6-Bromo-2-chloro-3H-imidazo[4,5-b]pyridine

Name: 6-Bromo-2-chloro-3H-imidazo[4,5-b]pyridine
Brand: ChemScene
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CAS No. 438190-89-7
Cat. No. CS-0133599
Purity≥96%
MDL No.None

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6-Bromo-2-chloro-3H-imidazo[4,5-b]pyridine|CS-0133599

Structure of 438190-89-7

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General Information

CAS No. 438190-89-7
Cat. No. CS-0133599
Purity ≥96%
MDL No. None
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₃BrClN₃
Molecular Weight 232.47
Synonym(s) 5-Bromo-2-chloro-7-azabenzimidazole
SMILES ClC1=NC2=CC(Br)=CN=C2N1

Description

6-Bromo-2-chloro-3H-imidazo[4,5-b]pyridine is a heterocyclic scaffold featuring bromo and chloro substituents at strategic positions, enabling direct functionalization in cross-coupling reactions. This electron-deficient imidazopyridine serves as a key intermediate for constructing bioactive molecules in medicinal chemistry and agrochemical development.

Application

6-Bromo-2-chloro-3H-imidazo[4,5-b]pyridine serves as a versatile heterocyclic building block for medicinal chemistry and catalytic cross-coupling applications. The molecule’s dual halogenation pattern enables sequential functionalization via Pd-catalyzed coupling reactions, with the bromo group typically exhibiting higher reactivity than the chloro substituent. Its stability under standard reaction conditions and compatibility with diverse functional groups make it well-suited for constructing complex pharmaceutical scaffolds and kinase inhibitor cores in high-throughput synthesis workflows.

Synthesis

Route1
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References
- NEUROGEN CORPORATION Patent: US2003/36652 A1, 2003 ; US 20030036652 A1

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 41.57
LogP 2.3738
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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6-Bromo-2-chloro-3H-imidazo[4,5-b]pyridine

CAS No. 438190-89-7

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