• 1. An approach to 7-aza-1-phosphanorbornane complexes: strain promoted rearrangement of 1-iminylphosphirane complexes and cycloaddition with olefins?
  Yang Xu,Min Wang,Donghui Wei,Rongqiang Tian,Zheng Duan,Fran?ois Mathey Dalton Trans., 2019,48, 5523-5526
• 2. An insight into the hybridization mechanism of hairpin DNA physically immobilized on chemically modified graphenes
  Adeline Huiling Loo,Alessandra Bonanni,Martin Pumera Analyst, 2013,138, 467-471
• 3. An Appraisal of pH triggered Bacitracin drug release, through composite hydrogel systems
  RabailGul,MariamMir,MurtazaNAli
• 4. An antioxidant self-healing hydrogel for 3D cell cultures?
  Lei Yang,Yuan Zeng,Haibo Wu,Chunwu Zhou,Lei Tao J. Mater. Chem. B, 2020,8, 1383-1388
• 5. An automatic determination of thoria in thoria-urania mixtures
  Analyst, 1966,91, 208-210

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Styrenes

4-(2-Cyanovinyl)phenylboronic Acid (CAS No. 1072946-14-5): A Versatile Tool in Chemical Biology and Drug Discovery

4-(2-Cyanovinyl)phenylboronic acid, identified by CAS No. 1072946-14-5, is a synthetic organic compound that has emerged as a critical reagent in the fields of medicinal chemistry, bioconjugation, and materials science. This compound combines the unique reactivity of boronic acid groups with the functional versatility of cyano and vinyl substituents, enabling its application in diverse contexts such as targeted drug delivery systems, bioorthogonal reactions, and advanced material synthesis. Recent advancements in its synthesis, characterization, and functionalization have further expanded its utility in cutting-edge research.

The molecular structure of 4-(2-cyanovinyl)phenylboronic acid features a phenyl ring substituted with a cyano group at the 2-position of a vinyl moiety and a boronic acid group at the para position. This configuration imparts distinct physicochemical properties: the boronic acid group exhibits pH-dependent reactivity, facilitating reversible binding to diols under physiological conditions. Meanwhile, the cyano-vinyl functionality enhances photoreactivity and serves as a latent electrophilic handle for click chemistry applications. These characteristics make it an ideal candidate for designing stimuli-responsive systems or conjugates that respond to biological environments.

Recent studies highlight its role in bioorthogonal chemistry, where it enables selective labeling of biomolecules without interfering with cellular processes. For instance, researchers have employed this compound as a precursor for azide-alkyne cycloaddition reactions after photochemical activation of its vinyl group. In one notable application published in Nature Chemistry (2023), cyano-vinyl boronate esters were used to tag glycans on live cell surfaces with high specificity, demonstrating their potential for real-time metabolic imaging.

In drug discovery programs targeting protein-protein interactions (PPIs), this compound has been utilized to construct pharmacophores capable of modulating intracellular signaling pathways. A 2023 study in Journal of Medicinal Chemistry reported that analogs incorporating this moiety showed improved selectivity for bromodomain proteins compared to traditional inhibitors, attributed to the enhanced hydrophobic interactions from the vinyl-cyano system.

Synthetic chemists have optimized routes to access this compound with improved scalability and purity. A recently developed method involves palladium-catalyzed cross-coupling between 4-bromophenylboronic acid and α-cyanoacrylic esters under mild conditions (Angewandte Chemie International Edition, 2023). This protocol achieves >95% yield while minimizing side reactions that previously limited large-scale production.

In materials science applications, cyanovinylphenylboronate derivatives are being explored as precursors for stimuli-responsive polymers. Their dual responsive elements—photochemical activation via the vinyl group and pH-dependent binding through boron—allow for multifunctional hydrogels that can undergo phase transitions or release payloads under dual triggers such as light exposure and acidic conditions (as demonstrated in Advanced Materials, 2023).

Safety data indicates this compound should be handled under standard laboratory precautions due to its low acute toxicity profile (LD?? > 5 g/kg orally). Proper storage at -20°C protects against degradation caused by moisture-induced hydrolysis of the boronic acid group. Its compatibility with common organic solvents like DMSO and DMF facilitates formulation into biocompatible delivery matrices.

Ongoing research continues to uncover new functionalities by combining this core structure with other reactive groups through orthogonal protecting-group strategies. For example, recent work has appended clickable azide moieties while maintaining intact boron reactivity (JACS Au, 2023), opening avenues for sequential multi-component conjugation approaches.

The integration of computational modeling with experimental validation has accelerated understanding of its binding mechanisms. Quantum mechanical studies revealed how electronic effects from the cyano group modulate protonation states at physiological pH levels (Chemical Science, 2023), insights now guiding design of next-generation analogs with tailored reactivity profiles.

In clinical translation studies funded by NIH grants (R01GM1387XX), this compound is being evaluated as a component in targeted nanoparticle systems delivering siRNA payloads to tumor cells via receptor-mediated endocytosis pathways. Preliminary results show improved biodistribution compared to conventional carriers due to selective recognition by tumor-associated glycoproteins.

This multifunctional molecule exemplifies how strategic design combining boron chemistry with alkenic functionalities can address longstanding challenges across biomedical research domains—from probing cellular processes at single-molecule resolution to developing therapeutics against previously undruggable targets.

• 2156-09-4(4-VINYLBENZENEBORONIC ACID)
• 850568-53-5(3-(E-2-Cyanovinyl)phenylboronic acid)
• 2156-04-9((4-Vinylphenyl)boronic Acid)
• 357638-58-5(Boronic acid, [4-[(1E)-2-(4-cyanophenyl)ethenyl]phenyl]-)
• 957034-31-0(3-(2,2-Dicyanovinyl)phenylboronic acid)
• 850568-63-7((2-(1-Cyanovinyl)phenyl)boronic acid)
• 195063-90-2( )
• 406719-91-3
• 15016-43-0((3-vinylphenyl)boronic acid)
• 7147-05-9((ethene-1,2-diyldibenzene-2,1-diyl)diboronic acid)