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CS-W001157 4
Total: USD 88.00

tert-Butyl 4-iodo-1H-pyrazole-1-carboxylate

  • CAS No. 121669-70-3

  • Cat. No. CS-W005556
  • Purity≥95%
  • MDL No.MFCD05663855

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

tert-Butyl 4-iodo-1H-pyrazole-1-carboxylate|CS-W005556

Structure of 121669-70-3

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General Information

  • CAS No. 121669-70-3
  • Cat. No. CS-W005556
  • Purity ≥95%
  • MDL No. MFCD05663855
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₁IN₂O₂
  • Molecular Weight 294.09
  • Synonym(s) tert-Butyl-4-iodo-1H-pyrazole-1-carboxylate
  • SMILES CC(C)(C)OC(=O)N1C=C(I)C=N1

Description

tert-Butyl 4-iodo-1H-pyrazole-1-carboxylate features a bench-stable pyrazole core functionalized with a reactive iodide at the 4-position, enabling direct coupling in cross-coupling reactions. The tert-butyl ester group offers enhanced solubility and stability during synthetic manipulations, facilitating efficient incorporation into complex molecular architectures.

Application

tert-Butyl 4-iodo-1H-pyrazole-1-carboxylate serves as a versatile building block for the synthesis of functionalized pyrazole scaffolds. The iodine substituent enables efficient palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura and Sonogashira couplings, facilitating rapid diversification. The tert-butyl carbamate group provides excellent stability under basic conditions and can be readily removed via acidolysis to yield the free amine. This reagent exhibits high bench stability, ease of purification, and broad compatibility with common functional groups, making it ideal for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Bristol-Myers Squibb Pharma Company Patent: EP946508 B1, 2009 ; Location in patent: Page/Page column 58 ;

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   44.12
  • LogP   2.2709
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   0

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