5,7-Dichloro-3H-imidazo[4,5-b]pyridine

Name: 5,7-Dichloro-3H-imidazo[4,5-b]pyridine
Brand: ChemScene
Availability: InStock
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CAS No. 24485-01-6
Cat. No. CS-W005069
Purity≥98%
MDL No.MFCD11111407

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5,7-Dichloro-3H-imidazo[4,5-b]pyridine|CS-W005069

Structure of 24485-01-6

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General Information

CAS No. 24485-01-6
Cat. No. CS-W005069
Purity ≥98%
MDL No. MFCD11111407
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₃Cl₂N₃
Molecular Weight 188.01
Synonym(s) 5,7-dichloro-7aH-imidazo[4,5-b]pyridine
SMILES ClC1=C2C(N=CN2)=NC(Cl)=C1

Description

5,7-Dichloro-3H-imidazo[4,5-b]pyridine is a heterocyclic scaffold featuring two chlorine substituents at electron-rich positions, enhancing its utility in medicinal chemistry. This bench-stable, moisture-tolerant core integrates readily into kinase inhibitors and bioactive scaffolds, offering improved binding affinity through strategic halogen bonding interactions.

Application

5,7-Dichloro-3H-imidazo[4,5-b]pyridine serves as a versatile heterocyclic building block in medicinal chemistry, enabling the synthesis of kinase inhibitors and other bioactive scaffolds. Its dichloro substitution pattern facilitates efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. The compound exhibits good bench stability, moderate solubility in common organic solvents, and compatibility with standard protecting group strategies, making it well-suited for iterative synthesis workflows in drug discovery programs.

Synthesis

Route1
- 14432-11-2
- ~91%
- In-stock
  
  24485-01-6
References
- GLAXOSMITHKLINE LLC; RIVERO, Ralph, A.; TEDESCO, Rosanna Patent: WO2013/95761 A1, 2013 ; Location in patent: Page/Page column 32; 33; 34 ;
Route2
- 6863-46-3
- ~%
- In-stock
  
  24485-01-6
References
- Journal of Medicinal Chemistry, , vol. 50, # 4 p. 828 - 834
Route3
- In-stock
  
  273-21-2
- ~%
- In-stock
  
  24485-01-6
References
- Journal of Medicinal Chemistry, , vol. 50, # 4 p. 828 - 834

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 41.57
LogP 2.2647
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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5,7-Dichloro-3H-imidazo[4,5-b]pyridine

CAS No. 24485-01-6

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