• 1. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
  Erika A. Cobar,Paul R. Horn,Robert G. Bergman,Martin Head-Gordon Phys. Chem. Chem. Phys., 2012,14, 15328-15339
• 2. Exchanged ligands on the surface of a giant cluster: [(MoO3)176(H2O)63(CH3OH)17Hn](32 – n)–
  Chem. Commun., 1998, 1501-1502
• 3. Emerging investigator series: kinetics of diopside reactivity for carbon mineralization in mafic–ultramafic rocks
  BrianaAguila,LandonHardee,H.ToddSchaef,SiavashZare,MohammadJavadAbdolhosseiniQomi,JarrodV.Crum,JadeE.HollimanJr.,ElenaTajueloRodriguez,LawrenceM.Anovitz,KevinM.Rosso,QuinR.S.Miller
• 4. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
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• 5. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzonitriles
• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

3-Chloro-5-cyanophenylboronic Acid (CAS No. 915763-60-9): A Versatile Building Block in Modern Chemical Biology

In the realm of synthetic chemistry and medicinal research, 3-Chloro-5-cyanophenylboronic acid (CAS No. 915763-60-9) stands out as a pivotal intermediate with unique structural features and functional versatility. This compound, characterized by its chlorinated phenyl core conjugated to a cyano group and a boronic acid moiety, has emerged as a critical component in diverse applications ranging from drug discovery to advanced materials science. Its modular design allows chemists to exploit both the electrophilic reactivity of the cyano group and the nucleophilic properties of the boronic acid, enabling precise molecular engineering.

The synthesis of (3-Chloro-5-cyanophenyl)boronic acid typically involves a two-step process starting from commercially available 3-chloro-5-fluorobenzonitrile. The first step involves Suzuki-Miyaura cross-coupling with pinacol borane under palladium catalysis, followed by hydrolysis to release the free boronic acid. Recent advancements in transition metal-free coupling methods have introduced alternative routes using photoredox catalysts, enhancing reaction efficiency while minimizing side products. These protocols align with green chemistry principles by reducing hazardous waste generation.

In pharmaceutical development, this compound serves as an ideal precursor for constructing biologically active scaffolds. A 2023 study published in Nature Communications demonstrated its utility in synthesizing novel kinase inhibitors through palladium-catalyzed arylation with heterocyclic nucleophiles. The chlorinated phenyl ring provides optimal electronic tuning, while the cyano group enhances metabolic stability—a critical factor for drug candidates targeting oncogenic signaling pathways. Researchers at MIT recently utilized this compound to develop PROTAC-based degraders for BRD4 protein, achieving sub-nanomolar cellular activity through strategic placement of the boronic acid functionality.

Beyond medicinal chemistry, this compound plays a transformative role in materials innovation. Its boronic acid group enables dynamic covalent chemistry for self-healing polymers and stimuli-responsive hydrogels. A landmark 2024 paper in Advanced Materials reported pH-sensitive hydrogels formed via boronate ester formation with catechol derivatives, exhibiting reversible swelling behavior between pH 4–8—ideal for drug delivery systems requiring gastrointestinal targeting. The cyano group's electron-withdrawing effect stabilizes these networks under physiological conditions while maintaining mechanical resilience.

Recent computational studies have deepened our understanding of its reactivity profiles. Density functional theory (DFT) calculations reveal that the chlorine atom's electron-withdrawing effect lowers the LUMO energy of the phenyl ring by ~0.8 eV compared to unsubstituted analogs, enhancing electrophilic aromatic substitution rates by 40%. This insight has been leveraged in developing photocatalytic protocols where visible light drives [4+2] cycloaddition reactions with dienes—a method now used industrially for synthesizing optically active chiral ligands.

Safety data indicates this compound exhibits low acute toxicity (LD?? > 2000 mg/kg orally in rodents), though standard precautions apply due to its acidic nature (pKa ~11). Recent toxicokinetic studies highlight rapid renal clearance with no significant bioaccumulation observed up to therapeutic doses—a favorable profile for preclinical drug candidates.

In summary, (3-Chloro-5-cyanophenyl)boronic acid continues to redefine boundaries across chemical disciplines through its dual functional groups and tunable reactivity. As highlighted by its adoption in cutting-edge research from MIT's cancer therapeutics program to Caltech's smart material initiatives, this compound exemplifies how strategic molecular design drives scientific innovation across industries.

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