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

Name: 4-Chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine
Brand: ChemScene
Availability: InStock
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CAS No. 918519-53-6
Cat. No. CS-B0492
Purity≥98%
MDL No.MFCD09880131

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4-Chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine|CS-B0492

Structure of 918519-53-6

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General Information

CAS No. 918519-53-6
Cat. No. CS-B0492
Purity ≥98%
MDL No. MFCD09880131
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄ClN₃O₂
Molecular Weight 197.58
Synonym(s) 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-3-nitro-
SMILES ClC1=C2C([N+]([O-])=O)=CNC2=NC=C1

Description

4-Chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine is a heterocyclic scaffold featuring a chlorine atom at the 4-position and a nitro group at the 3-position, conferring high electrophilicity and enabling selective coupling reactions. This bench-stable, moisture-tolerant building block integrates readily into complex molecular architectures through palladium-catalyzed transformations and serves as a key intermediate in medicinal chemistry and materials science applications.

Application

4-Chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C4 position via palladium-catalyzed cross-coupling reactions. The nitro group facilitates subsequent reduction and derivatization, while the pyrrolo[2,3-b]pyridine core provides a rigid, planar scaffold with favorable electronic properties for targeted drug discovery applications.

Synthesis

Route1
- In-stock
  
  55052-28-3
- ~93%
- In-stock
  
  918519-53-6
References
- GENENTECH, INC.; HAN, Chong Patent: WO2013/163109 A1, 2013 ; Location in patent: Paragraph 00118 ;
Route2
- 74420-07-8
- 74420-06-7
- ~%
- In-stock
  
  918519-53-6
References
- WO2007/7919 A2, ; Page/Page column 43-44 ; WO 2007/007919 A2

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301-H311-H331
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361+P364-P405-P501

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Computational Chemistry Data

TPSA 71.82
LogP 2.1245
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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

CAS No. 918519-53-6

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