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tert-Butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate

  • CAS No. 496786-98-2

  • Cat. No. CS-M2404
  • Purity≥95%
  • MDL No.MFCD04039875

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

tert-Butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate|CS-M2404

Structure of 496786-98-2

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General Information

  • CAS No. 496786-98-2
  • Cat. No. CS-M2404
  • Purity ≥95%
  • MDL No. MFCD04039875
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₃₂BN₃O₄
  • Molecular Weight 389.30
  • Synonym(s) 2-[4-(N-Boc)piperazin-1-yl]pyridine-5-boronic acid pinacol ester
  • SMILES CC1(C)C(C)(C)OB(C2=CN=C(N3CCN(C(OC(C)(C)C)=O)CC3)C=C2)O1

Description

tert-Butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate features a boronate ester group enabling robust Suzuki-Miyaura coupling. The piperazine scaffold provides a versatile nitrogen-rich platform for diversification. Bench-stable and moisture-tolerant, this reagent streamlines access to complex pyridyl-piperazine architectures in medicinal chemistry and materials science.

Application

tert-Butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The piperazine moiety provides a polar, basic nitrogen scaffold useful in medicinal chemistry, while the tert-butyl carbamate offers stability and ease of removal under mild acidic conditions. Functional group tolerance enables reliable coupling with diverse aryl and heteroaryl halides, facilitating rapid access to complex molecular architectures in drug discovery workflows.

Synthesis

  • Route1

    References

    • Journal of Medicinal Chemistry, , vol. 55, # 11 p. 5361 - 5379

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   64.13
  • LogP   2.4379
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   2

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