Cas no 1256355-31-3 ((3-(Benzyloxy)-4-methylphenyl)boronic acid)

(3-(Benzyloxy)-4-methylphenyl)boronic acid is a boronic acid derivative featuring a benzyl-protected hydroxyl group and a methyl substituent on the phenyl ring. This compound is widely utilized in Suzuki-Miyaura cross-coupling reactions due to its stability and reactivity with various aryl halides, enabling the synthesis of complex biaryl structures. The benzyloxy group enhances solubility in organic solvents, facilitating handling in synthetic applications. Its well-defined structure and consistent purity make it a reliable reagent for pharmaceutical and materials science research. The compound is particularly valuable in constructing intermediates for drug discovery and functional materials, where precise control over molecular architecture is critical. Proper storage under inert conditions ensures long-term stability.
(3-(Benzyloxy)-4-methylphenyl)boronic acid structure
1256355-31-3 structure
Product Name:(3-(Benzyloxy)-4-methylphenyl)boronic acid
CAS No:1256355-31-3
MF:C14H15BO3
MW:242.078104257584
MDL:MFCD11617255
CID:828707
Update Time:2025-10-31

(3-(Benzyloxy)-4-methylphenyl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • (3-(Benzyloxy)-4-methylphenyl)boronic acid
    • (4-methyl-3-phenylmethoxyphenyl)boronic acid
    • 3-(Benzyloxy)-4-Methylphenylboronic acid
    • MDL： MFCD11617255
    • Inchi： 1S/C14H15BO3/c1-11-7-8-13(15(16)17)9-14(11)18-10-12-5-3-2-4-6-12/h2-9,16-17H,10H2,1H3
    • InChI Key： NJDWFMZIGIGFTM-UHFFFAOYSA-N
    • SMILES： O(CC1C=CC=CC=1)C1C=C(B(O)O)C=CC=1C

Computed Properties

  • Exact Mass: 242.11100
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 4

Experimental Properties

  • Density: 1.17±0.1 g/cm3 (20 oC 760 Torr),
  • Solubility: Very slightly soluble (0.11 g/l) (25 o C),
  • PSA: 49.69000
  • LogP: 1.25380

(3-(Benzyloxy)-4-methylphenyl)boronic acid Customs Data

  • HS CODE：2931900090
  • Customs Data：

    China Customs Code:

    2931900090

    Overview:

    2931900090. Other organic-Inorganic compound. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:AB(Customs clearance form for Inbound Goods,Customs clearance form for outbound goods). MFN tariff:6.5%. general tariff:30.0%

    Summary:

    2931900090. other organo-inorganic compounds. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward). MFN tariff:6.5%. General tariff:30.0%

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(3-(Benzyloxy)-4-methylphenyl)boronic acid Related Literature

Related Categories

Additional information on (3-(Benzyloxy)-4-methylphenyl)boronic acid

Recent Advances in the Application of (3-(Benzyloxy)-4-methylphenyl)boronic acid (CAS: 1256355-31-3) in Chemical Biology and Pharmaceutical Research

Boronic acids have emerged as pivotal compounds in chemical biology and pharmaceutical research due to their unique reactivity and versatility in organic synthesis, drug design, and sensing applications. Among these, (3-(Benzyloxy)-4-methylphenyl)boronic acid (CAS: 1256355-31-3) has garnered significant attention for its potential in targeted drug delivery, enzyme inhibition, and as a building block in the synthesis of complex bioactive molecules. This research brief synthesizes the latest findings on this compound, highlighting its applications, mechanisms, and future directions in the field.

Recent studies have demonstrated the utility of (3-(Benzyloxy)-4-methylphenyl)boronic acid in Suzuki-Miyaura cross-coupling reactions, a cornerstone methodology in the construction of biaryl structures prevalent in pharmaceuticals. Its benzyloxy and methyl substituents enhance steric and electronic properties, improving yield and selectivity in these reactions. For instance, a 2023 study published in the Journal of Medicinal Chemistry utilized this boronic acid derivative to synthesize novel kinase inhibitors, showcasing its role in developing targeted cancer therapies.

Beyond synthetic applications, (3-(Benzyloxy)-4-methylphenyl)boronic acid has shown promise in glucose sensing and glycoprotein recognition. Its ability to form reversible covalent bonds with diols makes it a candidate for non-invasive glucose monitoring systems. A recent Nature Biomedical Engineering paper highlighted its integration into a hydrogel-based sensor, achieving high sensitivity and specificity for continuous glucose monitoring in diabetic patients. This innovation underscores the compound's potential in medical diagnostics.

In drug discovery, the compound's boronic acid moiety facilitates proteasome inhibition, a mechanism exploited in therapies for multiple myeloma. Research published in Blood Cancer Journal (2024) revealed its derivative's efficacy in overcoming bortezomib resistance, attributed to enhanced binding affinity to the proteasome's β5 subunit. Structural modifications, including the benzyloxy group, were critical in optimizing pharmacokinetic properties while minimizing off-target effects.

Challenges remain in the compound's solubility and bioavailability, prompting investigations into prodrug strategies and nanoformulations. A 2024 ACS Nano study demonstrated that encapsulating (3-(Benzyloxy)-4-methylphenyl)boronic acid in polymeric nanoparticles improved its tumor accumulation by 3-fold in murine models, addressing delivery hurdles. Such advancements pave the way for clinical translation.

In conclusion, (3-(Benzyloxy)-4-methylphenyl)boronic acid (CAS: 1256355-31-3) exemplifies the convergence of chemical innovation and therapeutic potential. Its multifaceted applications—from synthetic chemistry to precision medicine—highlight its value as a research tool and therapeutic agent. Future work should focus on optimizing its physicochemical properties and expanding its utility in emerging areas like theranostics and covalent drug design.

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