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CS-W001157 4
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1-(6-Chloro-pyridin-3-yl)-ethanone

  • CAS No. 55676-22-7

  • Cat. No. CS-D0744
  • Purity≥97%
  • MDL No.MFCD03407343

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

1-(6-Chloro-pyridin-3-yl)-ethanone|CS-D0744

Structure of 55676-22-7

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General Information

  • CAS No. 55676-22-7
  • Cat. No. CS-D0744
  • Purity ≥97%
  • MDL No. MFCD03407343
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆ClNO
  • Molecular Weight 155.58
  • Synonym(s) 5-Acetyl-2-chloropyridine1-(6-Chloro-3-pyridinyl)-1-ethanone
  • SMILES O=C(C)C1=CC=C(Cl)N=C1

Description

1-(6-Chloro-pyridin-3-yl)-ethanone features a chlorinated pyridine ring linked via a ketone to an acetyl group, enabling integration into diverse synthetic pathways. The electron-deficient pyridine moiety enhances reactivity in nucleophilic substitution and coupling reactions. This bench-stable compound serves as a key building block for pharmaceutical intermediates and functionalized heterocycles.

Application

1-(6-Chloro-pyridin-3-yl)-ethanone serves as a versatile building block in medicinal chemistry, enabling efficient construction of pyridine-based scaffolds. Its ketone functionality reacts readily with nucleophiles and participates in standard transformations such as reductive amination and Grignard additions. The 6-chloro substituent provides orthogonal reactivity for palladium-catalyzed coupling reactions, enhancing synthetic flexibility in API development. Bench-stable and amenable to straightforward purification, it functions effectively in multi-step syntheses requiring functional group compatibility.

Synthesis

  • Route1
    • Dimethyl 2-(6-chloronicotinoyl)malonate|CS-0678505
      923034-23-5
    • ~31%
    • In-stock
      1-(6-Chloro-pyridin-3-yl)-ethanone|CS-D0744
      55676-22-7

    References

    • KALYPSYS, INC. Patent: US2007/27184 A1, 2007 ; Location in patent: Page/Page column 17; 19 ; US 20070027184 A1
  • Route2

    References

    • Hajduk; Gomtsyan; Didomenico; Cowart; Bayburt; Solomon; Severin; Smith; Walter; Holzman; Stewart; McGaraughty; Jarvis; Kowaluk; Fesik Journal of Medicinal Chemistry, 2000 , vol. 43, # 25 p. 4781 - 4786
  • Route3

    References

    • Bioorganic and Medicinal Chemistry, , vol. 13, # 11 p. 3705 - 3720

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   29.96
  • LogP   1.9376
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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