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CS-W001157 4
Total: USD 88.00

2,6-difluoro-3-nitropyridine

  • CAS No. 58602-02-1

  • Cat. No. CS-W000551
  • Purity≥96%
  • MDL No.MFCD11044323

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

2,6-difluoro-3-nitropyridine|CS-W000551

Structure of 58602-02-1

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General Information

  • CAS No. 58602-02-1
  • Cat. No. CS-W000551
  • Purity ≥96%
  • MDL No. MFCD11044323
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₂F₂N₂O₂
  • Molecular Weight 160.08
  • Synonym(s) 2,6-Difluor-3-nitropyridin
  • SMILES [O-][N+](=O)c1ccc(F)nc1F

Description

2,6-Difluoro-3-nitropyridine features a trifunctional pyridine core with electron-withdrawing fluorine and nitro groups positioned for orthogonal reactivity. This bench-stable scaffold enables direct coupling in late-stage functionalization, offering high regioselectivity in cross-coupling and nucleophilic substitution workflows.

Application

2,6-Difluoro-3-nitropyridine serves as a versatile building block in medicinal chemistry, enabling regioselective functionalization at the C5 position via nucleophilic substitution. Its electron-deficient pyridine core enhances reactivity toward amines and thiols, facilitating the construction of key heterocyclic scaffolds. Bench-stable and readily purified by column chromatography, it supports scalable synthesis of API intermediates and advanced intermediates in drug discovery workflows.

Synthesis

  • Route1

    References

    • Shackelford, Scott A.; Anderson, Mark B.; Christie, Lance C.; Goetzen, Thomas; Guzman, Mark C.; Hananel, Martha A.; Kornreich, Wayne D.; Li, Haitao; Pathak, Ved P.; Rabinovich, Alex K.; Rajapakse, Ranjan J.; Truesdale, Larry K.; Tsank, Stella M.; Vazir, Haresh N. Journal of Organic Chemistry, 2003 , vol. 68, # 2 p. 267 - 275
  • Route2
    • In-stock
      2,6-Difluoropyridine|CS-W013627
      1513-65-1
    • null|null
      7664-93-9
    • ~72%
    • In-stock
      2,6-difluoro-3-nitropyridine|CS-W000551
      58602-02-1

    References

    • Simoneau, Bruno Patent: US2002/28807 A1, 2002 ;
  • Route3

    References

    • Radl, Stanislav; Hradil, Pavel Collection of Czechoslovak Chemical Communications, 1991 , vol. 56, # 11.1 p. 2420 - 2429

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   56.03
  • LogP   1.268
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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