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CS-W001157 4
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Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

  • CAS No. 195062-62-5

  • Cat. No. CS-0028748
  • Purity≥98%
  • MDL No.MFCD03453659

*For research and further manufacturing use only, not for direct human use.

Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate|CS-0028748

Structure of 195062-62-5

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General Information

  • CAS No. 195062-62-5
  • Cat. No. CS-0028748
  • Purity ≥98%
  • MDL No. MFCD03453659
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₁BO₄
  • Molecular Weight 276.14
  • Synonym(s) 4-Ethoxycarbonylphenylboronic Acid Pinacol Ester
  • SMILES O=C(OCC)C1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1

Description

Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate features a boronate ester group flanked by electron-rich tetramethylcyclopentadienone rings, enabling stable coupling in Suzuki-Miyaura reactions. The ethyl ester handle allows for selective derivatization, while the sterically shielded boron center resists protodeboronation and hydrolysis under standard conditions. This bench-stable reagent integrates seamlessly into modular synthesis workflows.

Application

Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate serves as a robust boronate ester building block for Suzuki-Miyaura cross-coupling reactions. Its stability under ambient conditions and tolerance to a wide range of functional groups enable reliable C–C bond formation in complex molecule synthesis. The dioxaborolane moiety facilitates efficient palladium-catalyzed coupling with aryl halides and pseudohalides, making it ideal for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Mo, Fanyang; Jiang, Yubo; Qiu, Di; Zhang, Yan; Wang, Jianbo Angewandte Chemie - International Edition, 2010 , vol. 49, # 10 p. 1846 - 1849
  • Route2
    • In-stock
      Methyl 4-iodobenzoate|CS-W007583
      619-44-3
    • null|null
      25015-63-8
    • ~%
    • In-stock
      Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate|CS-0028748
      195062-62-5

    References

    • US2003/195352 A1, ; Page/Page column 34 ;
  • Route3

    References

    • Claudel, Stephanie; Gosmini, Corinne; Paris, Jean Marc; Perichon, Jacques Chemical Communications, 2007 , # 35 p. 3667 - 3669

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   44.76
  • LogP   2.1625
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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