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CS-W001157 4
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2-Hydroxy-6-nitrobenzoic acid

  • CAS No. 601-99-0

  • Cat. No. CS-W002157
  • Purity≥98%
  • MDL No.MFCD00031281

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

2-Hydroxy-6-nitrobenzoic acid|CS-W002157

Structure of 601-99-0

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General Information

  • CAS No. 601-99-0
  • Cat. No. CS-W002157
  • Purity ≥98%
  • MDL No. MFCD00031281
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅NO₅
  • Molecular Weight 183.12
  • Synonym(s) 6-Nitrosalicylic Acid
  • SMILES O=C(O)C1=C([N+]([O-])=O)C=CC=C1O

Description

2-Hydroxy-6-nitrobenzoic acid features a strategically positioned nitro group and hydroxyl moiety on adjacent carbons of the aromatic ring, enhancing its reactivity in electrophilic substitution and enabling efficient coupling reactions. This ortho-functionalized scaffold serves as a key intermediate in the synthesis of fluorescent probes and bioactive heterocycles under standard conditions.

Application

2-Hydroxy-6-nitrobenzoic acid serves as a versatile building block for heterocyclic synthesis, enabling efficient access to substituted quinoline and benzoxazole scaffolds. Its ortho-hydroxyl and nitro groups facilitate directed metalation and electrophilic substitution, while the carboxylic acid supports derivatization via amide or ester formation. The compound exhibits good bench stability and is readily purified by recrystallization, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • Makhlynets, Olga V.; Das, Parthapratim; Taktak, Sonia; Flook, Margaret; Mas-Balleste, Ruben; Rybak-Akimova, Elena V.; Que Jr., Lawrence Chemistry - A European Journal, 2009 , vol. 15, # 47 p. 13171 - 13180
  • Route2

    References

    • Goldberg; Walker Journal of the Chemical Society, 1953 , p. 2049,2051
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    • 2-Hydroxy-6-nitrobenzoic acid|CS-W002157
      601-99-0

    References

    • Mehta; Ayyar Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1939 , vol. 8/3, p. 176,179

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   100.67
  • LogP   0.9986
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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