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CS-W001157 4
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5-Nitropyridine-2(1H)-thione

  • CAS No. 2127-09-5

  • Cat. No. CS-0033780
  • Purity≥98%
  • MDL No.MFCD00030890

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

5-Nitropyridine-2(1H)-thione|CS-0033780

Structure of 2127-09-5

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General Information

  • CAS No. 2127-09-5
  • Cat. No. CS-0033780
  • Purity ≥98%
  • MDL No. MFCD00030890
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄N₂O₂S
  • Molecular Weight 156.16
  • Synonym(s) 5-Nitro-2-pyridyl Mercaptan
  • SMILES S=C1C=CC([N+]([O-])=O)=CN1

Description

5-Nitropyridine-2(1H)-thione features a conjugated heterocyclic core bearing both electron-deficient nitro and thione functionalities. This arrangement enables direct participation in transition metal-catalyzed cross-coupling reactions and facilitates coordination to metals in catalytic systems. The compound exhibits enhanced stability under standard bench conditions and displays favorable solubility in polar organic solvents for synthetic applications.

Application

5-Nitropyridine-2(1H)-thione serves as a versatile building block in heterocyclic synthesis, enabling efficient access to functionalized pyridine derivatives. Its dual nitro and thione functionalities facilitate nucleophilic substitution, metal-catalyzed coupling, and cyclization reactions under mild conditions. The compound exhibits good bench stability and is compatible with common protecting group strategies, making it valuable for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Bieniarz; Cornwell Tetrahedron Letters, 1993 , vol. 34, # 6 p. 939 - 942
  • Route2
    • null|null
      1309779-44-9
    • ~0%
    • In-stock
      5-Nitropyridine-2(1H)-thione|CS-0033780
      2127-09-5
    • null|null
      1309779-46-1

    References

    • Grayson, Elizabeth J.; Bernardes, Goncalo J. L.; Chalker, Justin M.; Boutureira, Omar; Koeppe, Julia R.; Davis, Benjamin G. Angewandte Chemie - International Edition, 2011 , vol. 50, # 18 p. 4127 - 4132
  • Route3
    • null|null
      67-56-1
    • null|null
      650608-81-4
    • ~0%
    • In-stock
      5-Nitropyridine-2(1H)-thione|CS-0033780
      2127-09-5
    • In-stock
      Methyl β-D-glucopyranoside|CS-0064651
      709-50-2

    References

    • Niemiec-Cyganek; Szeja Polish Journal of Chemistry, 2003 , vol. 77, # 8 p. 969 - 973

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   58.93
  • LogP   1.65239
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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