Cas no 1198615-87-0 (Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate)

Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate is a boronic ester derivative widely used as an intermediate in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions. The 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacol boronate) moiety enhances stability and handling under ambient conditions, while the ethyl ester group offers versatility for further functionalization. This compound is valued for its compatibility with a broad range of substrates and its role in constructing complex aromatic systems. Its crystalline solid form ensures ease of purification and storage. The product is commonly employed in pharmaceutical and materials science research for the efficient synthesis of biaryl and heteroaryl structures.
Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate structure
1198615-87-0 structure
Product Name:Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
CAS No:1198615-87-0
MF:C16H23BO4
MW:290.162425279617
MDL:MFCD18383986
CID:1029838
Update Time:2025-05-19

Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Chemical and Physical Properties

Names and Identifiers

    • Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
    • Ethyl 4-(4-chloro-3-methylphenyl)-4-oxobutanoate
    • AK134662
    • Benzoic acid, 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, ethyl ester
    • 3441AA
    • AM85087
    • SY103426
    • OR350167
    • ST2412946
    • AX8256430
    • 2-Methyl-3-ethoxycarbonyl-benzylboronic acid pinacol ester
    • 3-(Ethoxycarbonyl)-2-methylphenylboronic Acid Pinacol Ester
    • Ethyl 2-methyl-3-
    • MDL: MFCD18383986
    • Inchi: 1S/C16H23BO4/c1-7-19-14(18)12-9-8-10-13(11(12)2)17-20-15(3,4)16(5,6)21-17/h8-10H,7H2,1-6H3
    • InChI Key: JZZPYKYHYBXWEP-UHFFFAOYSA-N
    • SMILES: O1B(C2C=CC=C(C(=O)OCC)C=2C)OC(C)(C)C1(C)C

Computed Properties

  • Exact Mass: 290.16900
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 4
  • Complexity: 378
  • Topological Polar Surface Area: 44.8

Experimental Properties

  • PSA: 44.76000
  • LogP: 2.47090

Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 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%

Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Pricemore >>

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Additional information on Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Research Brief on Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS: 1198615-87-0) in Chemical Biology and Pharmaceutical Applications

Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS: 1198615-87-0) is a boronic ester derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a key intermediate in the synthesis of bioactive molecules, particularly in the development of boron-containing drugs, which are increasingly recognized for their therapeutic potential. The unique properties of the boronate moiety, including its ability to form reversible covalent bonds with diols and its role in Suzuki-Miyaura cross-coupling reactions, make this compound a valuable tool in medicinal chemistry and drug discovery.

Recent studies have highlighted the role of Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate in the synthesis of proteasome inhibitors and other targeted therapies. For instance, researchers have utilized this compound to develop novel boron-based inhibitors that selectively target cancer cell pathways. The boronic acid functional group, when incorporated into drug candidates, can enhance binding affinity and specificity, leading to improved therapeutic outcomes. Additionally, its stability under physiological conditions makes it an attractive candidate for further pharmaceutical development.

In the context of chemical biology, this compound has been employed as a building block for the design of molecular probes and sensors. Its ability to interact with biological macromolecules, such as proteins and nucleic acids, has enabled researchers to study complex cellular processes with high precision. Recent advancements in biorthogonal chemistry have further expanded its utility, allowing for the selective labeling and tracking of biomolecules in live cells. These applications underscore the compound's potential in both basic research and translational medicine.

From a synthetic perspective, Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate is often synthesized via palladium-catalyzed borylation reactions, which offer high yields and excellent regioselectivity. Recent methodological improvements have focused on optimizing reaction conditions to reduce byproduct formation and enhance scalability. These advancements are critical for the large-scale production of boron-containing pharmaceuticals, where purity and efficiency are paramount.

Looking ahead, the continued exploration of Ethyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate and related boronic esters is expected to yield new insights into their therapeutic mechanisms and applications. Ongoing research is investigating their potential in treating neurodegenerative diseases, infectious diseases, and inflammatory disorders. Furthermore, the integration of computational modeling and high-throughput screening techniques is accelerating the discovery of novel boron-based drug candidates, positioning this compound as a cornerstone of future pharmaceutical innovation.

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