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CS-W001157 4
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2-Chloro-6-methoxybenzo[d]thiazole

  • CAS No. 2605-14-3

  • Cat. No. CS-W015634
  • Purity≥97%
  • MDL No.MFCD00671510

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

2-Chloro-6-methoxybenzo[d]thiazole|CS-W015634

Structure of 2605-14-3

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General Information

  • CAS No. 2605-14-3
  • Cat. No. CS-W015634
  • Purity ≥97%
  • MDL No. MFCD00671510
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆ClNOS
  • Molecular Weight 199.65
  • Synonym(s) Chloromethoxybenzothiazole
  • SMILES COC1=CC=C2N=C(Cl)SC2=C1

Description

2-Chloro-6-methoxybenzo[d]thiazole features a fused benzothiazole core with strategically positioned electron-withdrawing chlorine and electron-donating methoxy groups, enhancing its reactivity in cross-coupling and electrophilic substitution reactions. This bench-stable heterocycle integrates readily into complex molecular architectures, offering predictable regioselectivity under standard conditions.

Application

2-Chloro-6-methoxybenzo[d]thiazole serves as a versatile building block in medicinal chemistry, enabling efficient construction of biologically relevant heterocyclic scaffolds. The chloro group facilitates palladium-catalyzed cross-coupling reactions, while the methoxy substituent enhances solubility and modulates electronic properties. Its stability under standard reaction conditions and compatibility with diverse functional groups make it a practical choice for synthesizing complex molecules in drug discovery workflows.

Synthesis

  • Route1

    References

    • Suzuki, Nobutaka; Nomoto, Tateo; Toya, Yoshiaki; Kanamori, Norio; Yoda, Binkoh; Saeki, Akio Bioscience, Biotechnology, and Biochemistry, 1993 , vol. 57, # 9 p. 1561 - 1562
  • Route2

    References

    • Boehringer Mannheim GmbH Patent: US4826989 A1, 1989 ;
  • Route3
    • 2-Hydrazono-6-methoxy-2,3-dihydrobenzo[d]thiazole|CS-0073626
      20174-70-3
    • ~%
    • In-stock
      2-Chloro-6-methoxybenzo[d]thiazole|CS-W015634
      2605-14-3

    References

    • Ouyang, Liang; Huang, Yuhui; Zhao, Yuwei; He, Gu; Xie, Yongmei; Liu, Jie; He, Jun; Liu, Bo; Wei, Yuquan Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 9 p. 3044 - 3049

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-H319
Precautionary Statements : P264-P270-P280-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   22.12
  • LogP   2.9583
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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