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CS-W001157 4
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6-Methyl-1,3-benzothiazole

  • CAS No. 2942-15-6

  • Cat. No. CS-0308786
  • Purity≥96%
  • MDL No.MFCD01325556

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

6-Methyl-1,3-benzothiazole|CS-0308786

Structure of 2942-15-6

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General Information

  • CAS No. 2942-15-6
  • Cat. No. CS-0308786
  • Purity ≥96%
  • MDL No. MFCD01325556
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇NS
  • Molecular Weight 149.21
  • Synonym(s) 6-Methylbenzothiazole
  • SMILES CC1=CC2=C(C=C1)N=CS2

Description

6-Methyl-1,3-benzothiazole serves as a key heterocyclic scaffold in medicinal chemistry and materials science. This bench-stable, electron-rich compound features a methyl group at the 6-position, enhancing its lipophilicity and metabolic stability. The fused benzothiazole core provides rigidity and favorable π-stacking interactions, enabling effective integration into bioactive molecules and functional organic semiconductors.

Application

6-Methyl-1,3-benzothiazole serves as a versatile heterocyclic building block in medicinal chemistry and materials science. Its electron-rich aromatic core enables efficient functionalization via electrophilic substitution and palladium-catalyzed coupling reactions. The methyl group enhances metabolic stability and modulates electronic properties, while the benzothiazole scaffold provides robustness under standard reaction conditions. Bench-stable and readily purified by column chromatography, it facilitates scalable synthesis of bioactive compounds and advanced organic semiconductors.

Synthesis

  • Route1

    References

    • Itoh, Takashi; Matsuya, Yuji; Nagata, Kazuhiro; Ohsawa, Akio Chemical and Pharmaceutical Bulletin, 1997 , vol. 45, # 9 p. 1547 - 1549
  • Route2
    • N-(6-Methyl-1,3-Benzothiazol-2-yl)acetamide|CS-0766571
      20600-51-5
    • ~%
    • In-stock
      6-Methyl-1,3-benzothiazole|CS-0308786
      2942-15-6

    References

    • Nitta, Aiko; Fujii, Hideaki; Sakami, Satoshi; Nishimura, Yutaka; Ohyama, Tomofumi; Satoh, Mikiya; Nakaki, Junko; Satoh, Shiho; Inada, Chifumi; Kozono, Hideki; Kumagai, Hiroki; Shimamura, Masahiro; Fukazawa, Tominaga; Kawai, Hideki Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 20 p. 5435 - 5438
  • Route3

    References

    • Baldwin,J.E. et al. Journal of Organic Chemistry, 1977 , vol. 42, p. 4142 - 4144

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   12.89
  • LogP   2.60472
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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