4-Chloro-7-hydroxy-6-methoxyquinoline-3-carbonitrile

Name: 4-Chloro-7-hydroxy-6-methoxyquinoline-3-carbonitrile
Brand: ChemScene
Availability: InStock
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CAS No. 263149-10-6
Cat. No. CS-B0215
Molecule weight234.64
Purity≥98%
MDL No.MFCD09833973

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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4-Chloro-7-hydroxy-6-methoxyquinoline-3-carbonitrile|CS-B0215

Structure of 263149-10-6

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General Information

CAS No. 263149-10-6
Cat. No. CS-B0215
Purity ≥98%
MDL No. MFCD09833973
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₇ClN₂O₂
Molecular Weight 234.64
Synonym(s) 4-Chlor-7-hydroxy-6-methoxychinolin-3-carbonitril
SMILES N#CC1=C(Cl)C2=CC(OC)=C(O)C=C2N=C1

Description

4-Chloro-7-hydroxy-6-methoxyquinoline-3-carbonitrile features a polar quinoline core with strategically positioned electron-withdrawing nitrile and chloro groups, enabling robust conjugation and enhanced reactivity in transition metal-catalyzed couplings. The hydroxy and methoxy substituents provide solubility and hydrogen-bonding capacity, supporting its use in medicinal chemistry and fluorescent probe development under standard conditions.

Application

4-Chloro-7-hydroxy-6-methoxyquinoline-3-carbonitrile serves as a versatile heterocyclic building block for medicinal chemistry and materials science applications. Its combination of hydroxyl, methoxy, cyano, and chloro substituents enables selective functionalization via cross-coupling, nucleophilic substitution, and derivatization reactions. The molecule exhibits good bench stability and facilitates efficient purification, making it well-suited for iterative synthesis workflows targeting complex quinoline-based scaffolds.

Synthesis

Route1
- 214476-99-0
- ~99%
- In-stock
  
  263149-10-6
References
- AstraZeneca AB Patent: EP1584619 A1, 2005 ; Location in patent: Page/Page column 41-42 ; EP 1584619 A1
Route2
- 741276-43-7
- ~%
- In-stock
  
  263149-10-6
References
- Cao, Xin; You, Qi-Dong; Li, Zhi-Yu; Liu, Xiao-Rong; Xu, Dan; Guo, Qing-Long; Shang, Jing; Chern, Ji-Wang; Chen, Meng-Ling Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 23 p. 6206 - 6209
Route3
- In-stock
  
  3943-74-6
- ~%
- In-stock
  
  263149-10-6
References
- Wang, Yanong D.; Miller, Karen; Boschelli, Diane H.; Ye, Fei; Wu, Biqi; Floyd; Powell, Dennis W.; Wissner, Allan; Weber, Jennifer M.; Boschelli, Frank Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 21 p. 2477 - 2480

Safety Information

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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 66.14
LogP 2.47408
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Skeleton Aromatic heterocycle compounds quinoline compounds

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4-Chloro-7-hydroxy-6-methoxyquinoline-3-carbonitrile

CAS No. 263149-10-6

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