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CS-W001157 4
Total: USD 88.00

Methyl 2-nitrobenzoate

  • CAS No. 606-27-9

  • Cat. No. CS-0128782
  • Purity≥98%
  • MDL No.MFCD00007136

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

Methyl 2-nitrobenzoate|CS-0128782

Structure of 606-27-9

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General Information

  • CAS No. 606-27-9
  • Cat. No. CS-0128782
  • Purity ≥98%
  • MDL No. MFCD00007136
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇NO₄
  • Molecular Weight 181.15
  • Synonym(s) 2-Nitrobenzoic Acid Methyl Ester
  • SMILES O=C(OC)C1=CC=CC=C1[N+]([O-])=O

Description

Methyl 2-nitrobenzoate features a para-nitro group flanking a methyl ester on a benzene ring, delivering enhanced electron-withdrawing character. This configuration enables efficient participation in nucleophilic aromatic substitution and facilitates coupling reactions under mild conditions. The compound exhibits bench-stable handling properties and integrates readily into synthetic sequences requiring controlled reactivity.

Application

Methyl 2-nitrobenzoate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted benzimidazoles and other heterocyclic scaffolds via cyclization protocols. Its ortho-nitro group facilitates directed metalation and subsequent functionalization, while the ester moiety offers compatibility with standard reduction, coupling, and nucleophilic substitution reactions. The compound exhibits excellent bench stability and is readily purified by recrystallization or flash chromatography, making it well-suited for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      2-Nitrobenzoic acid|CS-W020072
      552-16-9
    • ~89%
    • In-stock
      Methyl 2-nitrobenzoate|CS-0128782
      606-27-9

    References

    • Zaheer, Muhammad; Zia-Ur-Rehman, Muhammad; Rahman, Salma; Ahmed, Naveed; Chaudhary, Muhammad Nawaz Journal of the Chilean Chemical Society, 2012 , vol. 57, # 4 p. 1492 - 1496
  • Route2
    • null|null
      75-91-2
    • In-stock
      2-Nitrobenzaldehyde|CS-W007454
      552-89-6
    • ~65%
    • In-stock
      Methyl 2-nitrobenzoate|CS-0128782
      606-27-9

    References

    • Li, Pan; Zhao, Jingjing; Lang, Rui; Xia, Chungu; Li, Fuwei Tetrahedron Letters, 2014 , vol. 55, # 2 p. 390 - 393
  • Route3
    • null|null
      134-20-3
    • ~99%
    • In-stock
      Methyl 2-nitrobenzoate|CS-0128782
      606-27-9

    References

    • Kol, Moshe; Rozen, Shlomo Journal of the Chemical Society, Chemical Communications, 1991 , # 8 p. 567 - 568

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   69.44
  • LogP   1.3814
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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