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CS-W001157 4
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Methyl 3-hydroxy-2-nitrobenzoate

  • CAS No. 89942-77-8

  • Cat. No. CS-W003695
  • Purity≥96%
  • MDL No.MFCD09951956

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

Methyl 3-hydroxy-2-nitrobenzoate|CS-W003695

Structure of 89942-77-8

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General Information

  • CAS No. 89942-77-8
  • Cat. No. CS-W003695
  • Purity ≥96%
  • MDL No. MFCD09951956
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇NO₅
  • Molecular Weight 197.14
  • Synonym(s) Benzoic acid, 3-hydroxy-2-nitro-, methyl ester
  • SMILES O=C(OC)C1=CC=CC(O)=C1[N+]([O-])=O

Description

Methyl 3-hydroxy-2-nitrobenzoate features a strategically positioned hydroxyl group flanking a nitro substituent on the aromatic ring, enabling direct participation in cross-coupling and derivatization reactions. This bench-stable ester integrates readily into synthetic sequences requiring ortho-functionalized building blocks.

Application

Methyl 3-hydroxy-2-nitrobenzoate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized aromatic scaffolds. The ortho-nitro and hydroxyl groups provide complementary reactivity for selective transformations, including reduction, coupling, and cyclization reactions. Its bench-stable nature and compatibility with standard purification methods make it well-suited for use in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • PFIZER PRODUCTS INC. Patent: WO2007/125405 A2, 2007 ; Location in patent: Page/Page column 24; 72-73 ; WO 2007/125405 A2
  • Route2
    • null|null
      67-56-1
    • In-stock
      3-Hydroxy-2-nitrobenzoic acid|CS-D1622
      602-00-6
    • ~94%
    • In-stock
      Methyl 3-hydroxy-2-nitrobenzoate|CS-W003695
      89942-77-8

    References

    • Gavai, Ashvinikumar V.; DeLucca, George V.; O'Malley, Daniel; Gill, Patrice; Quesnelle, Claude A.; Fink, Brian E.; Zhao, Yufen; Lee, Francis Y. Patent: US2014/87992 A1, 2014 ; Location in patent: Paragraph 0314-0315 ;
  • Route3
    • In-stock
      3-Hydroxy-2-nitrobenzoic acid|CS-D1622
      602-00-6
    • null|null
      18107-18-1
    • ~97%
    • In-stock
      Methyl 3-hydroxy-2-nitrobenzoate|CS-W003695
      89942-77-8

    References

    • Tipparaju, Suresh K.; Joyasawal, Sipak; Pieroni, Marco; Kaiser, Marcel; Brun, Reto; Kozikowski, Alan P. Journal of Medicinal Chemistry, 2008 , vol. 51, # 23 p. 7344 - 7347

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   89.67
  • LogP   1.087
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   2

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