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CS-W001157 4
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3-[4-(N-Boc)piperazin-1-yl]phenylboronic acid pinacol ester

  • CAS No. 540752-87-2

  • Cat. No. CS-0060945
  • Purity≥97%
  • MDL No.None

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

3-[4-(N-Boc)piperazin-1-yl]phenylboronic acid pinacol ester|CS-0060945

Structure of 540752-87-2

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General Information

  • CAS No. 540752-87-2
  • Cat. No. CS-0060945
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₁H₃₃BN₂O₄
  • Molecular Weight 388.31
  • Synonym(s) Tert-butyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)piperazine-1-carboxylate
  • SMILES CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=CC(=C2)B3OC(C)(C)C(C)(C)O3

Description

This boronate ester integrates a Boc-protected piperazine moiety with a phenylboronic acid pinacol ester, enabling stable, orthogonal functionalization in cross-coupling reactions. The electron-rich aryl group enhances reactivity under standard conditions, while the pinacol protection ensures bench-stable handling and improved solubility in polar organic solvents.

Application

3-[4-(N-Boc)piperazin-1-yl]phenylboronic acid pinacol ester serves as a stable, bench-ready building block for Suzuki-Miyaura cross-coupling reactions. The pinacol boronate ester enhances shelf life and handling safety, while the N-Boc-protected piperazine moiety enables subsequent deprotection and diversification. It exhibits excellent functional group tolerance and facilitates the construction of complex biaryl scaffolds relevant to medicinal chemistry and materials science.

Synthesis

  • Route1
    • null|null
      540752-86-1
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~81%
    • In-stock
      3-[4-(N-Boc)piperazin-1-yl]phenylboronic acid pinacol ester|CS-0060945
      540752-87-2

    References

    • Matasi, Julius J.; Caldwell, John P.; Zhang, Hongtao; Fawzi, Ahmad; Higgins, Guy A.; Cohen-Williams, Mary E.; Varty, Geoffrey B.; Tulshian, Deen B. Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 16 p. 3675 - 3678
  • Route2

    References

    • Castillo, Marcos; Forns, Pilar; Erra, Montse; Mir, Marta; Lopez, Manel; Maldonado, Monica; Orellana, Adelina; Carreno, Cristina; Ramis, Isabel; Miralpeix, Montserrat; Vidal, Bernat Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 17 p. 5419 - 5423
  • Route3
    • N-Boc-piperazine Olaparib Impurity|CS-0214004
      57260-71-6
    • ~%
    • In-stock
      3-[4-(N-Boc)piperazin-1-yl]phenylboronic acid pinacol ester|CS-0060945
      540752-87-2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 15, # 16 p. 3675 - 3678

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

Quality Control

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Computational Chemistry Data

  • TPSA   51.24
  • LogP   3.0429
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   2

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