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CS-W001157 4
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3-Bromo-5-nitropyridin-4-amine

  • CAS No. 89284-05-9

  • Cat. No. CS-W006864
  • Purity≥96%
  • MDL No.MFCD01646057

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

3-Bromo-5-nitropyridin-4-amine|CS-W006864

Structure of 89284-05-9

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General Information

  • CAS No. 89284-05-9
  • Cat. No. CS-W006864
  • Purity ≥96%
  • MDL No. MFCD01646057
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄BrN₃O₂
  • Molecular Weight 218.01
  • Synonym(s) 4-AMino-3-nitro-5-broMopyridine
  • SMILES NC1=C(Br)C=NC=C1[N+]([O-])=O

Description

3-Bromo-5-nitropyridin-4-amine features a pyridine core functionalized with bromo, nitro, and amino groups at positions 3, 5, and 4 respectively. This trifunctional scaffold enables direct coupling in cross-coupling reactions, with the electron-deficient ring enhancing reactivity in palladium-catalyzed transformations. The amine group provides a handle for further derivatization, while the bromo moiety facilitates selective substitution under mild conditions.

Application

3-Bromo-5-nitropyridin-4-amine serves as a versatile building block for the synthesis of heterocyclic scaffolds in medicinal chemistry and agrochemical research. Its strategic placement of bromo and nitro groups enables sequential cross-coupling and reduction reactions, while the pyridine nitrogen offers coordination potential. The compound exhibits good bench stability and facilitates efficient functional group manipulation under standard conditions.

Synthesis

  • Route1

    References

    • Samumed, LLC; Hood, John; Kumar KC, Sunil; Wallace, David Mark Patent: US2013/296302 A1, 2013 ; Location in patent: Paragraph 0563 ;
  • Route2

    References

    • Pharmaceutical Bulletin, , vol. 4, p. 20,23
  • Route3
    • N-(3-bromopyridin-4-yl)nitramide|CS-0606849
      15367-14-3
    • ~%
    • In-stock
      3-Bromo-5-nitropyridin-4-amine|CS-W006864
      89284-05-9

    References

    • Polish Journal of Chemistry, , vol. 69, # 4 p. 605 - 611

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   82.05
  • LogP   1.3345
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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