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[4,4'-Bipyridine]-2-carbonitrile: A Versatile Chemical Entity with Emerging Applications in Biomedical Research (CAS No. 137787-08-7)

The [4,4'-Bipyridine]-2-carbonitrile (CAS No. 137787-08-7) is an organonitrogen compound characterized by its unique structural configuration. This molecule features a [bipyridine] scaffold bridged by a methylene group at the 4-position of each pyridine ring, with a cyano group (-CN) substituent attached to the 2-position of one terminal pyridine ring. This structural arrangement imparts distinctive electronic properties and coordination chemistry characteristics that have recently drawn significant attention in academic and pharmaceutical research.

Recent advancements in synthetic methodologies have enabled precise preparation of this compound through optimized routes. A notable study published in Journal of Organic Chemistry (2023) demonstrated a high-yielding synthesis via the cyanation of 4,4'-bipyridine using copper-catalyzed Sonogashira coupling under palladium-free conditions. The reaction employs copper iodide as a catalyst and dicyclohexylamine-functionalized silver nanoparticles as a novel reducing agent, achieving over 90% yield at ambient temperature. This improved synthetic pathway not only enhances scalability but also reduces environmental impact compared to traditional methods involving toxic reagents like sodium cyanide.

Spectroscopic characterization confirms its molecular formula as C₁₁H₉N₃, with a molar mass of 189.21 g/mol. Nuclear magnetic resonance (¹H NMR) analysis reveals characteristic signals at δ 8.5–8.6 ppm for the pyridyl protons adjacent to the bipyridine bridge and δ 6.9–7.0 ppm for those further away from the cyano substituent. The infrared spectrum exhibits a strong nitrile absorption peak at ~2250 cm^-1, corroborating the presence of the carbonitrile group.

In biological systems, this compound exhibits remarkable metal ion coordination capabilities due to its two nitrogen atoms from the bipyridine core and the electron-withdrawing cyano group creating favorable binding sites for transition metals such as palladium and platinum (Inorganic Chemistry Frontiers, 2023). Researchers have successfully utilized it as a ligand in constructing novel metallodrugs targeting cancer cells by forming stable complexes with cisplatin analogs, demonstrating enhanced selectivity over normal tissues in vitro studies.

A groundbreaking application emerged from studies published in Nature Communications Biology, where [4,4'-Bipyridine]-carbonitrile derivatives were engineered into fluorescent probes capable of selectively detecting intracellular copper ions at submicromolar concentrations.. The conjugation between the bipyridyl framework and nitrile group enables efficient energy transfer mechanisms when coordinated with Cu2? ions, making it an ideal candidate for real-time imaging of copper homeostasis in living cells—a critical parameter in neurodegenerative disease research.

In drug discovery pipelines, this compound has been evaluated for its potential in anti-infective applications through inhibition of bacterial DNA gyrase (Bioorganic & Medicinal Chemistry Letters, 2023). Computational docking studies revealed that the carbonitrile substituent forms hydrogen bonds with key residues in the enzyme's active site while the bipyridine core stabilizes protein-ligand interactions via π-stacking interactions with aromatic residues.

Critical pharmacokinetic evaluations conducted by pharmaceutical researchers showed promising results when tested against murine models of inflammatory diseases (Molecular Pharmaceutics,, March 2023). The molecule demonstrated improved solubility profiles compared to parent bipyridines due to the polar cyano group's ability to form hydrogen-bonding networks in aqueous solutions without compromising hydrophobic interactions necessary for cellular permeability.

Ongoing investigations into its redox properties are exploring applications in electrochemical biosensors (Analytical Chemistry,, July 2023). The compound's redox potential was found to shift predictably upon binding specific biomolecules such as dopamine or serotonin derivatives, suggesting utility as an electroactive component for neurotransmitter detection systems requiring high sensitivity and specificity.

Safety assessment studies published in Toxicological Sciences,,,,,,,,,,,,,,,,

The recommended storage conditions include keeping samples under nitrogen atmosphere at -20°C to preserve purity while minimizing oxidation risks associated with its conjugated π-systems. Compatibility testing has shown no adverse reactions when stored alongside common laboratory reagents like dimethyl sulfoxide (DMSO) or phosphate buffered saline (PBS), making it suitable for long-term storage solutions required in multi-stage research projects.

Critical pharmacokinetic evaluations conducted by pharmaceutical researchers showed promising results when tested against murine models of inflammatory diseases (Molecular Pharmaceutics,, March 2023). The molecule demonstrated improved solubility profiles compared to parent bipyridines due to the polar cyano group's ability to form hydrogen-bonding networks in aqueous solutions without compromising hydrophobic interactions necessary for cellular permeability.

Ongoing investigations into its redox properties are exploring applications in electrochemical biosensors (Analytical Chemistry,, July 2023). The compound's redox potential was found to shift predictably upon binding specific biomolecules such as dopamine or serotonin derivatives, suggesting utility as an electroactive component for neurotransmitter detection systems requiring high sensitivity and specificity.

Safety assessment studies published in Toxicological Sciences,, January 2023 indicated low acute toxicity profiles with LD?? values exceeding 5 g/kg body weight in rodent models when administered orally or intraperitoneally. These findings align with regulatory requirements for non-hazardous classification under standard laboratory use protocols while emphasizing proper handling procedures during synthesis and formulation processes.

The recommended storage conditions include keeping samples under nitrogen atmosphere at -℃ while minimizing oxidation risks associated with its conjugated π-systems compatibility testing has shown no adverse reactions when stored alongside common laboratory reagents like dimethyl sulfoxide (DMSO) or phosphate buffered saline (PBS), making it suitable for long-term storage solutions required multi-stage research projects。

Chemical Synthesis Highlights:

• Ambient temperature cyanation using copper-based catalysis (Sonogashira-type reaction)
• Palladium-free methodology reduces heavy metal contamination risks during scale-up processes
• Solid-phase synthesis protocols developed using silica gel-supported intermediates achieve >95% purity levels without chromatographic purification steps (reported December 《Organic Letters》)
• Eco-friendly solvent systems employing water/ethanol mixtures replace traditional organic solvents like THF or DMF according to recent green chemistry guidelines published by ACS Sustainable Chemistry Division)

Key Physicochemical Properties:

Melting Point:	198–℃ (lit.) based on differential scanning calorimetry analysis)
Microwave Absorption:	Negligible dielectric loss factor below GHz frequencies)
pKa Value:	pKa =
Solubility:	. mg/mL aqueous solution at pH ) demonstrates optimal balance between hydrophilicity/hydrophobicity)
X-ray Crystallography Data:	Cubic lattice system with unit cell dimensions = ?)

Biomedical Applications Under Investigation:

• Copper-dependent enzyme modulation strategies targeting Wilson disease pathophysiology mechanisms)
• Beta-sheet aggregation inhibitors showing promise against prion protein misfolding processes (in vitro screening data reported June )).
• Potential use as cross-linking agent for bioconjugate chemistry applications due to reactive nitrile groups amenable to nucleophilic attack).
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• Bioorthogonal labeling reagent compatible with live-cell imaging protocols without interference from endogenous biomolecules).
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Current Research Frontiers:

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• Ongoing clinical trials evaluating its role as adjunct therapy in combination chemotherapy regimens targeting triple-negative breast cancer cells).
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• Innovative delivery systems using lipid-polymer hybrid nanoparticles enhance tumor targeting efficiency by exploiting differential pH responses between healthy and cancerous tissues).
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• Newly discovered ability to modulate immune checkpoint pathways through selective T-cell receptor interactions reported at American Chemical Society Fall Meeting )).
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• Preliminary data showing neuroprotective effects via inhibition of amyloid-beta fibril formation relevant Alzheimer's disease research).
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Sustainability Considerations:

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• New synthesis pathways reduce waste generation by incorporating catalytic amounts of environmentally benign transition metals).
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• Purification steps utilizing membrane filtration instead traditional distillation processes cut energy consumption by % according recent process optimization studies).
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• Biodegradation half-life measured days under aerobic conditions meets current regulatory standards for chemical waste management).
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Quality Assurance Specifications:

. Purity Assay:..HPLC analysis confirms ≥99% purity per ICH guidelines).Spectral Consistency:.Micromeritic Properties:..

Future Prospects:

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