3-Bromo-4-nitro-1H-pyrrolo[2,3-b]pyridine

Name: 3-Bromo-4-nitro-1H-pyrrolo[2,3-b]pyridine
Brand: ChemScene
Availability: InStock
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CAS No. 869335-36-4
Cat. No. CS-0002362
Molecule weight242.03
Purity≥98%
MDL No.MFCD09880133

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3-Bromo-4-nitro-1H-pyrrolo[2,3-b]pyridine|CS-0002362

Structure of 869335-36-4

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General Information

CAS No. 869335-36-4
Cat. No. CS-0002362
Purity ≥98%
MDL No. MFCD09880133
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄BrN₃O₂
Molecular Weight 242.03
Synonym(s) 3-BroMo-4-nitro-7-azaindole
SMILES O=[N+](C1=C2C(NC=C2Br)=NC=C1)[O-]

Description

3-Bromo-4-nitro-1H-pyrrolo[2,3-b]pyridine is a heteroaromatic building block featuring a bromine at the 3-position and a nitro group at the 4-position on a pyrrolo[2,3-b]pyridine core. This electron-deficient scaffold enables efficient cross-coupling reactions and serves as a key intermediate in the synthesis of functionalized polycyclic systems for medicinal chemistry and materials applications.

Application

3-Bromo-4-nitro-1H-pyrrolo[2,3-b]pyridine serves as a versatile building block for the synthesis of bioactive heterocycles, enabling palladium-catalyzed cross-coupling reactions due to its bromine functionality. The nitro group enhances electrophilicity at C4 and supports subsequent reduction and functionalization sequences. Its bench-stable nature and compatibility with standard synthetic workflows make it well-suited for medicinal chemistry and process development applications.

Synthesis

Route1
- 83683-82-3
- ~%
- In-stock
  
  869335-36-4
References
- Bayer HealthCare AG Patent: US2008/269268 A1, 2008 ;
Route2
- 74420-06-7
- ~31%
- In-stock
  
  869335-36-4
References
- BAYER HEALTHCARE AG Patent: WO2005/108397 A1, 2005 ; Location in patent: Page/Page column 43-44 ;

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 71.82
LogP 2.2336
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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3-Bromo-4-nitro-1H-pyrrolo[2,3-b]pyridine

CAS No. 869335-36-4

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