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N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

  • CAS No. 400727-57-3

  • Cat. No. CS-0094696
  • Purity≥97%
  • MDL No.MFCD05863908

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

N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide|CS-0094696

Structure of 400727-57-3

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General Information

  • CAS No. 400727-57-3
  • Cat. No. CS-0094696
  • Purity ≥97%
  • MDL No. MFCD05863908
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₂BNO₃
  • Molecular Weight 275.15
  • Synonym(s) N-DiMethyl-3-(4
  • SMILES O=C(N(C)C)C1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1

Description

N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide delivers a boronate handle with enhanced stability and solubility, enabling efficient Suzuki-Miyaura coupling under mild conditions. The dimethylamino group imparts electron-rich character, promoting reactivity in cross-coupling processes while maintaining bench-stable handling properties.

Application

N,N-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The dimethylamino group enhances solubility and electronic modulation, while the tetramethylboronate moiety ensures high reactivity and functional group tolerance under standard coupling conditions. This compound facilitates efficient construction of biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • US2014/140956 A1, ; Paragraph 0677; 0679 ;
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 122, # 51 p. 12868 - 12869
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    References

    • US2014/140956 A1, ;

Safety Information

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

Quality Control

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Computational Chemistry Data

  • TPSA   38.77
  • LogP   1.6876
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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