2-Chloro-7-nitroquinoline

Name: 2-Chloro-7-nitroquinoline
Brand: ChemScene
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CAS No. 49609-03-2
Cat. No. CS-0156840
Purity≥97%
MDL No.None

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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+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 49609-03-2

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General Information

CAS No. 49609-03-2
Cat. No. CS-0156840
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₅ClN₂O₂
Molecular Weight 208.60
Synonym(s) Quinoline,2-chloro-7-nitro
SMILES C1=CC(=CC2=NC(=CC=C12)Cl)[N+](=O)[O-]

Description

2-Chloro-7-nitroquinoline is a fluorophore-bearing heterocycle featuring a chlorine atom at the 2-position and a nitro group at the 7-position. This electron-deficient scaffold enables efficient coupling in C–H functionalization and transition metal-catalyzed cross-coupling reactions. The molecule exhibits strong fluorescence with high quantum yield, making it valuable for probe design and bioimaging applications.

Application

2-Chloro-7-nitroquinoline serves as a versatile building block in medicinal chemistry, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. Its electron-deficient quinoline core exhibits enhanced reactivity toward nucleophilic substitution, facilitating the synthesis of diverse heterocyclic scaffolds. The orthogonal presence of chloro and nitro groups allows for sequential transformations under mild conditions, supporting modular drug discovery workflows. Bench-stable and readily purified, it functions effectively in both small-molecule library synthesis and process-scale applications.

Synthesis

Route1
- In-stock
  
  75755-37-2
- ~92%
- In-stock
  
  49609-03-2
References
- Nasr; Drach; Smith; Shipman Jr.; Burckhalter Journal of Medicinal Chemistry, 1988 , vol. 31, # 7 p. 1347 - 1351
Route2
- In-stock
  
  613-51-4
- ~%
- In-stock
  
  49609-03-2
References
- Cidda, Claudio; Sleiter, Giancarlo Gazzetta Chimica Italiana, 1980 , vol. 110, # 2/3 p. 155 - 162
Route3
- 99-09-2
- ~%
- In-stock
  
  49609-03-2
References
- Cidda, Claudio; Sleiter, Giancarlo Gazzetta Chimica Italiana, 1980 , vol. 110, # 2/3 p. 155 - 162

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-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 56.03
LogP 2.7964
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic heterocycle compounds quinoline compounds

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2-Chloro-7-nitroquinoline

CAS No. 49609-03-2

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