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Methyl 5-cyano-1H-pyrrole-2-carboxylate

  • CAS No. 937-19-9

  • Cat. No. CS-0150820
  • Purity≥95%
  • MDL No.MFCD12924294

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

Methyl 5-cyano-1H-pyrrole-2-carboxylate|CS-0150820

Structure of 937-19-9

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General Information

  • CAS No. 937-19-9
  • Cat. No. CS-0150820
  • Purity ≥95%
  • MDL No. MFCD12924294
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆N₂O₂
  • Molecular Weight 150.13
  • Synonym(s) 1H-Pyrrole-2-carboxylicacid,5-cyano-,methylester(9CI)
  • SMILES COC(=O)C1=CC=C(C#N)N1

Description

Methyl 5-cyano-1H-pyrrole-2-carboxylate features a conjugated pyrrole core with strategically positioned electron-withdrawing cyano and ester groups. This combination enhances electrophilicity at the C2 position, enabling efficient coupling in transition-metal-catalyzed reactions. The molecule exhibits bench-stable handling characteristics and integrates readily into heterocyclic synthesis workflows.

Application

Methyl 5-cyano-1H-pyrrole-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to pyrrole-based scaffolds through standard functional group manipulations. The cyano and ester groups provide orthogonal reactivity for nucleophilic addition, reduction, and coupling reactions, facilitating downstream derivatization. Its bench-stable nature and compatibility with common reaction conditions make it well-suited for medicinal chemistry campaigns and process-scale applications.

Synthesis

  • Route1
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      848499-68-3
    • ~%
    • In-stock
      Methyl 5-cyano-1H-pyrrole-2-carboxylate|CS-0150820
      937-19-9

    References

    • ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2005/26149 A1, 2005 ; Location in patent: Page/Page column 108 ; WO 2005/026149 A1
  • Route2
    • In-stock
      Methyl 1H-pyrrole-2-carboxylate|CS-W013518
      1193-62-0
    • null|null
      1189-71-5
    • ~23%
    • In-stock
      Methyl 5-cyano-1H-pyrrole-2-carboxylate|CS-0150820
      937-19-9

    References

    • Pinter, Thomas; Simhadri, Chakravarthi; Hof, Fraser Journal of Organic Chemistry, 2013 , vol. 78, # 10 p. 4642 - 4648
  • Route3

    References

    • Loader, Charles E.; Anderson, Hugh J. Canadian Journal of Chemistry, 1981 , vol. 59, p. 2673 - 2676

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   65.88
  • LogP   0.67298
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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