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Ethyl 2-chloro-3-cyano-6-(trifluoromethyl)-pyridine-5-carboxylate

  • CAS No. 175277-73-3

  • Cat. No. CS-0061543
  • Purity≥98%
  • MDL No.None

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

Ethyl 2-chloro-3-cyano-6-(trifluoromethyl)-pyridine-5-carboxylate|CS-0061543

Structure of 175277-73-3

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General Information

  • CAS No. 175277-73-3
  • Cat. No. CS-0061543
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₆ClF₃N₂O₂
  • Molecular Weight 278.62
  • Synonym(s) Ethyl 6-chloro-5-cyano-2-(trifluoromethyl)nicotinate
  • SMILES CCOC(=O)C1=C(C(F)(F)F)N=C(C(=C1)C#N)Cl

Description

Ethyl 2-chloro-3-cyano-6-(trifluoromethyl)pyridine-5-carboxylate features a trifluoromethyl group that enhances electron deficiency and metabolic stability. The cyano and ester functionalities enable efficient coupling reactions, while the chloro substituent facilitates palladium-catalyzed cross-coupling. This compound serves as a key intermediate in synthesizing bioactive heterocycles for pharmaceutical development under standard conditions.

Application

Ethyl 2-chloro-3-cyano-6-(trifluoromethyl)pyridine-5-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to complex pyridine-based scaffolds. The molecule combines orthogonal functional groups—chloro, cyano, trifluoromethyl, and ester—that facilitate sequential transformations via cross-coupling, nucleophilic substitution, and cyclization reactions. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • Ethyl 5-cyano-6-hydroxy-2-(trifluoromethyl)pyridine-3-carboxylate|CS-0260562
      144456-86-0
    • ~92%
    • In-stock
      Ethyl 2-chloro-3-cyano-6-(trifluoromethyl)-pyridine-5-carboxylate|CS-0061543
      175277-73-3

    References

    • ASTRAZENECA AB Patent: WO2008/4943 A1, 2008 ; Location in patent: Page/Page column 54-55 ; WO 2008/004943 A1
  • Route2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 21, # 10 p. 2877 - 2881
  • Route3
    • null|null
      372-31-6
    • ~%
    • In-stock
      Ethyl 2-chloro-3-cyano-6-(trifluoromethyl)-pyridine-5-carboxylate|CS-0061543
      175277-73-3

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 21, # 10 p. 2877 - 2881

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-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   62.98
  • LogP   2.80218
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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