6-Bromo-4-chloro-3-nitroquinoline

Name: 6-Bromo-4-chloro-3-nitroquinoline
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 723281-72-9
Cat. No. CS-B0353
Purity≥95%
MDL No.MFCD09909913

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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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6-Bromo-4-chloro-3-nitroquinoline|CS-B0353

Structure of 723281-72-9

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General Information

CAS No. 723281-72-9
Cat. No. CS-B0353
Purity ≥95%
MDL No. MFCD09909913
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₄BrClN₂O₂
Molecular Weight 287.50
Synonym(s) quinoline, 6-bromo-4-chloro-3-nitro-
SMILES ClC1=C([N+]([O-])=O)C=NC2=CC=C(Br)C=C21

Description

6-Bromo-4-chloro-3-nitroquinoline features a highly functionalized quinoline core with bromo, chloro, and nitro groups positioned for orthogonal reactivity. This electron-deficient scaffold enables efficient coupling in cross-coupling reactions and serves as a key intermediate in the synthesis of bioactive heterocycles and advanced pharmaceutical candidates.

Application

6-Bromo-4-chloro-3-nitroquinoline serves as a versatile building block for the synthesis of functionalized quinoline scaffolds. Its strategic placement of bromo, chloro, and nitro groups enables sequential cross-coupling reactions and selective reductions, facilitating access to complex heterocyclic architectures. The molecule exhibits good bench stability and compatibility with standard palladium-catalyzed transformations, making it well-suited for medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  853908-50-6
- ~91%
- In-stock
  
  723281-72-9
References
- PROGENICS PHARMACEUTICALS, INC. Patent: WO2009/155527 A2, 2009 ; Location in patent: Page/Page column 142 ; WO 2009/155527 A2
Route2
- 853908-49-3
- ~%
- In-stock
  
  723281-72-9
References
- WO2012/7926 A1, ; WO 2012/007926 A1 US2012/108627 A1, ; WO2012/77031 A1, ; WO 2012/077031 A1
Route3
- 1201643-75-5
- ~%
- In-stock
  
  723281-72-9
References
- WO2011/1212 A1, ; WO 2011/001212 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-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 56.03
LogP 3.5589
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds quinoline compounds

Key Words

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6-Bromo-4-chloro-3-nitroquinoline

CAS No. 723281-72-9

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