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2-Chloro-3-(trifluoromethyl)quinoxaline

  • CAS No. 254732-51-9

  • Cat. No. CS-0155914
  • Purity≥98%
  • MDL No.MFCD00243891

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

2-Chloro-3-(trifluoromethyl)quinoxaline|CS-0155914

Structure of 254732-51-9

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General Information

  • CAS No. 254732-51-9
  • Cat. No. CS-0155914
  • Purity ≥98%
  • MDL No. MFCD00243891
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₄ClF₃N₂
  • Molecular Weight 232.59
  • Synonym(s) ST5407629
  • SMILES C1=CC=C2C(=C1)N=C(C(=N2)Cl)C(F)(F)F

Description

2-Chloro-3-(trifluoromethyl)quinoxaline is a bench-stable heterocyclic building block featuring a chlorine atom at the 2-position and a trifluoromethyl group at the 3-position, enabling selective cross-coupling reactions. This electron-deficient quinoxaline integrates efficiently into pharmaceutical scaffolds and functional materials, offering enhanced metabolic stability and tunable electronic properties through its fluorinated substituent.

Application

2-Chloro-3-(trifluoromethyl)quinoxaline serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its electrophilic chlorine and electron-deficient quinoxaline core. The trifluoromethyl group enhances metabolic stability and lipophilicity, while the compound exhibits bench stability and compatibility with standard reaction conditions. It functions effectively in Suzuki-Miyaura, Stille, and Buchwald-Hartwig couplings, facilitating rapid access to diverse heterocyclic scaffolds for API development.

Synthesis

  • Route1

    References

    • US2010/120778 A1, ; Page/Page column 24 ;

Safety Information

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GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   25.78
  • LogP   3.302
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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