8-Chloroquinoline-2-carbaldehyde

Name: 8-Chloroquinoline-2-carbaldehyde
Brand: ChemScene
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CAS No. 59394-28-4
Cat. No. CS-0157008
Molecule weight191.61
Purity≥95%
MDL No.MFCD06407641

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
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8-Chloroquinoline-2-carbaldehyde|CS-0157008

Structure of 59394-28-4

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General Information

CAS No. 59394-28-4
Cat. No. CS-0157008
Purity ≥95%
MDL No. MFCD06407641
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₆ClNO
Molecular Weight 191.61
Synonym(s) 8-CHLORO-QUINOLINE-2-CARBALDEHYDE
SMILES C1=CC(=C2C(=C1)C=CC(=N2)C=O)Cl

Description

8-Chloroquinoline-2-carbaldehyde features a chlorinated quinoline core with an aldehyde functional group at the 2-position, enabling direct coupling in heterocyclic synthesis. This electron-deficient scaffold integrates readily into bioactive molecule frameworks, particularly in medicinal chemistry and ligand design. The compound exhibits enhanced reactivity due to the combined influence of the electron-withdrawing chlorine and carbonyl groups.

Application

8-Chloroquinoline-2-carbaldehyde serves as a versatile building block in medicinal chemistry, enabling the construction of quinoline-based scaffolds through standard coupling and functionalization reactions. Its electrophilic aldehyde group facilitates efficient imine formation and reductive amination, while the chlorine substituent supports palladium-catalyzed cross-coupling. The compound exhibits good bench stability and is compatible with common purification methods, making it well-suited for iterative synthesis campaigns in API development.

Synthesis

Route1
- In-stock
  
  3033-82-7
- ~97%
- In-stock
  
  59394-28-4
References
- Barbier, Christine; Joissains, Arnaud; Commercon, Alain; Riou, Jean-Francois; Huet, Francois Heterocycles, 2000 , vol. 53, # 1 p. 37 - 48
Route2
- 1165569-14-1
- ~74%
- In-stock
  
  59394-28-4
References
- Ballesteros-Garrido, Rafael; Leroux, Frederic R.; Ballesteros, Rafael; Abarca, Belen; Colobert, Francoise Tetrahedron, 2009 , vol. 65, # 22 p. 4410 - 4417

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 : P264-P270-P280-P330-P501

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Computational Chemistry Data

TPSA 29.96
LogP 2.7007
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic heterocycle compounds quinoline compounds

Key Words

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8-Chloroquinoline-2-carbaldehyde

CAS No. 59394-28-4

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