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CS-W001157 4
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Benzothiazole-5-carboxylic acid

  • CAS No. 68867-17-4

  • Cat. No. CS-D0851
  • Purity≥98%
  • MDL No.MFCD06796380

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

Benzothiazole-5-carboxylic acid|CS-D0851

Structure of 68867-17-4

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General Information

  • CAS No. 68867-17-4
  • Cat. No. CS-D0851
  • Purity ≥98%
  • MDL No. MFCD06796380
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅NO₂S
  • Molecular Weight 179.20
  • Synonym(s) benzo[d]thiazole-5-carboxylic acid
  • SMILES O=C(C1=CC=C(SC=N2)C2=C1)O

Description

Benzothiazole-5-carboxylic acid features a rigid heteroaromatic core with a carboxylic acid group at the 5-position, enabling direct conjugation in bioactive molecule design. This scaffold exhibits enhanced solubility and metabolic stability compared to analogous systems, facilitating integration into pharmaceutical intermediates and functional materials.

Application

Benzothiazole-5-carboxylic acid serves as a versatile building block for heterocyclic synthesis, enabling direct functionalization at the 5-position through standard carboxylic acid transformations. Its stability under ambient conditions and compatibility with amide coupling, esterification, and decarboxylation protocols facilitate efficient access to pharmaceutical intermediates and bioactive scaffolds. Functions as a key motif in kinase inhibitor and antitumor agent development.

Synthesis

  • Route1

    References

    • MEMORY PHARMACEUTICALS CORPORATION Patent: WO2005/92890 A2, 2005 ; Location in patent: Page/Page column 70-71 ; WO 2005/092890 A2
  • Route2

    References

    • Walker, Daniel P.; Wishka, Donn G.; Piotrowski, David W.; Jia, Shaojuan; Reitz, Steven C.; Yates, Karen M.; Myers, Jason K.; Vetman, Tatiana N.; Margolis, Brandon J.; Jacobsen, E. Jon; Acker, Brad A.; Groppi, Vincent E.; Wolfe, Mark L.; Thornburgh, Bruce A.; Tinholt, Paula M.; Cortes-Burgos, Luz A.; Walters, Rodney R.; Hester, Matthew R.; Seest, Eric P.; Dolak, Lester A.; Han, Fusen; Olson, Barbara A.; Fitzgerald, Laura; Staton, Brian A.; Raub, Thomas J.; Hajos, Mihaly; Hoffmann, William E.; Li, Kai S.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Wong, Erik H.F.; Rogers, Bruce N. Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 24 p. 8219 - 8248
  • Route3

    References

    • WO2003/87098 A1, ; Page/Page column 67 ;

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   50.19
  • LogP   1.9945
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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