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CS-W001157 4
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Dimethyl nitromalonate

  • CAS No. 5437-67-2

  • Cat. No. CS-0061797
  • Purity≥95%
  • MDL No.MFCD00010228

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

Dimethyl nitromalonate|CS-0061797

Structure of 5437-67-2

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General Information

  • CAS No. 5437-67-2
  • Cat. No. CS-0061797
  • Purity ≥95%
  • MDL No. MFCD00010228
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₇NO₆
  • Molecular Weight 177.11
  • Synonym(s) dimethyl nitropropanedioate
  • SMILES COC(=O)C(C(=O)OC)[N+](=O)[O-]

Description

Dimethyl nitromalonate features a highly electrophilic β-nitro carbonyl system, enabling efficient Michael additions and cycloadditions. This bench-stable diester integrates readily into synthetic sequences requiring controlled carbon-carbon bond formation, particularly in heterocycle synthesis and natural product derivatization.

Application

Dimethyl nitromalonate serves as a versatile diester building block in synthetic organic chemistry, enabling efficient access to α-nitro carboxylic acid derivatives and heterocyclic scaffolds. Its enhanced electrophilicity at the β-carbon facilitates nucleophilic addition reactions, including Michael additions and cycloadditions, with high functional group tolerance. The molecule exhibits excellent bench stability and ease of purification, making it well-suited for multi-step synthesis and scale-up applications.

Synthesis

  • Route1

    References

    • Recueil des Travaux Chimiques des Pays-Bas, , vol. 8, p. 285
  • Route2
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      42065-96-3
    • ~%
    • In-stock
      Dimethyl nitromalonate|CS-0061797
      5437-67-2

    References

    • Chemische Berichte, , vol. 32, p. 1781
  • Route3
    • Dimethyl 2-(hydroxyimino)malonate|CS-0115544
      42937-74-6
    • ~%
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      3298-40-6
    • null|null
      65390-51-4
    • In-stock
      Dimethyl nitromalonate|CS-0061797
      5437-67-2

    References

    • Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, , vol. 137, p. 198 Bulletin de la Societe Chimique de France, , vol. <3> 29, p. 965

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-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   95.74
  • LogP   -1.0223
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   3

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