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CS-W001157 4
Total: USD 88.00

6-Bromopyrazolo[1,5-a]pyrimidine

  • CAS No. 705263-10-1

  • Cat. No. CS-M2471
  • Purity≥97%
  • MDL No.MFCD09832894

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

6-Bromopyrazolo[1,5-a]pyrimidine|CS-M2471

Structure of 705263-10-1

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General Information

  • CAS No. 705263-10-1
  • Cat. No. CS-M2471
  • Purity ≥97%
  • MDL No. MFCD09832894
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄BrN₃
  • Molecular Weight 198.02
  • Synonym(s) 6-BROMO-PYRAZOLO[1,5-A]PYRIMIDINE
  • SMILES BrC1=CN2C(N=C1)=CC=N2

Description

6-Bromopyrazolo[1,5-a]pyrimidine serves as a pivotal heterocyclic scaffold for constructing bioactive molecules. This brominated pyrazolopyrimidine features a reactive site at the 6-position, enabling facile cross-coupling reactions. The electron-deficient core supports efficient functionalization in medicinal chemistry and materials science applications.

Application

6-Bromopyrazolo[1,5-a]pyrimidine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions to install diverse aryl and heteroaryl substituents. Its bromine at the C6 position exhibits high reactivity in Suzuki, Stille, and Negishi couplings, with excellent functional group tolerance and bench stability. The pyrazolo[1,5-a]pyrimidine core provides a rigid, electron-deficient scaffold suitable for kinase inhibitor development and other bioactive molecule synthesis.

Synthesis

  • Route1
    • In-stock
      3-Aminopyrazole|CS-D1141
      1820-80-0
    • null|null
      2065-75-0
    • ~59%
    • In-stock
      6-Bromopyrazolo[1,5-a]pyrimidine|CS-M2471
      705263-10-1

    References

    • THE GENERAL HOSPITAL CORPORATION; THE BRIGHAM AND WOMEN'S HOSPITAL, INC. Patent: WO2009/114180 A1, 2009 ; Location in patent: Page/Page column 71 ;
  • Route2

    References

    • WO2006/128692 A2, ; Page/Page column 86 ;
  • Route3
    • In-stock
      3-Aminopyrazole|CS-D1141
      1820-80-0
    • null|null
      20591-60-0
    • ~%
    • In-stock
      6-Bromopyrazolo[1,5-a]pyrimidine|CS-M2471
      705263-10-1

    References

    • WO2009/14620 A1, ; Page/Page column 36; 24 ; WO 2009/014620 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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   30.19
  • LogP   1.4918
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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