6-Bromo-4-iodoquinoline

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

CAS No. 927801-23-8
Cat. No. CS-M0127
Purity≥97%
MDL No.MFCD08437008

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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 927801-23-8

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General Information

CAS No. 927801-23-8
Cat. No. CS-M0127
Purity ≥97%
MDL No. MFCD08437008
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₅BrIN
Molecular Weight 333.95
Synonym(s) T66 BNJ EI HE
SMILES IC1=CC=NC2=C1C=C(Br)C=C2

Description

6-Bromo-4-iodoquinoline is a dual-halogenated quinoline scaffold enabling efficient cross-coupling transformations in medicinal chemistry. The strategically positioned bromo and iodo groups facilitate sequential Pd-catalyzed reactions, allowing rapid diversification at distinct ring positions. This ortho-selective halogen arrangement supports modular synthesis of complex heterocyclic architectures under standard conditions.

Application

6-Bromo-4-iodoquinoline serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling the construction of biaryl and heteroaryl scaffolds. The orthogonal reactivity of bromo and iodo substituents facilitates sequential functionalization under standard Pd-catalyzed conditions. Its bench-stable nature and compatibility with diverse reaction partners make it well-suited for medicinal chemistry and process development workflows.

Synthesis

Route1
- 1086062-75-0
- ~91%
- In-stock
  
  927801-23-8
References
- Wang, Min; Gao, Mingzhang; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 4 p. 1569 - 1574
Route2
- In-stock
  
  65340-70-7
- ~98%
- In-stock
  
  927801-23-8
References
- Knight, Steven D.; Adams, Nicholas D.; Burgess, Joelle L.; Chaudhari, Amita M.; Darcy, Michael G.; Donatelli, Carla A.; Luengo, Juan I.; Newlander, Ken A.; Parrish, Cynthia A.; Ridgers, Lance H.; Sarpong, Martha A.; Schmidt, Stanley J.; Van Aller, Glenn S.; Carson, Jeffrey D.; Diamond, Melody A.; Elkins, Patricia A.; Gardiner, Christine M.; Garver, Eric; Gilbert, Seth A.; Gontarek, Richard R.; Jackson, Jeffrey R.; Kershner, Kevin L.; Luo, Lusong; Raha, Kaushik; Sherk, Christian S.; Sung, Chiu-Mei; Sutton, David; Tummino, Peter J.; Wegrzyn, Ronald J.; Auger, Kurt R.; Dhanak, Dashyant ACS Medicinal Chemistry Letters, 2010 , vol. 1, # 1 p. 39 - 43
Route3
- In-stock
  
  187278-01-9
- ~%
- In-stock
  
  927801-23-8
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 4 p. 1569 - 1574

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 12.89
LogP 3.6019
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds quinoline compounds

Key Words

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6-Bromo-4-iodoquinoline

CAS No. 927801-23-8

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