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2-Chloro-6-iodoquinoline

  • CAS No. 124467-20-5

  • Cat. No. CS-0132179
  • Purity≥97%
  • MDL No.MFCD04115269

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

2-Chloro-6-iodoquinoline|CS-0132179

Structure of 124467-20-5

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General Information

  • CAS No. 124467-20-5
  • Cat. No. CS-0132179
  • Purity ≥97%
  • MDL No. MFCD04115269
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅ClIN
  • Molecular Weight 289.50
  • Synonym(s) Quinoline, 2-chloro-6-iodo-
  • SMILES IC1=CC=C2N=C(Cl)C=CC2=C1

Description

2-Chloro-6-iodoquinoline is a halogenated quinoline scaffold featuring complementary reactive sites for cross-coupling. The chlorine and iodine substituents enable sequential functionalization, with the iodine group favoring palladium-catalyzed reactions under mild conditions. This compound serves as a strategic intermediate in the synthesis of bioactive heterocycles and advanced pharmaceutical candidates.

Application

2-Chloro-6-iodoquinoline serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient access to substituted quinoline scaffolds. The orthogonal halogen reactivity—chlorine at C2 and iodine at C6—facilitates sequential functionalization under mild conditions. Its bench-stable nature and compatibility with Pd- and Ni-catalyzed couplings make it ideal for constructing complex heterocyclic architectures in medicinal chemistry and materials science workflows.

Synthesis

  • Route1

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 10, # 14 p. 1559 - 1562
  • Route2

    References

    • Chen, Li; Chen, Shaoqing; Michoud, Christophe Patent: US2006/63804 A1, 2006 ; Location in patent: Page/Page column 9-10 ; US 20060063804 A1
  • Route3

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 10, # 14 p. 1559 - 1562

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   12.89
  • LogP   3.4928
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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