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CS-W001157 4
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5-Nitrobenzo[d]thiazol-2-amine

  • CAS No. 73458-39-6

  • Cat. No. CS-W019456
  • Purity≥97%
  • MDL No.MFCD00160073

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

5-Nitrobenzo[d]thiazol-2-amine|CS-W019456

Structure of 73458-39-6

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General Information

  • CAS No. 73458-39-6
  • Cat. No. CS-W019456
  • Purity ≥97%
  • MDL No. MFCD00160073
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅N₃O₂S
  • Molecular Weight 195.20
  • Synonym(s) 5-NITRO-BENZOTHIAZOL-2-YLAMINE
  • SMILES NC1=NC2=CC([N+]([O-])=O)=CC=C2S1

Description

5-Nitrobenzo[d]thiazol-2-amine features a fused benzothiazole core bearing a nitro group at the 5-position and an amino function at the 2-position. This electron-deficient heterocycle integrates into bioactive scaffolds, enabling efficient coupling in cross-coupling reactions and serving as a key building block for fluorescent probes and pharmaceutical intermediates under standard conditions.

Application

5-Nitrobenzo[d]thiazol-2-amine serves as a versatile building block for heterocyclic synthesis, enabling efficient access to biologically relevant scaffolds. Its ortho-nitro and amino groups facilitate sequential functionalization, including palladium-catalyzed couplings and electrophilic substitutions. The molecule exhibits good bench stability and is readily purified by recrystallization, making it suitable for iterative synthetic workflows in medicinal chemistry and materials science.

Synthesis

  • Route1
    • null|null
      341036-35-9
    • ~95%
    • In-stock
      5-Nitrobenzo[d]thiazol-2-amine|CS-W019456
      73458-39-6

    References

    • Sedlak, Milos; Hanusek, Jiri; Holcapek, Michal; Sterba, Vijeslav Journal of Physical Organic Chemistry, 2001 , vol. 14, # 3 p. 187 - 195
  • Route2
    • null|null
      333741-82-5
    • ~88%
    • In-stock
      5-Nitrobenzo[d]thiazol-2-amine|CS-W019456
      73458-39-6

    References

    • MCR RESEARCH INC. Patent: WO2004/14885 A1, 2004 ; Location in patent: Page 34-35 ;
  • Route3
    • 2,4-Dinitro-1-thiocyanatobenzene|CS-0320868
      1594-56-5
    • ~65%
    • In-stock
      5-Nitrobenzo[d]thiazol-2-amine|CS-W019456
      73458-39-6

    References

    • Schulze, Juergen; Tanneberg, Hartmut; Matschiner, Hermann Zeitschrift fuer Chemie (Stuttgart, Germany), 1980 , vol. 20, # 12 p. 436 - 437

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
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   82.05
  • LogP   1.7867
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   1

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