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CS-W001157 4
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2-Bromobenzothiazole-6-carboxylic acid methyl ester

  • CAS No. 1024583-33-2

  • Cat. No. CS-W008855
  • Purity≥97%
  • MDL No.MFCD16660646

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

2-Bromobenzothiazole-6-carboxylic acid methyl ester|CS-W008855

Structure of 1024583-33-2

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General Information

  • CAS No. 1024583-33-2
  • Cat. No. CS-W008855
  • Purity ≥97%
  • MDL No. MFCD16660646
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆BrNO₂S
  • Molecular Weight 272.12
  • Synonym(s) Methyl 2-bromobenzo[d]thiazole-6-carboxylate; 6-Benzothiazolecarboxylic acid, 2-bromo-, methyl ester
  • SMILES O=C(C1=CC=C2N=C(Br)SC2=C1)OC

Description

This methyl ester derivative integrates a brominated benzothiazole core with a carboxylic acid ester functionality, enabling direct use in cross-coupling reactions. The electron-deficient heterocycle and reactive ester group facilitate efficient C–C bond formation under palladium catalysis, offering a stable, bench-ready platform for synthesizing complex biaryl architectures.

Application

2-Bromobenzothiazole-6-carboxylic acid methyl ester serves as a versatile building block for the synthesis of bioactive heterocycles, enabling palladium-catalyzed cross-coupling reactions and functionalization at the carboxylate position. Its bromo substituent facilitates C–C bond formation under standard Suzuki or Stille conditions, while the methyl ester group offers straightforward hydrolysis to the corresponding carboxylic acid. The molecule exhibits good bench stability and compatibility with common protecting group strategies, making it suitable for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 18, # 7 p. 2324 - 2328
  • Route2
    • In-stock
      2-Bromobenzo[d]thiazole-6-carboxylic acid|CS-W005489
      22514-58-5
    • null|null
      18107-18-1
    • ~%
    • In-stock
      2-Bromobenzothiazole-6-carboxylic acid methyl ester|CS-W008855
      1024583-33-2

    References

    • US2011/152287 A1, ; Page/Page column 21 ;

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   39.19
  • LogP   2.8454
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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