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CS-W001157 4
Total: USD 88.00

2-Chloro-6-fluoroquinoxaline

  • CAS No. 55687-33-7

  • Cat. No. CS-0019227
  • Purity≥95%
  • MDL No.MFCD09999192

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

2-Chloro-6-fluoroquinoxaline|CS-0019227

Structure of 55687-33-7

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General Information

  • CAS No. 55687-33-7
  • Cat. No. CS-0019227
  • Purity ≥95%
  • MDL No. MFCD09999192
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄ClFN₂
  • Molecular Weight None
  • Synonym(s) None
  • SMILES FC1=CC=C2N=C(Cl)C=NC2=C1

Description

2-Chloro-6-fluoroquinoxaline is a heterocyclic electrophile featuring orthogonal halogen handles enabling sequential cross-coupling. The electron-deficient core pairs with nucleophiles under palladium catalysis, while the fluorine atom facilitates further functionalization via nucleophilic aromatic substitution. This dual-reactive scaffold supports modular synthesis in medicinal chemistry and materials science.

Application

2-Chloro-6-fluoroquinoxaline serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its complementary halogen reactivity. The ortho-chloro and meta-fluoro substituents provide orthogonal functionalization potential, facilitating sequential derivatization. Its stability under standard reaction conditions and compatibility with diverse nucleophiles make it well-suited for constructing complex heterocyclic scaffolds in API development.

Synthesis

  • Route1
    • 7-Fluoroquinoxalin-2(1H)-one|CS-0723010
      145323-53-1
    • In-stock
      6-Fluoroquinoxalin-2(1H)-one|CS-0187216
      55687-23-5
    • ~0%
    • 2-Chloro-7-fluoroquinoxaline|CS-0214730
      1233932-59-6
    • In-stock
      2-Chloro-6-fluoroquinoxaline|CS-0019227
      55687-33-7

    References

    • Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael Patent: US2013/115190 A1, 2013 ; Location in patent: Page/Page column ;
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 24, # 1 p. 93 - 101
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 24, # 1 p. 93 - 101

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   25.78
  • LogP   2.4223
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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