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CS-W001157 4
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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

  • CAS No. 179117-44-3

  • Cat. No. CS-0097867
  • Molecule weight247.10
  • Purity≥97%
  • MDL No.MFCD05663887

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

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide|CS-0097867

Structure of 179117-44-3

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General Information

  • CAS No. 179117-44-3
  • Cat. No. CS-0097867
  • Purity ≥97%
  • MDL No. MFCD05663887
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₈BNO₃
  • Molecular Weight 247.10
  • Synonym(s) 4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER
  • SMILES O=C(C1=CC=C(C=C1)B2OC(C)(C(C)(O2)C)C)N

Description

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide features a boronate ester group that enables reliable Suzuki-Miyaura cross-coupling reactions under mild conditions. The tetramethyl-substituted dioxaborolane moiety enhances stability and shelf life, while the para-amide functionality provides a polar handle for downstream derivatization. This bench-stable reagent integrates seamlessly into synthetic workflows requiring aryl-boron coupling.

Application

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. Its stability, ease of handling, and tolerance to diverse functional groups make it ideal for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu Patent: US2012/252777 A1, 2012 ; Location in patent: Page/Page column 96 ; US 20120252777 A1
  • Route2
    • In-stock
      4-Iodobenzamide|CS-W016701
      3956-07-8
    • null|null
      25015-63-8
    • ~%
    • In-stock
      4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide|CS-0097867
      179117-44-3

    References

    • US6680401 B1, ; Page column 19-20 ;
  • Route3

    References

    • Yamamoto, Tetsuya; Morita, Tomoyuki; Takagi, Jun; Yamakawa, Tetsu Organic Letters, 2011 , vol. 13, # 21 p. 5766 - 5769

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   61.55
  • LogP   1.0847
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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