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CS-W001157 4
Total: USD 88.00

2-Chloro-6-(trifluoromethyl)nicotinonitrile

  • CAS No. 386704-06-9

  • Cat. No. CS-W008691
  • Purity≥98%
  • MDL No.MFCD01862660

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

2-Chloro-6-(trifluoromethyl)nicotinonitrile|CS-W008691

Structure of 386704-06-9

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General Information

  • CAS No. 386704-06-9
  • Cat. No. CS-W008691
  • Purity ≥98%
  • MDL No. MFCD01862660
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₂ClF₃N₂
  • Molecular Weight 206.55
  • Synonym(s) None
  • SMILES N#CC1=C(Cl)N=C(C(F)(F)F)C=C1

Description

2-Chloro-6-(trifluoromethyl)nicotinonitrile features a trifluoromethyl group that enhances electron deficiency and metabolic stability, while the cyano and chloro substituents enable direct functionalization in heterocyclic synthesis. This bench-stable building block integrates efficiently into pharmaceutical intermediates and agrochemical scaffolds under standard conditions.

Application

2-Chloro-6-(trifluoromethyl)nicotinonitrile serves as a versatile building block in medicinal chemistry, enabling the construction of bioactive heterocycles via palladium-catalyzed cross-coupling reactions. Its trifluoromethyl and nitrile groups provide strong electron-withdrawing character, enhancing reactivity in nucleophilic substitution and facilitating functionalization at the 2-position. The compound exhibits excellent bench stability and compatibility with standard synthetic protocols, making it ideal for modular synthesis of pharmaceutical intermediates.

Synthesis

  • Route1
    • 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile|CS-0133780
      116548-04-0
    • ~75%
    • In-stock
      2-Chloro-6-(trifluoromethyl)nicotinonitrile|CS-W008691
      386704-06-9

    References

    • US2013/79373 A1, ; Paragraph 0265; 0268 ;
  • Route2
    • 3-Pyridinecarbonitrile, 2-chloro-|CS-0654103
      6602-54-6
    • In-stock
      Zinc(II) Trifluoromethanesulfinate dihydrates|CS-0099251
      39971-65-8
    • ~23%
    • In-stock
      2-Chloro-6-(trifluoromethyl)nicotinonitrile|CS-W008691
      386704-06-9

    References

    • Journal of the American Chemical Society, , vol. 135, # 32 p. 12122 - 12134
  • Route3
    • 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide|CS-0082220
      116548-03-9
    • ~%
    • In-stock
      2-Chloro-6-(trifluoromethyl)nicotinonitrile|CS-W008691
      386704-06-9

    References

    • EP2251329 A1, ; Page/Page column 5 ;

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   36.68
  • LogP   2.62548
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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