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Methyl 4-iodo-1-methyl-1H-pyrazole-3-carboxylate

  • CAS No. 75092-25-0

  • Cat. No. CS-0041306
  • Purity≥98%
  • MDL No.MFCD19703827

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

Methyl 4-iodo-1-methyl-1H-pyrazole-3-carboxylate|CS-0041306

Structure of 75092-25-0

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General Information

  • CAS No. 75092-25-0
  • Cat. No. CS-0041306
  • Purity ≥98%
  • MDL No. MFCD19703827
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₇IN₂O₂
  • Molecular Weight 266.04
  • Synonym(s) None
  • SMILES O=C(C1=NN(C)C=C1I)OC

Description

Methyl 4-iodo-1-methyl-1H-pyrazole-3-carboxylate features a reactive iodine handle at the 4-position, enabling efficient cross-coupling transformations. The electron-deficient pyrazole core enhances stability and facilitates selective functionalization. This bench-stable reagent integrates seamlessly into synthetic workflows requiring heterocyclic building blocks with orthogonal reactivity.

Application

Methyl 4-iodo-1-methyl-1H-pyrazole-3-carboxylate serves as a versatile building block for transition-metal-catalyzed cross-coupling reactions, enabling efficient access to substituted pyrazole scaffolds. The iodide group facilitates palladium-catalyzed coupling with aryl, heteroaryl, and alkenyl boranes or stannanes under standard conditions. Its methyl ester functionality offers stability and compatibility with common protecting group strategies. The molecule exhibits robust bench stability and is readily purified by flash chromatography, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Vasilevskii, S. F.; Shvartsberg, M. S. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1980 , vol. 29, # 5 p. 778 - 784 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1980 , # 5 p. 1071 - 1077

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   0.8113
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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