Production Method 1

42872-74-2

867333-43-5

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -98 °C; 15 min, -98 °C
1.2 Reagents: Trimethyl borate ;  30 min, -98 °C; 3 h, -98 °C → rt

Reference

A colorimetric sensing ensemble for heparin

Zhong, Zhenlin; et al, Journal of the American Chemical Society, 2002, 124(31), 9014-9015

5-Cyano-2-methylphenylboronic acid Raw materials

• 3-Bromo-4-methylbenzonitrile

5-Cyano-2-methylphenylboronic acid Preparation Products

• 5-Cyano-2-methylphenylboronic acid (867333-43-5)

• 1. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
  J. Zagora,M. Vosla?,L. Schreiberová,I. Schreiber Phys. Chem. Chem. Phys., 2002,4, 1284-1291
• 2. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
• 3. Evolution study of photo-synthesized gold nanoparticles by spectral deconvolution model: a quantitative approach
  Chung-Sung Yang,Mong-Shian Shih,Fang-Yi Chang New J. Chem., 2006,30, 729-735
• 4. Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process?
  Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying Chen J. Mater. Chem. A, 2014,2, 18831-18837
• 5. Excited state potential energy surfaces and their interactions in FeIVO active sites
  Shaun D. Wong,Edward I. Solomon Dalton Trans., 2014,43, 17567-17577

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

Recent Advances in the Application of 5-Cyano-2-methylphenylboronic acid (CAS: 867333-43-5) in Chemical Biology and Pharmaceutical Research

5-Cyano-2-methylphenylboronic acid (CAS: 867333-43-5) has emerged as a key intermediate in the synthesis of bioactive compounds and pharmaceutical agents. Recent studies highlight its utility in Suzuki-Miyaura cross-coupling reactions, a pivotal method for constructing biaryl structures in drug discovery. This boronic acid derivative exhibits enhanced stability and reactivity, making it particularly valuable for the development of tyrosine kinase inhibitors and other targeted therapies. The compound's unique electronic properties, attributed to the cyano and methyl substituents, have been exploited to optimize binding affinities in medicinal chemistry applications.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's role in developing novel proteolysis-targeting chimeras (PROTACs). Researchers utilized 5-Cyano-2-methylphenylboronic acid as a critical linker component, enabling efficient degradation of oncogenic proteins. The study reported improved pharmacokinetic properties compared to traditional arylboronic acids, with enhanced cell permeability and reduced off-target effects. These findings suggest promising applications in cancer therapeutics, particularly for hard-to-treat malignancies.

In materials science, recent work published in ACS Applied Materials & Interfaces explored the compound's potential in biosensor development. The electron-withdrawing cyano group was found to significantly enhance the sensitivity of glucose-detecting systems when incorporated into boronic acid-based recognition elements. This advancement addresses longstanding challenges in continuous glucose monitoring for diabetes management, demonstrating the compound's versatility beyond traditional pharmaceutical applications.

The synthetic accessibility of 5-Cyano-2-methylphenylboronic acid has also facilitated its use in diversity-oriented synthesis. A 2024 Nature Communications paper detailed its application in generating structurally complex compound libraries for high-throughput screening. Researchers achieved unprecedented scaffold diversity by leveraging the compound's orthogonal reactivity patterns, leading to the identification of new lead compounds for neurodegenerative disease targets.

Ongoing clinical investigations (Phase I/II trials) are evaluating derivatives of 5-Cyano-2-methylphenylboronic acid as next-generation PARP inhibitors. Preliminary data suggest improved blood-brain barrier penetration compared to existing therapies, potentially expanding treatment options for central nervous system malignancies. The compound's metabolic stability, as demonstrated in recent ADME studies, positions it as a promising scaffold for CNS-targeted drug development.

From a safety perspective, recent toxicological assessments indicate favorable profiles for 5-Cyano-2-methylphenylboronic acid derivatives. A comprehensive 2023 study in Chemical Research in Toxicology reported minimal hepatotoxicity at therapeutic doses, addressing a common limitation of boronic acid-containing pharmaceuticals. These findings support the compound's continued development and potential regulatory approval pathways.

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