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1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine

  • CAS No. 912369-50-7

  • Cat. No. CS-0175631
  • Purity≥96%
  • MDL No.MFCD06795649

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

1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine|CS-0175631

Structure of 912369-50-7

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General Information

  • CAS No. 912369-50-7
  • Cat. No. CS-0175631
  • Purity ≥96%
  • MDL No. MFCD06795649
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₂₅BN₂O₂
  • Molecular Weight 288.20
  • Synonym(s) None
  • SMILES O1B(OC(C)(C)C1(C)C)C2=CC=C(C=C2)N3CCNCC3

Description

1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine features a boronate ester handle enabling robust Suzuki-Miyaura coupling under mild conditions. The piperazine moiety provides solubility and polarity, while the tetramethyl-substituted dioxaborolane enhances stability and shelf life. This compound integrates efficiently into complex molecular architectures during medicinal chemistry campaigns.

Application

1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. Its piperazine moiety offers enhanced solubility and metabolic stability, while the tetramethylboronate group enables robust coupling under mild conditions. The compound exhibits excellent bench stability, facilitates straightforward purification, and functions reliably in the synthesis of biologically relevant heterocyclic scaffolds and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • WO2006/106326 A1, ; Page/Page column 133 ; WO 2006/106326 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 : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   33.73
  • LogP   1.3954
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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