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CS-W001157 4
Total: USD 88.00

2-Chloro-3-methoxy-5-nitropyridine

  • CAS No. 75711-00-1

  • Cat. No. CS-W005232
  • Purity≥98%
  • MDL No.MFCD06658397

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

2-Chloro-3-methoxy-5-nitropyridine|CS-W005232

Structure of 75711-00-1

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General Information

  • CAS No. 75711-00-1
  • Cat. No. CS-W005232
  • Purity ≥98%
  • MDL No. MFCD06658397
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅ClN₂O₃
  • Molecular Weight 188.57
  • Synonym(s) 2-chloro-3-(methyloxy)-5-nitropyridine
  • SMILES O=[N+](C1=CN=C(Cl)C(OC)=C1)[O-]

Description

2-Chloro-3-methoxy-5-nitropyridine features a strategically positioned nitro group that enhances electrophilic reactivity, while the methoxy substituent improves solubility and stability. This electron-deficient pyridine scaffold enables efficient coupling in transition-metal-catalyzed reactions, serving as a key intermediate in the synthesis of functionalized heterocycles for pharmaceutical and agrochemical applications.

Application

2-Chloro-3-methoxy-5-nitropyridine serves as a versatile building block in heterocyclic synthesis, enabling efficient functionalization at the 2-position via palladium-catalyzed cross-coupling. The chloro group exhibits high reactivity in Suzuki, Stille, and Negishi reactions, while the methoxy and nitro substituents provide orthogonal handles for further modification. Bench-stable and compatible with standard purification methods, it facilitates the construction of complex pyridine-based scaffolds relevant to medicinal chemistry and agrochemical development.

Synthesis

  • Route1
    • 3-Methoxy-5-nitro-pyridin-2-ol|CS-0209087
      75710-99-5
    • ~77%
    • In-stock
      2-Chloro-3-methoxy-5-nitropyridine|CS-W005232
      75711-00-1

    References

    • Gruenenthal GmbH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo Patent: US2013/29962 A1, 2013 ; Location in patent: Paragraph 0983 ;
  • Route2

    References

    • WO2013/13815 A1, ; WO 2013/013815 A1

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   65.26
  • LogP   1.6518
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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