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Methyl 2-cyano-3-nitrobenzoate

  • CAS No. 77326-46-6

  • Cat. No. CS-0042729
  • Purity≥95%
  • MDL No.None

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

Methyl 2-cyano-3-nitrobenzoate|CS-0042729

Structure of 77326-46-6

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General Information

  • CAS No. 77326-46-6
  • Cat. No. CS-0042729
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆N₂O₄
  • Molecular Weight 206.15
  • Synonym(s) Benzoic acid, 2-cyano-3-nitro-, methyl ester
  • SMILES O=C(OC)C1=CC=CC([N+]([O-])=O)=C1C#N

Description

Methyl 2-cyano-3-nitrobenzoate features a conjugated cyano and nitro group flanking a methyl ester, delivering high reactivity in transition-metal-catalyzed couplings. This electron-deficient aromatic scaffold enables efficient incorporation into complex heterocycles and serves as a robust building block for pharmaceutical intermediates under standard conditions.

Application

Methyl 2-cyano-3-nitrobenzoate serves as a versatile synthon in heterocyclic synthesis, enabling efficient access to substituted quinoline and benzimidazole scaffolds via tandem cyclization reactions. The ortho-difunctionalized aromatic core exhibits excellent bench stability and facilitates straightforward purification. Its dual electron-withdrawing groups (cyano and nitro) enhance electrophilicity for nucleophilic substitution and enable compatibility with palladium-catalyzed coupling protocols. Functions reliably in multi-step sequences requiring functional group tolerance and predictable reactivity.

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

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Computational Chemistry Data

  • TPSA   93.23
  • LogP   1.25308
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   2

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