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CS-W001157 4
Total: USD 88.00

2-Chloro-N,N-dimethylpyridin-4-amine

  • CAS No. 59047-70-0

  • Cat. No. CS-W001602
  • Purity≥98%
  • MDL No.MFCD09031034

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

2-Chloro-N,N-dimethylpyridin-4-amine|CS-W001602

Structure of 59047-70-0

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General Information

  • CAS No. 59047-70-0
  • Cat. No. CS-W001602
  • Purity ≥98%
  • MDL No. MFCD09031034
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₉ClN₂
  • Molecular Weight 156.61
  • Synonym(s) 2-Chloro-4-(dimethylamino)pyridine
  • SMILES CN(C1=CC(Cl)=NC=C1)C

Description

2-Chloro-N,N-dimethylpyridin-4-amine features a pyridine core with a chloro group at the 2-position and N,N-dimethyl substitution at the 4-position, delivering enhanced electrophilicity and stability. This configuration enables efficient coupling in cross-coupling reactions and facilitates incorporation into functionalized heterocycles under mild conditions.

Application

2-Chloro-N,N-dimethylpyridin-4-amine serves as a versatile building block in medicinal chemistry, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. The chloropyridine moiety exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the dimethylamino group enhances solubility and modulates electronic properties. Bench-stable and readily purified by column chromatography, it functions as a key intermediate in the synthesis of heterocyclic scaffolds relevant to pharmaceutical development.

Synthesis

  • Route1
    • N,N-Dimethylpyridin-4-amine Vonoprazan Impurity|CS-0167023
      1122-58-3
    • ~87%
    • In-stock
      2-Chloro-N,N-dimethylpyridin-4-amine|CS-W001602
      59047-70-0

    References

    • Cuperly, David; Gros, Philippe; Fort, Yves Journal of Organic Chemistry, 2002 , vol. 67, # 1 p. 238 - 241
  • Route2
    • In-stock
      2,4-Dichloropyridine|CS-W004774
      26452-80-2
    • null|null
      124-40-3
    • ~88%
    • In-stock
      2-Chloro-N,N-dimethylpyridin-4-amine|CS-W001602
      59047-70-0

    References

    • Schlosser, Manfred; Bobbio, Carla; Rausis, Thierry Journal of Organic Chemistry, 2005 , vol. 70, # 7 p. 2494 - 2502
  • Route3

    References

    • KALYPSYS, INC. Patent: WO2009/29617 A1, 2009 ; Location in patent: Page/Page column 47 ; WO 2009/029617 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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   16.13
  • LogP   1.801
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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