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CS-W001157 4
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Ethyl 4-nitro-1H-pyrrole-2-carboxylate

  • CAS No. 5930-92-7

  • Cat. No. CS-W005440
  • Purity≥98%
  • MDL No.MFCD00059927

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

Ethyl 4-nitro-1H-pyrrole-2-carboxylate|CS-W005440

Structure of 5930-92-7

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General Information

  • CAS No. 5930-92-7
  • Cat. No. CS-W005440
  • Purity ≥98%
  • MDL No. MFCD00059927
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈N₂O₄
  • Molecular Weight 184.15
  • Synonym(s) 4-Nitropyrrole-2-carboxylic Acid Ethyl Ester
  • SMILES O=C(C1=CC([N+]([O-])=O)=CN1)OCC

Description

Ethyl 4-nitro-1H-pyrrole-2-carboxylate features a pyrrole core bearing both an electron-deficient nitro group and a readily manipulable ester functionality. This dual-reactive architecture enables seamless integration into cross-coupling reactions and heterocyclic syntheses, delivering complex scaffolds with high regiocontrol under standard conditions.

Application

Ethyl 4-nitro-1H-pyrrole-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted pyrroles via selective reduction and functionalization. The nitro group facilitates electrophilic substitution at C5, while the ester moiety supports cross-coupling and hydrolysis reactions. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1
    • In-stock
      Glycine ethyl ester monohydrochloride|CS-W020007
      623-33-6
    • null|null
      181294-58-6
    • ~57%
    • In-stock
      Ethyl 4-nitro-1H-pyrrole-2-carboxylate|CS-W005440
      5930-92-7

    References

    • Nishiwaki, Nagatoshi; Ogihara, Takuma; Takami, Toshiko; Tamura, Mina; Ariga, Masahiro Journal of Organic Chemistry, 2004 , vol. 69, # 24 p. 8382 - 8386
  • Route2

    References

    • Lee; Coulter; Lown Journal of Organic Chemistry, 1988 , vol. 53, # 9 p. 1855 - 1859
  • Route3
    • 2,2,2-Trichloro-1-(4-nitro-1h-pyrrol-2-yl)ethan-1-one|CS-0267933
      53391-50-7
    • null|null
      64-17-5
    • ~70%
    • In-stock
      Ethyl 4-nitro-1H-pyrrole-2-carboxylate|CS-W005440
      5930-92-7

    References

    • BAYER HEALTHCARE AG Patent: WO2004/52852 A1, 2004 ; Location in patent: Page 31-32 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3259
Class : 8
Packing Group : Ⅲ
Hazard Statements : H318
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   85.23
  • LogP   1.0996
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   3

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