Cas no 1220219-11-3 (3-Cyano-4-methylphenylboronic acid, pinacol ester)

3-Cyano-4-methylphenylboronic acid pinacol ester is a boronic acid derivative commonly employed in Suzuki-Miyaura cross-coupling reactions due to its stability and reactivity. The pinacol ester group enhances shelf life and handling by protecting the boronic acid moiety from protodeboronation and oxidation. The cyano and methyl substituents on the phenyl ring influence electronic and steric properties, making it a versatile intermediate in pharmaceutical and materials science applications. Its crystalline solid form ensures consistent purity and ease of quantification in synthetic procedures. This compound is particularly useful in constructing complex aromatic systems where controlled functionalization is required.
3-Cyano-4-methylphenylboronic acid, pinacol ester structure
1220219-11-3 structure
Product Name:3-Cyano-4-methylphenylboronic acid, pinacol ester
CAS No:1220219-11-3
MF:C14H18BNO2
MW:243.109223842621
MDL:MFCD18087706
CID:1084621
PubChem ID:53216769
Update Time:2025-06-14

3-Cyano-4-methylphenylboronic acid, pinacol ester Chemical and Physical Properties

Names and Identifiers

    • 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
    • 3-Cyano-4-methylphenylboronic acid, pinacol ester
    • B-2347
    • 2-METHYL-5-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
    • Z2044788601
    • MFCD18087706
    • 1220219-11-3
    • DB-366390
    • SY211508
    • 3-Cyano-4-methylphenylboronic acid pinacol ester
    • AKOS022176094
    • DTXSID20681916
    • BS-21241
    • 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, AldrichCPR
    • AT16358
    • SCHEMBL13089217
    • 3-Cyano-4-methylphenylboronic acid,pinacol ester
    • Benzonitrile, 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
    • CS-0134575
    • EN300-317550
    • MDL: MFCD18087706
    • Inchi: 1S/C14H18BNO2/c1-10-6-7-12(8-11(10)9-16)15-17-13(2,3)14(4,5)18-15/h6-8H,1-5H3
    • InChI Key: WXENCUOINPORPY-UHFFFAOYSA-N
    • SMILES: O1B(C2C=CC(C)=C(C#N)C=2)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 243.14300
  • Monoisotopic Mass: 243.1430590g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 1
  • Complexity: 355
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 42.2?2

Experimental Properties

  • PSA: 42.25000
  • LogP: 2.16588

3-Cyano-4-methylphenylboronic acid, pinacol ester Customs Data

  • HS CODE:2934999090
  • Customs Data:

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

3-Cyano-4-methylphenylboronic acid, pinacol ester Pricemore >>

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Additional information on 3-Cyano-4-methylphenylboronic acid, pinacol ester

Recent Advances in the Application of 3-Cyano-4-methylphenylboronic acid, pinacol ester (CAS: 1220219-11-3) in Chemical Biology and Pharmaceutical Research

3-Cyano-4-methylphenylboronic acid, pinacol ester (CAS: 1220219-11-3) is a boronic acid derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound, characterized by its cyano and methyl substituents on the phenyl ring and the pinacol ester protecting group, serves as a crucial building block in Suzuki-Miyaura cross-coupling reactions, which are widely employed in the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals. The unique electronic and steric properties of this boronic ester make it particularly valuable for the construction of biaryl systems, which are prevalent in many bioactive compounds.

Recent studies have highlighted the role of 3-Cyano-4-methylphenylboronic acid, pinacol ester in the development of novel therapeutic agents. For instance, researchers have utilized this compound as a key intermediate in the synthesis of tyrosine kinase inhibitors, which are pivotal in targeted cancer therapies. The boronic ester moiety facilitates the formation of carbon-carbon bonds under mild conditions, enabling the efficient assembly of structurally diverse inhibitors with enhanced selectivity and potency. Additionally, its stability under physiological conditions has made it a promising candidate for prodrug strategies, where the boronic acid is released upon enzymatic cleavage in vivo.

In the context of chemical biology, 3-Cyano-4-methylphenylboronic acid, pinacol ester has been employed as a molecular probe to investigate protein-ligand interactions. Its ability to form reversible covalent bonds with diols and other nucleophiles has been exploited in the design of activity-based probes for glycosidases and other enzymes. Recent work has demonstrated its utility in profiling enzyme activities in complex biological samples, providing insights into disease mechanisms and potential therapeutic targets. Furthermore, the compound's fluorescence properties have been leveraged for the development of biosensors, enabling real-time monitoring of enzymatic reactions and cellular processes.

Despite its promising applications, challenges remain in the optimization of 3-Cyano-4-methylphenylboronic acid, pinacol ester for specific biomedical uses. Issues such as solubility, bioavailability, and off-target effects need to be addressed through structural modifications and formulation strategies. Recent advances in computational chemistry and high-throughput screening have facilitated the rational design of derivatives with improved pharmacokinetic profiles. Collaborative efforts between chemists, biologists, and pharmacologists are essential to fully harness the potential of this compound in drug discovery and development.

Looking ahead, the integration of 3-Cyano-4-methylphenylboronic acid, pinacol ester into emerging technologies such as PROTACs (Proteolysis Targeting Chimeras) and antibody-drug conjugates (ADCs) holds great promise. Its compatibility with bioorthogonal chemistry and click reactions further expands its utility in bioconjugation and targeted delivery systems. As research continues to uncover new applications and refine existing methodologies, this boronic ester is poised to play an increasingly important role in the advancement of chemical biology and pharmaceutical sciences.

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