Chemical suppliers typically deliver it as a powder or crystalline solid, showing a tan or pale brown color. You often find it under the labels "bis(2,3-dihydroxyphenyl)" or "di(catechol) compound," with product numbers varying from batch to batch. Specific forms include Bis(catecholato)metal complexes, which pop up in analytical kits, battery research, and catalysis. Manufacturers push for high purity, often greater than 98%, with careful filtration to keep heavy metals and organic contaminants low. Research labs favor products with clear documentation, batch consistency, and standardized container sizes, ranging from small vials for bench-scale trials to jars supporting kilogram-scale syntheses.
Bis(Catechol) stands out because it mixes aromatic rigidity with flexible side groups. Melting points start around 180°C, though metal-bridged forms can hold solid up to 300°C. Solubility skews toward polar solvents—think DMSO, ethanol, and acetonitrile—with modest water compatibility due to hydrogen bonding rather than simple dissolution. UV-Vis absorbance shows distinct peaks in the 270–290 nm range, a fingerprint for tracking behavior in synthesis and application. Redox potential often runs close to that of single catechol, but the linkage shifts electron flow, fine-tuning reactivity. Storage depends on keeping out moisture and strong light; the powder stains skin easily and can leave gray marks on glassware due to mild chelating action.
Suppliers print relevant data directly on bottles and spec sheets. Labels typically list the full chemical name, structural formula, batch or lot number, and storage instructions—“keep at 2–8°C, dry area, dark bottle.” A purity assay (sometimes by HPLC, sometimes GC if volatile impurities are a problem) shows real-world working quality. Heavy metal testing, usually by ICP-MS, reassures users targeting sensor or pharmaceutical work. You’ll spot warning graphics for skin or respiratory irritation and clear guidance on personal protection, aligning with GHS standards. Detailed safety datasheets travel with every shipment, and QR codes link to digital technical libraries so chemists can double-check on-the-fly questions about compatibility and performance.
Making Bis(Catechol) starts with commercial catechol, which comes from petroleum feedstock or wood tar. The linker’s chosen based on target use: for basic research, many rely on condensation with formaldehyde under mild acid or base, which gives simple methylene-bridged forms. Other syntheses connect two catechols with organosilane, carbonate, or even phosphorus-based bridges, where control of reaction time and temperature tunes product yield and structure. Metal-linked variants demand a more elaborate playbook: dissolve catechol and a metal salt (say, iron or titanium) in water or ethanol with careful stirring to avoid clumping, then precipitate the product by neutralizing with a gentle base—avoiding oxygen as much as possible to prevent uncoupled side products. Purification sticks to filtration and recrystallization, using acetone or ethyl acetate to strip away side reactions and give a clean powder for analysis.
The business end of Bis(Catechol) lies in its two sets of ortho-dihydroxy groups. Chemists take advantage of these for everything from cross-couplings to Michael additions. Reactivity opens the door to further modifications: sulfonation and nitration change water solubility, carboxylation tweaks chelating action, and heavy metal ions coordinate between the rings for use in redox-active materials. Polymer chains built from Bis(Catechol) form strong adhesives, evoking the natural chemistry of mussel byssus. Functionalizing the aromatic rings lets scientists attach fluorescent tags or anchor groups for binding nanoparticles. In spent catalysts, recovery runs through acid washes, converting Bis(Catechol) complexes back to free ligand for recycling—a nod to both cost and green chemistry pressures in industrial labs.
Names crop up in catalogues and patents: some listings call it "bi-catechol linker," others "catechol dimer," "catecholato ligand," or "1,1'-bis(2,3-dihydroxyphenyl)." For metal complexes, inserts like “ferric bis(catecholate)” or “titanium bis(catecholato)” pin down the precise application. In biological circles, references pop up to “dicatecholamines” and similar handles. Each supplier favors trademarked names alongside IUPAC descriptors, which can trip up newcomers checking safety sheets or regulatory guidelines. So, most advanced users fall back on the structural formula or CAS number to avoid confusion across countries and brands.
Laboratories set strict ground rules for working with Bis(Catechol). Skin and respiratory sensitization stand out as the big concerns. Gloves, goggles, and fume hoods come as standard kit, regardless of the batch size. Spills call for immediate cleanup—solid or solution—since staining and contamination risk both lab benches and wastewater. Eye-wash stations get used once in a while when splashes turn up, thanks to the mild but persistent irritant effect. Industrial settings often add air extraction systems and spill kits with activated carbon or specialty pads, guided by local regulations and internal audits. Waste goes out in labeled chemical bins rather than general trash, reflecting the chelating activity and water system pressure from even low-level release. Regular monitoring and bench manuals reinforce the message: treat every spill or splash as a fixable lesson, not just a hazard.
Uses explode outward from simple synthesis. Electrochemistry labs pick up Bis(Catechol) for electrode coatings, where the ligand improves selectivity for metal ion detection. Polymers made from Bis(Catechol) serve in biomedical glues and tissue scaffolds, copying the behavior of adhesive marine organisms. Chemical sensors benefit from its redox activity, providing a signal boost in detecting trace transition metals or environmental pollutants. In energy storage, metal-Bis(Catechol) complexes make their way into next-generation battery cathodes, offering more cycles and less drift. Analytical chemists lean on specialized derivatives for high-performance liquid chromatography or as markers in mass spec workflows. Even art conservation groups test Bis(Catechol) polymers as reversible coatings for delicate paper and canvas. The molecule’s reach shows how chemists keep finding solid uses for old workhorses.
Recent years bring a run of fresh ideas. Biotechnology teams engineer catechol features onto peptides and proteins, boosting interface strength in biosensors and implant coatings. Green chemistry labs chase renewable linkers—making Bis(Catechol) from lignin or plant-based feedstocks—to cut the fossil footprint and unlock new properties. In catalysis, researchers test new metal bridges to crank up electronic effects or change selectivity in industrial oxidation processes. Drug delivery studies try out Bis(Catechol)-drug conjugates for targeted release, while surface chemists build up nanocoatings for corrosion resistance and electronics. Funding agencies love cross-disciplinary work, so labs link Bis(Catechol) to nonmetal partners or put it into bioinspired architectures for soft robotics. Each effort folds in lessons learned from physical chemistry, safety, and downstream recovery—keeping R&D grounded in both challenge and return.
Animal and cell culture studies flag moderate risks tied to Bis(Catechol). High doses spark liver and kidney changes, especially in rodents and aquatic species, due to the molecule’s tendency to generate reactive oxygen species or bind trace metals in biochemical pathways. Human in vitro tests confirm skin and eye irritation, with dose- and time-dependent effects. Long-term exposure rarely turns up in the general environment but matters for occupational health—especially where synthesis, formulation, and disposal aren’t tightly controlled. Some research points to breakdown products with greater biological activity, so ongoing monitoring tracks not only acute toxicity but also metabolic by-products in wastewater and soil. Regulators in Europe and North America ask for detailed risk assessments before new derivatives see broad application, especially in food-contact materials or biomedical fields. Training and workplace controls remain the best day-to-day defenses against avoidable harm.
Experience suggests applications of Bis(Catechol) will widen as more industries push for sustainable chemistry and advanced materials. Scientists keep finessing its structure to control everything from biodegradable electronics to targeted metal capture in mining wastewater. Progress in renewable feedstocks and mild manufacturing methods hints at scalable, low-impact production lines. Regulatory trends shape how and where new derivatives move out of the lab—biomedical, environmental, and electronic sectors all seek greener, safer, or higher-performing tools. Upcoming advances may unlock invisible-to-the-eye coatings on textiles or embedded sensors in food packaging, changing how we interact with basic consumer goods. The molecule holds ongoing challenges around toxicity, recovery, and smart design, but its adaptability and strong chemical backbone point to a steady stream of breakthroughs.
Bis(catechol) comes up in conversations about both chemistry and materials science. With a name like that, it sounds right out of a lab, and that’s no accident. The core structure — two catechol groups linked to a central atom — makes this molecule much more than an academic curiosity. I remember the first time I handled it in a research internship; the lab supervisor described it as “sticky in more ways than one.” He meant that quite literally, since one of its primary roles shows up in the development of adhesives, inspired by the way mussels grip to rocks.
Some scientists look at mussels and see a solution to a sticky problem. These creatures cling to wet surfaces, even underwater. That’s where bis(catechol) steps in. Its structure mimics the way mussels use catechol to bind to just about anything — glass, metals, even plastic. This means adhesives built with bis(catechol) actually hold up under water or on surfaces that regular glue can’t handle. Years ago, surgeons started hunting for better options to seal wounds quickly. Synthetic glues based on bis(catechol) chemistry could do that job in wet, messy environments like inside the body.
It’s easy to overlook the quiet workhorses of the chemical industry, but bis(catechol) compounds play a part in making oxidation-resistant coatings. Air and moisture wear things down, but a coating that includes bis(catechol) resists both, keeping metal parts from rusting or tarnishing. Factory equipment gets another lease on life with this technology. My father once worked in maintenance, and he saw the difference between parts treated with older coatings and the new catechol-infused versions. The ones with catechol barely showed a spot of rust.
Researchers don’t just stop at glue or coatings. Bis(catechol) chemistry stretches into controlled drug delivery. Some molecules need a ride to certain tissues, and scientists tether medication to bis(catechol) units that can then cling firmly to surgical implants or bone. This means those drugs release slowly and where they’re most needed, instead of flooding the whole body. Dental adhesives and bone cements get tougher and more reliable with these tweaks, leading to better patient outcomes.
Anyone working in waste management or recycling sees value in compounds that can “grab” metals. Bis(catechol) forms what chemists call chelates with heavy metals, which is a fancy way to say it locks them down and won’t let go. That property matters in water treatment. Pulling out lead or copper from industrial wastewater takes finesse. Add bis(catechol), and suddenly those metals have nowhere to run. It’s a game-changer for communities trying to keep their water clean without breaking the bank.
The versatility of bis(catechol) keeps pulling new researchers in. But any new chemical, no matter how promising, gets attention for its safety profile. Academic studies from major labs stress testing for toxicity and biodegradability. No one wants a miracle adhesive that ends up causing harm to living systems or builds up in rivers.
Every time I watch a science documentary, I think about how these small molecules sneak into so many different parts of modern life. Bis(catechol) might sound niche for now, but the push for stronger, greener, and more adaptable products means its story is still unfolding.
Bis(catechol) rests on a simple but powerful framework. It’s built from two catechol units that link up through a central atom or functional group, depending on the type. The basic catechol structure gives bis(catechol) its remarkable chemical traits. Catechol itself comes with two hydroxyl groups attached to a benzene ring, which brings both polarity and reactivity. Putting two catechols together amplifies those features—raising the stakes for how this molecule behaves and where it can show up in a lab or industry.
Bis(catechol) exhibits good solubility in polar solvents like water or alcohols. In research, I watched technicians mix it into solutions for metal ion testing without trouble—no cloudiness, just clear readiness. That ease of mixing comes from those hydroxyl groups, which latch onto water molecules through hydrogen bonding. But the real punch comes from its ability to bind metal ions. Each catechol arm donates electron pairs, creating strong metal-ligand interactions. Scientists take this property seriously; it turns bis(catechol) into a useful chelator. For example, chemists use it to collect heavy metals or to stabilize metals in industrial processes.
Catechols flip between reduced and oxidized forms with little prompting. Expose bis(catechol) to air or basic conditions, and it starts changing color—a visible sign that oxidation is underway. This tendency for redox cycling brings both challenges and creative opportunities. On the one hand, it can limit storage life or cause unexpected reactions if the surrounding environment isn’t carefully managed. On the other, those redox shifts drive unique catalytic reactions and feed into advanced battery research. Bis(catechol)’s reversibility mirrors the life-and-death cycles seen in natural molecules, like the catechols in living tissues. This trait attracts scientists aiming for greener, more adaptable technology.
Safety data show that handling bis(catechol), like handling any phenolic compound, requires good laboratory habits. The reactive hydroxyl groups make it irritating to skin and eyes on contact. Meanwhile, its tendency to bind metals means spills could draw up environmental toxins. Researchers and workers always use gloves, goggles, and fume hoods for a reason—they’ve seen firsthand how easily such chemicals pass through regular safety nets. In my experience, clear lab protocols and emergency steps prevent nearly all accidents. Still, questions about long-term environmental persistence hover over many catechol-based chemicals, reminding us not to take disposal lightly.
Chemists and engineers keep pushing bis(catechol) into new territory. Its ability to tie up metals inspires water purification schemes, both for cleaning industrial runoff and for capturing rare elements. In the field of materials, bis(catechol) chemistry led to strong adhesives modeled after the sticky proteins that mussels use to cling to rocks. Research groups have harnessed its redox action for electrode coatings and next-generation sensors. These practical applications grow from a deep understanding of its chemical roots: solubility, redox ability, and robust metal coordination. Responsible use starts with thorough knowledge and a mindset trained to look for both risks and rewards.
Bis(Catechol) shows up in academic labs and some niche industries, linked to materials science research and specialty chemical work. It does not carry the notoriety or wide familiarity of solvents or acids that fill every shelf, but it comes with its own handling quirks. Over the years, students and professionals alike have had batches go bad because small storage mistakes snowball into product loss or real risk.
Chemists often learn the hard way that moisture and oxygen play the villain roles with Bis(Catechol). Catechol rings, with their exposed hydroxyl groups, draw in water from the air. Left open even for a short time, Bis(Catechol) clumps up or takes on a brownish color, and purity drops. Such changes quietly sabotage experiments, especially in sensitive coordination or polymerization reactions that demand clean, dry reagents for trustable results.
Direct light speeds up degradation, so a tinted glass bottle does more than look fancy. If you have access, choose amber bottles—a simple detail that blocks UV and cuts down on light-driven breakdowns. Many labs toss reagents in clear flasks because it’s easier to see levels, but with Bis(Catechol), going for darker glass keeps the chemical in good shape for longer stretches.
Temperature may not top the list of worries for some organic materials, yet with Bis(Catechol), cool storage makes a big difference. A lab-grade fridge set around 2–8°C gives the optimal range. Room temperature, especially in humid or hot climates, invites both water uptake and faster aging. Freezer storage often isn’t needed; just aim for conditions that discourage volatility and airborne contaminants.
Air brings in not just oxygen but invisible moisture. Every time you uncap the bottle, a fresh dose of both drifts onto the surface of Bis(Catechol). Sealing the original container with a screw-cap lined with a Teflon or polyethylene gasket works well. For labs that cycle through Bis(Catechol) regularly, swapping the bottle’s air with inert gas—such as nitrogen or argon—gives added security. Gloveboxes or Schlenk lines offer added protection, but for smaller amounts, even a shot of dry argon before recapping makes a difference.
Desiccators remain one of the overlooked but reliable options. Storing the bottle with a few pellets of drying agent, like silica gel or anhydrous calcium chloride, soaks up stray moisture. For glass vials, adding a fresh packet every few weeks extends shelf life. I’ve seen chemicals last for years using this method, compared to the sticky lumps and yellowing that come from shelf-top neglect.
Vague or lazy labeling leads to confusion and frustration, especially if you share lab space. Always write the transfer date and initials on every container. That way, nobody grabs partly degraded Bis(Catechol) thinking it’s pristine. Gloves and goggles should always stay close at hand—direct contact with catechols irritates skin and eyes. Small accidents from shortcuts often cost more than a few seconds spent preparing right.
Disposing of stale Bis(Catechol) means using approved chemical waste bins, not washing it down the drain. Even small amounts, if handled carelessly, can throw off sewage systems and create environmental risks. Coordinating with local hazardous waste disposal services keeps dangers out of waterways, and most institutions run annual collections for expired specialty reagents like Bis(Catechol).
Following these habits has saved time, money, and project outcomes in the labs where I’ve worked. Tools like cold, dry, and dark storage, solid labeling, and thoughtful container choices all help stave off the headaches that come from degraded materials. A little planning goes a long way to avoid wasted experiments and chemical risk.
Bis(Catechol), a chemical usually encountered by materials scientists and researchers, steps into the spotlight due to its growing applications in adhesives and as a starting material for a handful of organic syntheses. The way this substance interacts with its environment draws attention, since a regular day in the lab can quickly turn sour if safety around chemicals is ignored.
I’ve spent hours hunched over lab benches, running extractions, mixing reagents, and nervously checking chemical compatibility charts. Eventually, anybody taking care of their health in a lab digs into the safety data sheets. Looking up Bis(Catechol), I find reminders from regulatory bodies: this compound carries real hazards.
Contact with the skin promises more than a minor irritation. According to several chemical safety boards, Bis(Catechol) triggers a severe response if it soaks in through skin or splashes into eyes. Extended inhalation of the dust or vapors ends up affecting the respiratory tract. Suddenly, lack of caution starts looking more costly than saving a few minutes.
The National Center for Biotechnology Information (NCBI) and PubChem catalogs report that catechols and their derivatives interfere with metabolic pathways and can cause oxidative stress. In the short term, symptoms often fold into basic lab mishaps—burning sensation, sneezing, coughing—but no one wants to find out how repeated, long-term exposure plays out.
One supervisor repeated this lesson: gloves and goggles protect more than just your skin; they buy escape time during spills. Once, in a research group meeting, I learned about a grad student who brushed off a tiny Bis(Catechol) spill and spent the afternoon with a rash creeping up her arm. It cost her a morning at the university health clinic and a few days off her experiment schedule.
Standard cycle: cutting corners with safety, then paying double in recovery time and administrative hassles. It echoes through chemical labs everywhere. Strong air filtration, gloves made from nitrile instead of regular latex, and face shields become less a matter of bureaucracy and more about respecting how unforgiving certain chemicals can be.
It makes sense to treat Bis(Catechol) with the same seriousness as you would cyanides or strong acids. Safe work starts before opening a bottle—solid awareness, written protocols, training new hands on cleanup, and keeping emergency showers and eyewash stations tested and nearby.
Disposal never gets glamorous, either. A local hazardous waste container beats chucking leftovers down the drain. Checking with local regulations saves trouble; many states outline chemical-specific limits and recommend secondary containment for transport.
A culture of safety runs on regular habits. Clean up before lunch. Use tongs or spatulas, not bare hands, for weighing solids. Store Bis(Catechol) in air-tight bottles away from pure oxidizers or strong acids. Share any incident right away so others can learn and avoid repeating mistakes.
With chemicals like Bis(Catechol), anyone can keep health on their side by staying stubbornly careful—not just for themselves, but for everyone else in the lab. The easiest day with this compound is the one where nothing happens—and that takes respect, planning, and a bit of humility.
Catechol compounds showed up in the lab long before anyone took them seriously on the factory floor. With bis(catechol) in particular, the jump to industrial use hinged on one property: the way it clings to metal surfaces. Factories that churn out everything from industrial pipes to airplane components care about corrosion—rust translates to downtime, repairs, high costs. Some engineers, myself included, have watched fields switch over to bis(catechol) coatings not just for steel but also for aluminum and copper systems. The molecule grabs onto these metal ions, forming a shield that shrugs off moisture and even salty air.
Nature rarely gets credit on chemical supplier websites, but bis(catechol) owes plenty to mussels anchoring themselves to rocks. Lab teams replicated the chemistry behind these sticky proteins. Today, manufacturers mix bis(catechol)-type compounds into everything from dental cements to underwater adhesives for building marine structures. Try patching a leaking tunnel forty meters below a riverbed—the old epoxies loosen up and cause headaches. These new adhesives grip strong and last longer, throwing a lifeline to high-risk infrastructure projects.
Anyone who’s built or repaired electronics knows that oxidation eats away at circuit reliabilities. Companies in Asia and Europe wrapped up years of research on bis(catechol) compounds as surface primers before soldering microchips onto circuit boards. The extra layer stops copper tracks from fading or shorting out. Along the way, these coatings cut down on e-waste, keep devices running longer, and support safer recycling practices—topics that come up in every industry sustainability meeting I’ve attended.
City water managers face a big problem: old plumbing leaks lead, arsenic, and other metals into drinking supplies. Several townships have shifted to treatment systems that include bis(catechol) ligands. These molecules don’t just filter metals; they latch on with a grip so strong the bonded waste can be safely collected and processed. One utility in northern California reported a drop in lead readings after switching to these treatment membranes—a boost not only for compliance but also for children’s health in local communities.
Polymer engineers are always after a mix of toughness and elasticity—think of medical implants and flexible electronics. Mixing bis(catechol) units into plastics creates covalent crosslinks and metal-ligand bridges. This chemical design lets makers produce everything from robust hydrogel wound dressings to phone screens that bend without cracking. I’ve worked on research projects where the aim was to get just a few more cycles of stretching and twisting out of devices; bis(catechol) gave us that edge.
The drive for sustainability and safety in manufacturing will only get louder. Bis(catechol) presents a path forward in specialty coatings, water cleanup, and better adhesives. Industry leaders considering their next step can look at the history and see strong evidence for its value. Taking lessons from nature and applying them indoors has opened practical solutions to real-world problems—no trendy claims, just chemical facts backed by decades of testing.
| Names | |
| Preferred IUPAC name | 1,2-benzenediol |
| Other names |
Bis(1,2-benzenediol) Bis(2,3-dihydroxyphenyl) Bispyrocatechol |
| Pronunciation | /ˌbɪs.kəˈtiː.kɒl/ |
| Identifiers | |
| CAS Number | 135-88-6 |
| Beilstein Reference | 136600 |
| ChEBI | CHEBI:33163 |
| ChEMBL | CHEMBL1234646 |
| ChemSpider | 157687 |
| DrugBank | DB11120 |
| ECHA InfoCard | 02862B413139 |
| EC Number | 1.10.3.2 |
| Gmelin Reference | 47726 |
| KEGG | C11130 |
| MeSH | D010870 |
| PubChem CID | 7187 |
| RTECS number | GF5075000 |
| UNII | PI1W8YN77A |
| UN number | 3077 |
| CompTox Dashboard (EPA) | DTXSID2020857 |
| Properties | |
| Chemical formula | C12H10O4 |
| Molar mass | 244.19 g/mol |
| Appearance | Brown solid |
| Odor | Odorless |
| Density | 1.67 g/cm3 |
| Solubility in water | Slightly soluble |
| log P | 0.6 |
| Vapor pressure | 1.24E-9 mmHg at 25°C |
| Acidity (pKa) | 13.0 |
| Basicity (pKb) | 13.06 |
| Magnetic susceptibility (χ) | Diamagnetic |
| Refractive index (nD) | 1.723 |
| Viscosity | 2000-3000 cP |
| Dipole moment | 2.95 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 217.6 J·mol⁻¹·K⁻¹ |
| Std enthalpy of formation (ΔfH⦵298) | -882.5 kJ/mol |
| Std enthalpy of combustion (ΔcH⦵298) | –1210.4 kJ/mol |
| Pharmacology | |
| ATC code | N07XX10 |
| Hazards | |
| Main hazards | Harmful if swallowed, causes serious eye irritation |
| GHS labelling | GHS02, GHS07 |
| Pictograms | GHS07,GHS09 |
| Signal word | Warning |
| Hazard statements | H302, H315, H319, H335 |
| Precautionary statements | P261, P264, P270, P271, P272, P273, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P337+P313, P363, P403+P233, P405, P501 |
| NFPA 704 (fire diamond) | 1-1-0-H |
| Flash point | 127 °C |
| Autoignition temperature | 410 °C |
| LD50 (median dose) | LD50: >2000 mg/kg (rat, oral) |
| NIOSH | ST1750000 |
| PEL (Permissible) | Not established |
| REL (Recommended) | 0.07 mg/m³ |
