|
HS Code |
133969 |
| Iupac Name | 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile |
| Molecular Formula | C12H15BN2O2 |
| Molecular Weight | 230.08 |
| Cas Number | 1171233-72-5 |
| Appearance | White to off-white solid |
| Melting Point | 87-90°C |
| Solubility | Soluble in organic solvents such as DMSO, DMF, and dichloromethane |
| Smiles | CC1(C)OB(B2=CC(=NC=C2)C#N)OC1(C)C |
| Inchi | InChI=1S/C12H15BN2O2/c1-11(2)16-13(17-12(3)4)10-6-9(8-15)7-14-5-10/h5-7,11-12H,1-4H3 |
| Purity | Typically ≥95% |
| Storage Conditions | Store at 2-8°C, keep container tightly closed |
| Hazard Statements | May cause irritation to respiratory tract, skin and eyes |
As an accredited 2-Pyridinecarbonitrile,4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | The chemical is packaged in a 5-gram amber glass bottle with a secure screw cap and tamper-evident seal, labeled for laboratory use. |
| Container Loading (20′ FCL) | Container Loading (20′ FCL) for 2-Pyridinecarbonitrile, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- ensures secure, bulk packaging and safe global transport. |
| Shipping | 2-Pyridinecarbonitrile, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- is shipped in tightly sealed containers, protected from light and moisture. It is transported at ambient temperature unless otherwise specified, and handled according to standard chemical safety protocols. Proper labeling and documentation are ensured for safe, regulatory-compliant delivery. |
| Storage | 2-Pyridinecarbonitrile, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- should be stored in a cool, dry, and well-ventilated area, away from moisture and incompatible substances such as strong oxidizers. Keep the container tightly closed and protect from light. Store under inert atmosphere, such as nitrogen or argon, to prevent decomposition. Follow standard laboratory safety procedures when handling and storing this chemical. |
| Shelf Life | Shelf life of 2-Pyridinecarbonitrile, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl): Typically stable for 2 years if stored cool, dry, and protected from light. |
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Purity 98%: 2-Pyridinecarbonitrile,4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- with a purity of 98% is used in pharmaceutical synthesis, where it ensures high-yield coupling reactions. Molecular Weight 244.17 g/mol: 2-Pyridinecarbonitrile,4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- with a molecular weight of 244.17 g/mol is used in catalyst design, where it provides precision in stoichiometric calculations. Melting Point 147-149°C: 2-Pyridinecarbonitrile,4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- with a melting point of 147-149°C is used in material science research, where it permits controlled crystallization processes. Storage Stability -20°C: 2-Pyridinecarbonitrile,4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- with storage stability at -20°C is used in chemical libraries, where it provides extended shelf life and minimal degradation. Particle Size ≤20 µm: 2-Pyridinecarbonitrile,4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- with a particle size of ≤20 µm is used in high-throughput screening, where it ensures uniform suspension and reproducible assay results. |
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Producing 2-Pyridinecarbonitrile,4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, or simply the 4-boryl-2-cyanopyridine, calls for a recognition of how nuanced modern organic synthesis can be, especially as pharmaceutical and material science research continue to advance. For years, we’ve worked directly with medicinal chemistry teams who need this compound as a versatile building block for preparing heterocyclic scaffolds and for Suzuki-Miyaura coupling reactions. Understanding the expectations of bench chemists and process teams helps us prioritize features that matter: high purity, consistent particle characteristics, and reliable shipment.
Every batch of this boronic ester derivative relies on an air- and moisture-controlled setup. Our employees don’t just rely on the standard glass apparatus; they supplement routine tracking with in-process HPLC and NMR, confirming that the material matches its expected profile—pale solid, free-flowing, and stable for extended storage when kept dry and cool. The typical specification targets a purity above 98%, using GC, HPLC, and NMR authentication as routine, so that every container meets synthetic needs without surprise contaminants that might disrupt catalytic cycles.
The model designation our plant uses refers to the precise substitution: a cyano group on the 2-position of the pyridine ring, paired with a boronic ester on the 4-position. That orientation has crucial implications for many chemistry workflows, particularly for teams optimizing late-stage functionalization or seeking clean conversions in palladium- or nickel-catalyzed cross-couplings. By keeping the tetramethyl dioxaborolane protected boron, our product avoids rapid hydrolysis or boronic acid polymerization, which can otherwise complicate workup and purification.
Mid-sized pharmaceutical developers, research labs, and catalyst evaluation groups approach us often because this compound fits into a gap left by more common arylboronic acids and esters. The cyano-pyridine scaffold shows up repeatedly in clinical candidates, energy storage materials, and advanced polymer design. We see our product most often deployed in Suzuki-style couplings, where chemists form carbon-carbon bonds with aryl halides or other boron derivatives. Occasionally, small specialty API batches or pilot-scale projects focus on introducing fluorines or other groups adjacent to the boron, relying on this core intermediate. Our customers often report that the dioxaborolane protection unlocks more reliable reactivity and storage profiles versus plain boronic acids, where instability or premature deboronation would otherwise cause losses.
Academics transitioning syntheses from milligram to gram quantities have mentioned the value of our purification and formulation choices. Most off-the-shelf material with unknown hydration levels, variable tautomer ratios, or unassessed trace metallics can lead to irreproducible outcomes in critical assays. On the other hand, we field calls from process engineers seeking notification about any change in the dioxaborolane batch or synthetic precursor, which only underscores the importance of transparency and consistency at the manufacturer’s level. It’s not uncommon for a project to pivot from an acid chloride intermediate to a boronic ester route, chasing yields, green chemistry credentials, or patent circumvention—and 4-boryl-2-cyanopyridine brings flexibility in those decisions.
We’ve tracked growing interest in borylated heterocycles over the last decade. The 2-pyridinecarbonitrile skeleton, compared to unsubstituted or 3- or 5-substituted analogs, brings greater electronic control and more predictable site selectivity in palladium- and copper-catalyzed procedures. Our experience shows that this product flows easier, handles less hygroscopically, and dissolves more predictably in common solvents like DMF, dioxane, and THF, compared to many boronic acids.
Some labs have tried alternatives such as potassium trifluoroborates or plain arylboronic acids. In several campaigns, we’ve seen clear experimental benefits for the dioxaborolane variant—its low volatility, good shelf stability, and manageable melting range let chemists stock it in dryboxes or even at room temperature for weeks. Material loss from accidental hydrolysis decreases noticeably. At scale, these storage and handling characteristics translate to fewer waste drums, less volatile loss, and more robust process control.
Practical synthesis rarely proceeds without hitches—anyone on a production floor will admit that. Unwanted byproducts, residual halides, and water traces can turn a promising arylboronic acid coupling into a failed run. That’s why our team spends time purifying not only the final compound, but also crucial intermediates and solvents, using Karl Fischer titration and rigorous drying protocols. NMR and HPLC checks run on every output drum. We’ve had several customers reach out after success with our material in automated synthesizer platforms, noting fewer out-of-spec events compared to procurement from trading companies or resellers.
One chemist’s nightmare, managing batch-to-batch drift, comes up less often with our dioxaborolane-protected pyridinecarbonitrile, given the relative inertness and lack of clumping or caking over time. In our plant, the environmental and safety protocols guide every handling step, since boronic esters and nitrile groups both come with their risks. Staff work behind low-humidity environments and take special precautions grounding glassware to avoid static ignition, especially when working with fine powders.
Daily, we see extensive use of this boronic ester in cross-coupling steps that require clean, controlled addition—run-of-the-mill boronic acids don’t always hit the mark, especially where functional group compatibility matters. Medicinal chemists choosing this specific 4-boryl-2-cyanopyridine report good conversion rates with standard ligands, even challenging electron-poor or crowded systems. The electrophilicity of the cyano group can sometimes raise flags about leaving group exchange or catalyst poisoning, but in the hands of careful researchers, those hurdles get managed with intelligent ligand and base selection.
Material science researchers approach the compound with a different mindset. They value its compatibility with backbones that tolerate limited water and air exposure—helpful when constructing sensors, OLED components, or polymer precursors. The combination of cyano, pyridyl, and boronic ester reactivity creates opportunities to tune both physical properties and electronic structures.
Scale-up projects often strain any synthetic chemist’s workflow, but dioxaborolane derivatives like this offer clear support. Our in-house trials confirm manageable exotherms, reliable filterability, and compatibility with both batch and flow conditions. During routine kilogram upgrades, we spot better overall yields than with plain boronic acids or pinacol boronate alternatives, often due to reduced bulk hydrolysis and improved filtration.
For customers shipping internationally, the thermal stability and regulatory profile have additional implications. This compound avoids some of the most stringent shipping categories, lowering hazard management costs and regulatory overhead. Our team ships it without special atmospheric packaging where regulations permit, but for sensitive users, we offer vacuum-sealed or nitrogen-filled drums upon request.
Borylated pyridines span a broad performance range. Some preparations deliver inconsistent particle size, excess carrier solvent, or unknown polymorphs—issues that frustrate both research and manufacturing. Our process aims to eliminate trace halogens and metallic impurities, which can suppress catalyst performance or introduce troublesome regulatory flags. Where some competitors rely on less rigorous crystallization steps, our plant schedules HPLC-based fractionation and multiple solvent washes on every batch.
Plain 2-cyanopyridine lacks the modularity required for downstream transformations, while its 4-halo or 4-amino derivatives carry different reactivity tables. Other boron variants, such as pinacol, can struggle to match our dioxaborolane’s shelf life or resistance to dimerization. We’ve tracked purity retention during storage and found minimal degradation even after several months in dry, ambient storage, unlike some alternatives that degrade or pick up moisture unpredictably.
We don’t produce chemicals in a vacuum. Feedback loops with users guide every improvement. Recent pharma syntheses reported over 95% isolated coupling yields, attributable in part to the minimized water and halide levels in our batches. Material scientists provided notes for improved grind size on subsequent lots, so our team invested in precision milling and customized screening to meet their demands.
In consulting with academic partners, we’ve dug into bottlenecks with process transfer and scale jumps. Often, a problem tracks back to the handling behavior of the boron component, be it clumping, stuck filtration, or outgassing during workup. Since switching to our material, some users shortened cycle times by hours, skipping laborious dry-downs that competing analogs require. Others highlighted reduced spectral impurities in LC-MS readouts—vital for process validation and patent submission.
No process stands still—regulatory norms tighten, customer expectations increase, and raw material suppliers sometimes shift slow. Pyridine derivatives, by their nature, require careful monitoring for nitrosamine and related impurities. Our analytical team keeps sample archives from every batch, running additional GC-MS checks as new future toxicity guidelines emerge. When potential trace impurity risks are flagged, we alert downstream customers and provide updated material safety profiles as standard practice.
Waste management sits high on our priority list. The boronic ester synthesis and subsequent purification create organics-rich aqueous and organic waste streams. We’ve upped investment in on-site recycling, moving to solvent recovery units and safer neutralization techniques, to avoid both regulatory headaches and environmental risk. Customers who tour our facility cite our transparency and willingness to field questions about every solvent jug and waste drum. In some cases, sharing purification approaches leads to collaborative improvements for both sides.
One technical bottleneck continues to be grain size control in large-batch crystallizations, which can impact subsequent filtration times. To address this, our R&D staff have trialed slower solvent addition, seeded crystallization, and temperature-gradient protocols. We share these tweaks with core users who regularly need high-throughput filtration or rapid-mixing and welcome feedback if unique issues arise.
Consistency creates trust, and trust creates repeat collaborations. As a manufacturer, we feel the responsibility to back our chemicals with direct communication, clear order fulfillment, and open technical support. Our shipping runs tightly scheduled; rush orders, though never stress-free, often matter for time-sensitive discovery teams or production campaigns with high-value milestones.
Supply chain interruptions—be they from geopolitical events, shipping bottlenecks, or raw material constraints—push us to deepen stock and maintain close liaison with all input suppliers. We keep rolling forecasts, double-check inventory, and regularly test held product lots to ensure no drift in quality.
Regulatory and practical requirements never stand still. Before launching any new batch of 2-pyridinecarbonitrile,4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, we consult with both in-house and independent toxicologists to validate safety and handling data. When new catalysis protocols emerge—such as ligandless or radical-based couplings—we test our product in those workflows and revise process notes accordingly.
Looking ahead, greener approaches for both boron group installation and pyridine nitrile formation are already under lab-scale evaluation. In practice, these sometimes translate to incremental efficiency gains, reduced waste, and tighter impurity profiles. Customers with specific solvent or process restrictions often challenge us to further minimize risk of cross-contamination or mixed solvent residue, which keeps our QC laboratory motivated and always improving.
Many users who’ve purchased from trading companies or third parties have shared stories of mixed batches, incomplete paperwork, or surprise shipping conditions. Direct manufacturing bypasses those complications. Our production teams own every step, from raw input to packed drum, so discrepancies get caught fast. Analytical snapshots from the production line map to every product ID, batch, and corresponding data sheet.
We see our relationship with customers as collaborative. Chemists with scale-up questions often request tailored drying protocols or custom packaging formats. By working directly with the lab that synthesizes and packs the chemical, those changes get enacted swiftly, without several layers of communication lag. This close connection helps both sides achieve efficiency, cost control, and, above all, reliability in daily research and production.
The landscape for modern chemical synthesis relies on ever more selective, efficient, and stable intermediates. This product, with its combination of cyano and boryl substitution on the pyridine ring, meets demand for advanced cross-coupling reagents while supporting the shift toward greener, more predictable chemistry. The dioxaborolane group offers enhanced stability, smooth purification, and fewer batch-to-batch surprises, whether the end use lies in drug research, polymer science, or specialty material development.
Our focus stays rooted in real-world batch production and daily laboratory problem solving. The ability to listen, respond, and adapt to evolving client requirements distinguishes direct manufacturers from less invested supply channels. Each improvement, whether from customer suggestion or internal innovation, feeds back into how we make, test, and deliver each container of this increasingly important boronic ester. The result grows not just with chemical sales, but with shared advances in science and industry.