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5-Nitrobenzo[b]thiophene-2-carboxylic acid

  • CAS No. 6345-55-7

  • Cat. No. CS-0102214
  • Purity≥95%
  • MDL No.MFCD01159700

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

5-Nitrobenzo[b]thiophene-2-carboxylic acid|CS-0102214

Structure of 6345-55-7

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General Information

  • CAS No. 6345-55-7
  • Cat. No. CS-0102214
  • Purity ≥95%
  • MDL No. MFCD01159700
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅NO₄S
  • Molecular Weight 223.21
  • Synonym(s) 5-Nitro-1-benzothiophene-2-carboxylic acid
  • SMILES O=C(C1=CC2=CC([N+]([O-])=O)=CC=C2S1)O

Description

5-Nitrobenzo[b]thiophene-2-carboxylic acid features a fused thiophene core with electron-withdrawing nitro and carboxylic acid groups positioned for orthogonal reactivity. This arrangement enables direct integration into heterocyclic scaffolds, offering enhanced solubility and stability under standard conditions.

Application

5-Nitrobenzo[b]thiophene-2-carboxylic acid serves as a versatile building block for heterocyclic synthesis, offering a rigid, electron-deficient scaffold with orthogonal functional handles. The carboxylic acid group enables direct derivatization via amide or ester formation, while the nitro substituent supports subsequent reduction and coupling reactions. Its stability under standard bench conditions and compatibility with common cross-coupling protocols facilitate efficient access to complex molecular architectures in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Cai, Jin; Zhang, Shaoning; Zheng, Ming; Wu, Xiaoqing; Chen, Junqing; Ji, Min Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 2 p. 806 - 810
  • Route2

    References

    • Pessoa-Mahana, Hernan; Kosche C., Johann; Ron H., Nadia; Recabarren-Gajardo, Gonzalo; Saitz B., Claudio; Araya-Maturana, Ramiro; Pessoa-Mahana, C. David Heterocycles, 2008 , vol. 75, # 8 p. 1913 - 1929
  • Route3

    References

    • Justus Liebigs Annalen der Chemie, , vol. 527, p. 83,101 Journal of the American Chemical Society, , vol. 77, p. 5539,5941

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   80.44
  • LogP   2.5077
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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