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CS-W001157 4
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3,5-Diisopropyl-1H-pyrazole

  • CAS No. 17536-00-4

  • Cat. No. CS-0203556
  • Molecule weightNone
  • Purity≥95%
  • MDL No.MFCD00671516

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

3,5-Diisopropyl-1H-pyrazole|CS-0203556

Structure of 17536-00-4

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General Information

  • CAS No. 17536-00-4
  • Cat. No. CS-0203556
  • Purity ≥95%
  • MDL No. MFCD00671516
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₆N₂
  • Molecular Weight None
  • Synonym(s) 3,5-Diisopropylpyrazole
  • SMILES CC(C1=CC(C(C)C)=NN1)C

Description

3,5-Diisopropyl-1H-pyrazole features a sterically hindered pyrazole core with two bulky isopropyl groups at the 3 and 5 positions, enhancing stability and solubility in organic media. This configuration imparts resistance to decomposition under standard bench conditions, enabling reliable use in synthetic transformations requiring robust heterocyclic scaffolds.

Application

3,5-Diisopropyl-1H-pyrazole serves as a sterically hindered pyrazole scaffold with enhanced solubility and bench stability, enabling its use in medicinal chemistry lead optimization. The diisopropyl substitution pattern provides favorable steric shielding of the nitrogen atoms, improving metabolic resistance and reducing unwanted side reactions during downstream functionalization. It functions effectively as a bioisostere for phenyl or other heterocycles in API development and facilitates efficient coupling reactions due to its moderate nucleophilicity and compatibility with standard synthetic protocols.

Synthesis

  • Route1

    References

    • Kitajima, Nobumasa; Fujisawa, Kiyoshi; Fujimoto, Chisato; Moro-oka, Yoshihiko; Hashimoto, Shinji; Kitagawa, Teizo; Toriumi, Koshiro; Tatsumi, Kazuyuki; Nakamura, Akira Journal of the American Chemical Society, 1992 , vol. 114, # 4 p. 1277 - 1291
  • Route2
    • null|null
      671246-69-8
    • ~80%
    • In-stock
      3,5-Diisopropyl-1H-pyrazole|CS-0203556
      17536-00-4

    References

    • Dastrup, David M.; Yap, Amy H.; Weinreb, Steven M.; Henry, James R.; Lechleiter, Andrew J. Tetrahedron, 2004 , vol. 60, # 4 p. 901 - 906
  • Route3
    • null|null
      563-80-4
    • ~%
    • In-stock
      3,5-Diisopropyl-1H-pyrazole|CS-0203556
      17536-00-4

    References

    • Journal of the American Chemical Society, , vol. 114, # 4 p. 1277 - 1291

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

Quality Control

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Computational Chemistry Data

  • TPSA   28.68
  • LogP   2.6565
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   2

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