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CS-W001157 4
Total: USD 88.00

6-Nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide

  • CAS No. 22952-24-5

  • Cat. No. CS-W018643
  • Purity≥95%
  • MDL No.MFCD00110677

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

6-Nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide|CS-W018643

Structure of 22952-24-5

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General Information

  • CAS No. 22952-24-5
  • Cat. No. CS-W018643
  • Purity ≥95%
  • MDL No. MFCD00110677
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄N₂O₅S
  • Molecular Weight 228.18
  • Synonym(s) 6-Nitrosaccharin
  • SMILES C1=C([N+](=O)[O-])C=CC2=C1[S](NC2=O)(=O)=O

Description

6-Nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide is a potent, bench-stable heterocyclic electrophile featuring a strongly electron-deficient core. This compound integrates a nitro group at the para position relative to the isothiazolone ring, enhancing reactivity for conjugate addition and targeted protein labeling. The sulfone moiety ensures high stability under ambient conditions, enabling reliable use in chemical biology workflows.

Application

6-Nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient access to bioactive scaffolds. Its electron-deficient core facilitates nucleophilic substitution reactions and exhibits favorable bench stability. The molecule's dual functional groups—nitro and sulfonamide—support orthogonal reactivity, aiding in the construction of complex molecular architectures through established coupling protocols.

Synthesis

  • Route1

    References

    • Gener, Nahit; Demir, Dudu; Sonmez, Fatih; Kucukislamoglu, Mustafa Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 9 p. 2811 - 2821
  • Route2
    • null|null
      309735-34-0
    • ~45%
    • In-stock
      6-Nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide|CS-W018643
      22952-24-5

    References

    • Serebryakov; Kislitsin; Semenov; Zlotin Synthesis, 2001 , # 11 p. 1659 - 1664
  • Route3
    • null|null
      515884-30-7
    • ~35%
    • In-stock
      6-Nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide|CS-W018643
      22952-24-5

    References

    • Serebryakov; Zlotin Russian Chemical Bulletin, 2002 , vol. 51, # 8 p. 1549 - 1555

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H315-H319-H332-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   106.38
  • LogP   0.0269
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   1

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