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

Name: 6-Bromo-4H-imidazo[4,5-b]pyridine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 28279-49-4
Cat. No. CS-W005621
Purity≥97%
MDL No.MFCD00460092

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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6-Bromo-4H-imidazo[4,5-b]pyridine|CS-W005621

Structure of 28279-49-4

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General Information

CAS No. 28279-49-4
Cat. No. CS-W005621
Purity ≥97%
MDL No. MFCD00460092
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄BrN₃
Molecular Weight 198.02
Synonym(s) 6-Bromo-1H-imidazo[4,5-b]pyridine
SMILES C1=C(Br)C=NC2=C1[NH]C=N2

Description

6-Bromo-4H-imidazo[4,5-b]pyridine serves as a versatile heterocyclic scaffold for medicinal chemistry and materials synthesis. The bromine substituent enables direct functionalization via cross-coupling reactions, while the fused imidazopyridine core provides rigidity and electron-deficient character suitable for targeted molecular design. This compound features high thermal stability and compatibility with standard reaction conditions.

Application

6-Bromo-4H-imidazo[4,5-b]pyridine serves as a versatile building block for heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-defined electrophilic bromine site. The imidazopyridine core exhibits robust bench stability and functional group tolerance, facilitating integration into complex scaffolds relevant to medicinal chemistry. Its reactivity profile supports efficient construction of fused polycyclic systems and API intermediates under standard coupling conditions.

Synthesis

Route1
- In-stock
  
  38875-53-5
- 64-18-6
- ~96%
- In-stock
  
  28279-49-4
References
- SCHERING CORPORATION Patent: WO2008/82487 A2, 2008 ; Location in patent: Page/Page column 107 ; WO 2008/082487 A2
Route2
- In-stock
  
  38875-53-5
- 122-51-0
- ~69%
- In-stock
  
  28279-49-4
References
- Macdonald, Jonathan; Oldfield, Victoria; Bavetsias, Vassilios; Blagg, Julian Organic and Biomolecular Chemistry, 2013 , vol. 11, # 14 p. 2335 - 2347
Route3
- In-stock
  
  38875-53-5
- 149-73-5
- ~87%
- In-stock
  
  28279-49-4
References
- Burger, Matthew T.; Knapp, Mark; Wagman, Allan; Ni, Zhi-Jie; Hendrickson, Thomas; Atallah, Gordana; Zhang, Yanchen; Frazier, Kelly; Verhagen, Joelle; Pfister, Keith; Ng, Simon; Smith, Aaron; Bartulis, Sarah; Merrit, Hanne; Weismann, Marion; Xin, Xiaohua; Haznedar, Joshua; Voliva, Charles F.; Iwanowicz, Ed; Pecchi, Sabina ACS Medicinal Chemistry Letters, 2011 , vol. 2, # 1 p. 34 - 38

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 1.7204
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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6-Bromo-4H-imidazo[4,5-b]pyridine

CAS No. 28279-49-4

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