4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Name: 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 958230-19-8
Cat. No. CS-B0563
Purity≥97%
MDL No.MFCD09859124

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4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde|CS-B0563

Structure of 958230-19-8

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General Information

CAS No. 958230-19-8
Cat. No. CS-B0563
Purity ≥97%
MDL No. MFCD09859124
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₅ClN₂O
Molecular Weight 180.59
Synonym(s) 4-Chlor-1H-pyrrolo[2,3-b]pyridin-5-carbaldehyd
SMILES O=CC1=CN=C(NC=C2)C2=C1Cl

Description

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde features a rigid heteroaromatic core with a chlorinated pyrrolopyridine scaffold and a formyl group at the 5-position. This electron-deficient aldehyde integrates readily into cross-coupling reactions and serves as a key building block for bioactive molecules in medicinal chemistry and materials science.

Application

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde serves as a versatile building block in medicinal chemistry, enabling direct incorporation of both chlorinated heterocyclic and aldehyde functionalities into target molecules. The aldehyde group facilitates nucleophilic additions, reductive aminations, and condensation reactions, while the pyrrolopyridine core provides a rigid, electron-deficient scaffold suitable for bioactive compound design. Bench-stable and compatible with standard purification techniques, it functions efficiently in multistep syntheses requiring orthogonal reactivity.

Synthesis

Route1
- 68-12-2
- In-stock
  
  651744-48-8
- ~89%
- In-stock
  
  958230-19-8
References
- ABBOTT LABORATORIES; WISHART, Neil; ARGIRIADI, Maria A.; BREINLINGER, Eric C.; CALDERWOOD, David J.; ERICSSON, Anna M.; FIAMENGO, Bryan A.; FRANK, Kristine E.; FRIEDMAN, Michael; GEORGE, Dawn M.; GOEDKEN, Eric R.; JOSEPHSOHN, Nathan S.; LI, Biqin C.; MORYTKO, Michael J.; MULLEN, Kelly D.; SOMAL, Gagandeep; STEWART, Kent D.; VOSS, Jeffrey W.; WALLACE, Grier A.; WANG, Lu; WOLLER, Kevin R. Patent: WO2011/68899 A1, 2011 ; Location in patent: Page/Page column 126-127 ; WO 2011/068899 A1
Route2
- 68-12-2
- In-stock
  
  651744-48-8
- ~%
- In-stock
  
  958230-19-8
- 924655-39-0
References
- WO2006/124731 A2, ; Page/Page column 25-26 ; WO 2006/124731 A2
Route3
- In-stock
  
  55052-28-3
- ~%
- In-stock
  
  958230-19-8
References
- WO2011/68899 A1, ; WO 2011/068899 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-H319
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 45.75
LogP 2.0288
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Key Words

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4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

CAS No. 958230-19-8

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