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CS-W001157 4
Total: USD 88.00

1-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

  • CAS No. 1151802-22-0

  • Cat. No. CS-W000818
  • Purity≥97%
  • MDL No.MFCD16659007

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

1-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole|CS-W000818

Structure of 1151802-22-0

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General Information

  • CAS No. 1151802-22-0
  • Cat. No. CS-W000818
  • Purity ≥97%
  • MDL No. MFCD16659007
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₉BN₂O₂
  • Molecular Weight 234.10
  • Synonym(s) 1-cyclopropylpyrazole-4-boronic acid pinacol ester
  • SMILES CC1(C)OB(OC1(C)C)c1cnn(c1)C1CC1

Description

1-Cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole features a boronate ester group that enables efficient Suzuki-Miyaura cross-coupling reactions. The cyclopropyl substituent imparts structural rigidity and favorable lipophilicity, enhancing metabolic stability in bioactive molecule synthesis. This bench-stable reagent integrates seamlessly into complex molecular architectures under standard conditions.

Application

1-Cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. The cyclopropylpyrazole core provides metabolic stability and favorable physicochemical properties, while the pinacol boronate moiety enables efficient coupling under mild conditions. Bench-stable and compatible with diverse functional groups, it facilitates rapid access to substituted pyrazole scaffolds in medicinal chemistry and materials synthesis.

Synthesis

  • Route1
    • null|null
      61676-62-8
    • In-stock
      1-Cyclopropyl-4-iodo-1H-pyrazole|CS-0037329
      1239363-40-6
    • ~83%
    • In-stock
      1-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole|CS-W000818
      1151802-22-0

    References

    • Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael Patent: US2011/230462 A1, 2011 ; Location in patent: Page/Page column 84 ; US 20110230462 A1
  • Route2

    References

    • WO2010/141273 A1, ; Page/Page column 53 ;
  • Route3
    • null|null
      61676-62-8
    • In-stock
      4-Bromo-1-cyclopropyl-1H-pyrazole|CS-W000378
      1151802-23-1
    • ~%
    • In-stock
      1-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole|CS-W000818
      1151802-22-0

    References

    • WO2014/32498 A1, ; Page/Page column 18-19 ;

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   36.28
  • LogP   1.5172
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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