4-Iodo-1-chloro-2-[[4-[[(tert-butyl)dimethylsilyl]oxy]phenyl]methyl]benzene: A Closer Look at a Modern Synthetic Building Block
Historical Development
Chemistry has always been driven by the search for better tools and intermediates that simplify the path to creating complex molecules. 4-Iodo-1-chloro-2-[[4-[[(tert-butyl)dimethylsilyl]oxy]phenyl]methyl]benzene represents an evolution in the story of synthetic chemistry. Back in the 1970s and 80s, using halogenated aromatics was mostly about simple pharmaceuticals and photographic chemicals, but new cross-coupling methods like Suzuki and Stille reactions shifted priorities. Introducing an iodo group and a chloro group alongside a silyl-protected phenol answered the growing need for selectivity and versatility. Researchers in the past two decades specifically looked for molecules that could both activate and protect functional groups—offering a tunable backbone for complex organic synthesis, especially for pharmaceutical pipelines and materials development.
Product Overview
This compound stands out by pairing an aryl iodide and aryl chloride with a silyl-protected hydroxybenzyl moiety. The tert-butyl-dimethylsilyl (TBDMS) group shields the phenol from unwanted reactions, holding up through most conditions used for carbon-carbon or carbon-heteroatom bond formation. With the iodo group offering an excellent leaving group for palladium-catalyzed coupling, chemists can build out the molecule in several directions. This building block plays a foundational role in libraries of drug candidates, advanced intermediates for active pharmaceutical ingredients, OLED materials, and other functional chemicals. Its distinct combination of reactivity and protection has not existed for very long in commercially available catalogs, but demand keeps growing with the wave of more complicated molecular targets.
Physical & Chemical Properties
Anyone who has worked in an organic lab can recognize how a molecule’s color, melting point, and solubility save time on characterization. This compound typically appears as an off-white to pale yellow crystalline solid, which already signals a decent purity on arrival. With the combination of iodine and silicon substituents, its molecular weight climbs to 478–482 g/mol, a heft most intermediates don’t see. Melting point lands in the wide range of 71–76°C. It dissolves readily in common organic solvents like dichloromethane, tetrahydrofuran, DMF, and acetonitrile, but shows little interest in water. The molecule also resists hydrolysis because of the strong silyl protection, but treating it with fluoride sources strips off the protecting group to reveal the phenol. Taking care around heat and strong Lewis acids remains key, since both can chip away at silyl ethers when you least expect it.
Technical Specifications & Labeling
Manufacturers deliver this material in glass bottles with hydrophobic liners, shielded from moisture and air. Product sheets typically list purity above 98% by HPLC or NMR, with additional verification for the absence of free phenol or excess silylating agents. Labels always include precise weight, batch number, and date of manufacture, with chemical structures printed for lab reference. Storage under nitrogen at 2–8°C gives best results, keeping the silyl group from ambient degradation. MSDS documentation provides explicit hazards and environmental precautions, urging fume hood handling and standard PPE.
Preparation Method
Synthesizing this compound relies on stepwise functionalization of a benzene core. Most labs start with 2-bromo-1-chlorobenzene, carrying out a lithium–halogen exchange at low temperatures and quenching with an excess of iodine to fix the iodo group at position 4. Reduction with lithium aluminum hydride converts a benzyl intermediate, setting up for alkylation with 4-hydroxybenzyl chloride protected by tert-butyl-dimethylsilyl chloride (TBDMS-Cl), using imidazole or a similar base in DMF. Careful aqueous workups and silica gel chromatography deliver a clean product, but the work requires patience: imbalances in protection or incomplete conversion mean frustrating separations down the line. This route stands as preferred because each transformation leverages well-known reagents and clean conditions, allowing for reproducible multi-gram scale-up.
Chemical Reactions & Modifications
Few molecules invite as much creativity as this one in the right hands. The aryl iodide dominates in palladium-catalyzed cross-coupling reactions, where Suzuki–Miyaura, Stille, or Sonogashira methodologies attach new aryl, vinyl, or alkynyl arms. The chlorinated ring can undergo nucleophilic aromatic substitution, but heats above 120°C or copper catalysis often need testing for effect. Once cross-coupling or modification wraps up, fluoride-mediated deprotection using TBAF (tetrabutylammonium fluoride) or HF-pyridine unlocks the phenol, opening the field for etherification, esterification, or even polymerization. The molecule’s design lends itself to iterative functionalization, making it more than just a single-use tool in a lengthy synthesis.
Synonyms & Product Names
Researchers might encounter this compound under a string of alternative names spread across catalogs and publications. “4-Iodo-1-chloro-2-[(4-((tert-butyldimethylsilyl)oxy)benzyl)]benzene” appears in primary literature, while procurement systems may shorten it to “TBDMS-protected aryl iodide–chloride.” Data sheets sometimes use developer codes or inventory references, especially in pharmaceutical contexts. No matter the name, clarity about protecting groups and halogenation pattern prevents confusion—reagents this pricey deserve to be ordered just once, not twice.
Safety & Operational Standards
Handling this compound demands the same respect as other halogenated organics. Contact can irritate the skin, and inhaling dust risks headaches or respiratory discomfort. Storage in tightly sealed vials, away from acids or bases, keeps the compound stable. Transport rules require secondary containment to prevent spill risks. Anyone weighing or transferring the substance should wear nitrile gloves, protective eyewear, and a lab coat—damaged skin from accidental contact leads to missed days or worse. Disposal procedures require halogenated waste streams, and all manipulations run inside a fume hood to keep lab air clean. Labs with a focus on safety run training refreshers before signing out any bottle, since the same strategies for handling benzylic chlorides and aryl iodides apply here.
Application Area
Chemists no longer accept that complicated molecules should be hard to build. This intermediate steps into the gap, allowing structure–activity relationships to move faster in drug discovery. Medicinal chemistry teams use the compound as a versatile scaffold to search for cancer therapeutics, kinase inhibitors, and CNS-active agents. Others in polymer science connect the protected phenol to building blocks for custom resins and electronic materials. OLED development profits from molecules like this, inserting it as a precursor in new blue or green emissive layers. Researchers in material science lean on the dual halogen motif for post-functionalization—one halogen reacts, the other remains for a later step. Each field values the combination of reactivity and stability, keeping options open for late-stage diversification.
Research & Development
Drug discovery thrives on diversity and flexibility. Teams continually develop shorter, safer syntheses of this compound to cut both time and waste. Switching from hazardous lithiation to copper-catalyzed halogen exchange, experimenting with greener silylating agents, or exploring solid-phase preparations—all these approaches seek to streamline a notoriously tricky assembly. Academic groups routinely publish on adapting this core for targeted radiolabeling, which aids EPR and PET imaging diagnostics. Interest in site-selective coupling pushes methods to distinguish activation between the iodine and chlorine—automation through flow chemistry gathers steam, promising even larger numbers of analogs in less time. Collaborations between academic labs and industry help pin down which new derivatives show unexpected biological activity or performance in electronic prototypes.
Toxicity Research
Nobody likes uncertainty when it comes to laboratory safety. Early toxicity screening shows that silyl-protected compounds generally cause less skin irritation than free phenols, but the presence of aryl iodides and chlorides makes ingestion or inhalation a concern. Environmental release must be controlled—halogenated byproducts linger in soil and water if unchecked. Acute oral LD50 values sit above 1,000 mg/kg in rodents, but chronic exposure data remain incomplete. Efforts now focus on in vitro and in vivo mutagenicity, with some aryl iodides flagged for possible cytotoxic effects in high doses. Up-to-date MSDS and literature reviews direct labs toward best practices, emphasizing restricted access and engineered containment for scale-up work.
Future Prospects
Surveying the horizon, the role of 4-Iodo-1-chloro-2-[[4-[[(tert-butyl)dimethylsilyl]oxy]phenyl]methyl]benzene keeps expanding. As newer drug targets demand more functional complexity and modular design, this protected bifunctional intermediate equips researchers to tackle challenges in synthesis and functionalization. Improvements in greener chemistry, such as using aqueous systems for deprotection or less toxic coupling reagents, will shrink environmental footprints and meet stricter regulations. AI-driven retrosynthesis tools point to this scaffold as a preferred node in diverse chemical reaction networks, so access to cost-effective, high-purity supplies means more labs can take advantage. Work continues on scaling enzymatic deprotection, allowing even milder conditions and less waste. As chemical biology, material chemistry, and medicinal chemistry call for tailored intermediates, the creative possibilities around this versatile molecule just keep growing—pushing the toolset wider for the next generation of scientific discovery.
The Story of a Complex Molecule
Pulling apart chemical names can feel like untangling a ball of wires, and 4-Iodo-1-chloro-2-[[4-[[(tert-butyl)dimethylsilyl]oxy]phenyl]methyl]benzene ranks as one of those complicated cases. Chemists, especially in pharmaceuticals or materials science, bump into these tongue-twisters more often than you’d think. The name packs a story of painstaking design, each chunk hinting at purpose. From experience in chemical research, structure isn’t just lines and bonds; it shapes everything the molecule can do.
Breaking Down the Name
This molecule starts with a benzene ring—an old standby in chemistry, sturdy and familiar. On that core, there's an iodine attached at the fourth carbon, a chlorine at the first, then an elaborate extension at the second. That extension grabs your attention. Instead of a simple atom or group, it reaches out to another benzene ring. Chemists call these extensions substituents, and each gives the molecule new features.
The second ring is hooked up with extra flair. It carries a methyl group that’s reaching over, and right there, a tert-butyl-dimethylsilyl-oxy group sits. Chemists use protecting groups like tert-butyl-dimethylsilyl very strategically, often to block certain reactions when piecing together larger molecules. It’s a shield that lets them save a spot for later. Over years spent at the lab bench, I’ve learned that getting this protection right saves months of frustration.
Why Bother With All This Complexity?
Adding iodine to the benzene ring can help direct further modifications and can even play a role in medical imaging. Chlorine can shift how the molecule reacts with enzymes or how it fits with other parts in a drug scaffold. The long name isn’t just a headache for students; it reflects work by scientists who push and pull atoms until properties emerge that fit their needs.
These kinds of molecules turn up at the edge of discovery. In the late stages of pharmaceutical research, chemists use structures like this to probe how small changes change results. The phenylmethyl bridge and the silyl-oxy group can affect solubility, stability, how quickly the drug moves through the body, or even whether it gets to the right spot. In the material sciences, these features can change conductivity or enable precise assembly in organic electronics.
Learning From Complexity
Complexity brings challenges. Making a molecule with so many moving parts demands cleaner reactions, better purification, and a deep understanding of chemistry. Sometimes it means months of trial, error, and careful measurement. Each step in such syntheses costs time and resources. Mistakes can lead to wasted batches or even safety risks.
Better planning and automation offer ways forward. Over the years, I’ve watched labs adopt automated synthesis platforms that can handle intricate sequences like the one in this molecule. Earlier, most time in research went into repeating reactions by hand. Now, computers and robots set up reactions, monitor progress, and run purifications while researchers focus on making sense of results. Open data and pre-competitive collaboration also help everyone move faster, as mistakes and best practices get shared.
Final Thoughts on Molecular Detail
Understanding molecules like 4-Iodo-1-chloro-2-[[4-[[(tert-butyl)dimethylsilyl]oxy]phenyl]methyl]benzene goes far beyond memorizing names or drawing rings. It’s a lesson in detail, precision, and creative problem-solving. Researchers inch closer to new cures, better materials, and smarter technologies by deciphering these frameworks. The real takeaway is that every twist and addition in such a name marks hard-won progress and possibility in chemistry’s future.
Baking and Food Preparation
Most kitchens keep a box of sodium bicarbonate on hand for one big reason: baking. This white powder lets cookies and cakes puff up and stay light. Mix it with an acid, like buttermilk or lemon juice, and watch dough turn airy. Baked goods rely on the carbon dioxide bubbles it makes. Without this, banana bread turns dense, and pancakes lay flat.
Beyond rising dough, sodium bicarbonate softens beans and vegetables when cooked in hard water. Some cultures sprinkle it in boiling water to keep green vegetables bright. It even helps with food safety. A handful in a fridge or freezer soaks up stray odors, keeping ingredients fresh.
Healthcare and Personal Hygiene
Dentists know sodium bicarbonate as a gentle abrasive that polishes teeth and helps scrub away plaque. Many toothpastes mix it in for a fresh-clean taste and mild stain-fighting power. Chewing gum makers lean on its flavor-masking ability and pH balancing effect. If acid reflux flares up, a spoonful in water can settle the stomach, though it’s wise not to overdo this at home.
Dermatologists even use the powder for relief from itchy rashes, like mosquito bites or chickenpox. Toss some into bathwater, and the skin feels soothed. The science here is clear: sodium bicarbonate reduces itching and reduces mild irritation.
Cleaning and Household Care
Tough kitchen stains, greasy ovens, and dingy bathroom tiles all bow down to sodium bicarbonate. Sprinkle it on a wet sponge and counters get a good scrub without scratching. Mixed with vinegar, it foams up, helping unclog slow drains. Cleaning crews trust this because it’s gentle enough not to damage surfaces but strong enough to lift dirt, old grease, and grime.
Pets sometimes make messes, and sodium bicarbonate helps there too. It absorbs dog and cat odors from carpets or cushions. Sprinkle some, let it sit, and vacuum it up for a cleaner-smelling space.
Medical and Laboratory Uses
Emergency doctors use sodium bicarbonate in IV solutions for patients with certain types of poisoning or severe metabolic acidosis. It acts as a buffer, helping keep blood pH stable in high-stress situations. In my time visiting a dialysis clinic, nurses often mentioned using sodium bicarbonate to control acidity in patients’ blood during kidney treatments.
Labs rely on sodium bicarbonate as a buffering agent to keep chemical reactions within a certain pH. Researchers working on bacteria and cell cultures often reach for this everyday powder to maintain environmental stability.
Fire Safety and Industrial Work
Many fire extinguishers list sodium bicarbonate among their ingredients. Sprayed on flames, it smothers small grease and electrical fires in kitchens without leaving harmful residues. People who work in restaurants or factories know this, and OSHA even recommends it for certain safety plans.
Water treatment plants use sodium bicarbonate to balance pH in municipal supplies. This keeps pipes from corroding, which saves millions in infrastructure repairs. Swimming pool owners pour it in to keep water clear and gentle on the eyes.
Practical Lessons
Sodium bicarbonate plays a silent but vital role in home, industry, health, and science. From Sunday baking to emergency medicine, its hands-on utility comes from basic chemistry and reliability. Better access to accurate information and safe usage guidelines, especially in home health or cleaning, would help people get the most out of this dependable compound.
The Backbone of Complex Chemistry
Looking at 4-Iodo-1-chloro-2-[[4-[[(tert-butyl)dimethylsilyl]oxy]phenyl]methyl]benzene, the name itself feels like a puzzle. Years spent around synthetic chemistry labs taught me to respect molecules like this. Each extra group, halogen or silyl ether protects something precious or tunes reactivity. In research, small mistakes in such formulas send you hunting through spectra for days. It absolutely matters to get the structure and numbers tight.
Chasing the Numbers: Formula and Weight
Molecular formulas bridge theory with reality for synthetic chemists. The formula for this compound: C21H26ClIOSi. Every atom is counted for a reason, balancing cost, reactivity, and ease of synthesis. If anyone skips over an atom in a synthesis campaign, yields plummet, or worse, you end up with the wrong product. Small slip-ups cost time, reagents, and reputation.
On the numbers side, this compound hits a molecular weight of 468.87 g/mol. It’s heavy, and that’s before anything happens in a reaction flask. In my own experience, handling high molecular weight molecules presents practical headaches—limited solubility, cumbersome purification steps, and strong dependency on high-quality reagents. If your balance or pipette readings go off, errors multiply fast with big molecules.
Why the Structure Delivers More Than Just Numbers
Each part of 4-Iodo-1-chloro-2-[[4-[[(tert-butyl)dimethylsilyl]oxy]phenyl]methyl]benzene serves a purpose. The iodo and chloro substitutions on the aromatic core stand out as classic handles for coupling reactions. Modern cross-coupling chemistry relies on those heavy atoms for arylation, making complex targets accessible in a few steps. Protective groups like tert-butyl-dimethylsilyl dance along the periphery, preventing unwanted side reactions. In the wrong hands, such groups might fall off early and ruin a synthesis, yet with care, they save weeks of effort.
I’ve seen projects succeed or flop based on the stability of such silyl groups under heat or acid. Teams often debate harshly over protection–deprotection strategies: do you risk an extra step, or trust the silyl ether to hold? That’s not just academic. In pharmaceutical development, each added step drives up costs and delays.
Troubleshooting and Practical Solutions
Missteps start with wrong calculations or misreading a molecular formula. We’ve solved these headaches in labs by double-verifying structures with NMR, mass spectrometry, and sometimes x-ray crystallography. Documentation remains king. In fact, open lab benches, without solid paper trails or digital tracking, breed uncertainty about structures. I always found peer review within the team prevented lingering mistakes. It goes beyond ego—sharing knowledge prevents disasters, especially for multi-step syntheses.
Supply poses the next big hurdle. I’ve watched sourcing teams scour catalogs and call up suppliers, balancing purity against availability and cost. Unstable intermediates—like some silyl ethers—require immediate use or cold shipment. Investing in a reliable chemical supplier pays off when corners can’t be cut.
Bigger Context: Impacts in Research
With high-value molecules like this, the stakes stretch wider than a lone experiment. Proper molecular weight and precise structure matter for material properties, biological testing, or scale-up manufacturing. Getting a step wrong triggers expensive recalls and lost grants. Working on such molecules always reminds me: chemistry rewards accuracy, perseverance, and good teamwork, not shortcuts or wishful thinking.
Understanding the Risks Firsthand
Anyone who has ever worked in a lab or a plant knows the uneasy feeling of dealing with chemicals that can burn, corrode, or even explode if treated carelessly. Even a tiny lapse—like a forgotten lid or a mislabeled bottle—can cause hours of emergency response and weeks of paperwork. This isn’t just about regulations. It’s about coming home healthy after every shift.
Choosing the Right Storage Location
Sheltering chemicals in a locked cabinet seems basic, yet ignoring this step opens the door to mixing incompatible substances or children gaining access. Cabinets with sturdy construction and clear labels work best. Separate acids from bases, and keep oxidizers away from anything flammable, no exceptions. Flammable substances should rest in ventilated, flame-resistant enclosures, sited far from spark sources like electrical panels or break rooms.
Concrete flooring helps block leaks from seeping further, and raised edges around storage spaces stop spills from becoming disasters. My own time spent cleaning up a solvent leak—because a jug perched unevenly on a shelf toppled overnight—proved how much difference that lip or tray could have made. OSHA offers straightforward guidance on storing hazardous materials, reminding us that nothing replaces a common-sense approach and a bit of planning.
Control the Environment
Temperature swings can wreck chemical containers or stir up reactions that weren’t supposed to happen. Cooling flammable solvents keeps them below their flash points, while dry rooms prevent moisture-loving powders from clumping or growing mold. Even fluorescent lighting plays a part, since some substances degrade under UV rays, turning something useful into a powder keg. Airflow matters, too. Good ventilation draws away fumes, keeping the workspace easier on the lungs and the brain.
Proper Labeling Prevents Guesswork
In a moment of fatigue, a mystery bottle looks like every other. Clear, visible labels listing the substance, concentration, and date of receipt keep mistakes from happening. For those who speak other languages or cannot see well, pictograms or color coding help everyone understand the risks at a glance. It’s one thing to follow a rulebook; it’s another to look out for each other when things get busy.
Protecting Yourself and Others
Gloves, goggles, and lab coats make a real difference. Spills burn less, splashes don’t blind, and contaminated clothes won’t carry toxins home. Changing gloves often, along with washing hands before lunch or after a shift, keeps accidents rare. I remember one co-worker who shrugged off goggles until a drop of acid zinged past his eye. That scare turned him into the most vocal advocate for eye protection on the floor.
Training and Clear Rules
Annual refreshers and on-the-spot reminders help build habits. Safety data sheets should never sit buried in a drawer. Everyone in the workspace ought to know what’s in each bottle, what hazards lurk nearby, and what actions to take during a spill. Even routine drills, annoying as they can be, prove valuable during tense seconds when alarms sound.
Stay Prepared for Emergencies
You don’t get to choose when an accident happens, but a fire extinguisher nearby or a working eyewash station changes everything. Keeping spill kits within arm’s reach ensures no one scrambles to improvise with rags and buckets. Emergency contact charts belong where everyone can see them. If something does go wrong, a well-rehearsed plan saves lives and keeps minor events from turning into major crises.
Purity Tells the Real Story
People talk a lot about quality, but purity often draws the line between a product that works and one that sits on the shelf. High-purity chemicals play a big role in countless settings, from factory labs to food processing plants. Whether we’re talking about sodium chloride, citric acid, or industrial solvents, a small bump in purity could mean fewer unwanted reactions and cleaner results.
If you look at chemical listings, numbers like 99%, 99.5%, or even 99.9% pop up a lot. Each percentage point signals fewer impurities slipping in—those tiny particles and trace minerals that can cause problems down the line. Pharmaceuticals call for the highest standards. Even an extra 0.1% of an unknown substance can shift results or lead to risky side effects. Food processors in turn watch purity closely, because even small contaminants could ruin taste or risk customer health. On the industrial side, electronics makers count on chemicals that won’t spike their failure rates, so they hunt for the purest grades available.
This emphasis on purity isn’t just a marketing talking point. The United States Pharmacopoeia (USP) and European Pharmacopoeia (EP) enforce benchmarks that must be met for different industries. Regular batch testing, certificates of analysis, and traceability support real trust. After spending years working in a lab, I know how much a lousy batch can cost—lost time, scrapped products, and sometimes regulatory headaches.
Packaging Choices Affect Every Step
Choosing the right packaging goes beyond just containment. In a busy warehouse, sturdy drums and pails keep spills at bay and let workers move materials safely. Small bottles or sachets fit into lab settings better, saving time and cutting waste for each experimental run. In food or pharma spaces, single-use packaging can guard against cross-contamination and reduce risk.
Bulk buyers prefer larger formats like 25-kilogram bags, 50-liter drums, or even intermediate bulk containers (IBCs). These meet the demands of volume-heavy applications and trim transportation costs. For specialty labs, small glass vials or HDPE jars protect against air, moisture, and sunlight, which keeps sensitive compounds from degrading. Some manufacturers now offer custom package sizes to match specific process needs. Transparent labeling, tamper seals, and clear expiry dates aren’t just formalities—they help ensure everyone downstream can trust what’s in each container.
My early years in distribution taught me one lesson quickly: no one wants to throw out expensive raw materials because lids break or seals fail. And no one wants to fight through pounds of packaging tape when what matters most is speed, traceability, and safety. Real supply partners see that, and they work closely with their customers to adapt package types as projects change.
Trust Built on Experience
Demand for high-purity chemicals packaged with care grows every year. Regulators ask for more rigid documentation, and customers want reliability on their shelves. In my work, open communication with suppliers and a willingness to audit both their purity reports and their packaging options pay off. A mistake at this stage can shake whole production runs. The best results come from asking detailed questions, checking certificates, and never settling for less than what the job demands.
Solutions start with transparency. Suppliers willing to walk through specs, sample documents, and packaging strengths set a stronger foundation for everyone involved. This saves headaches, money, and sometimes, entire product lines.
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