6-Bromo-4-hydroxyquinolin-2(1H)-one

Name: 6-Bromo-4-hydroxyquinolin-2(1H)-one
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 54675-23-9
Cat. No. CS-0041628
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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6-Bromo-4-hydroxyquinolin-2(1H)-one|CS-0041628

Structure of 54675-23-9

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General Information

CAS No. 54675-23-9
Cat. No. CS-0041628
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₆BrNO₂
Molecular Weight 240.05
Synonym(s) 6-bromo-4-hydroxy-1H-quinolin-2-one
SMILES O=C1NC2=C(C=C(Br)C=C2)C(O)=C1

Description

6-Bromo-4-hydroxyquinolin-2(1H)-one features a brominated quinolinone core with a strategically positioned hydroxyl group, enabling direct functionalization in cross-coupling and derivatization workflows. The electron-deficient framework supports efficient transition metal catalysis, while the bench-stable structure facilitates handling under standard conditions.

Application

6-Bromo-4-hydroxyquinolin-2(1H)-one serves as a versatile building block for the synthesis of substituted quinolones, enabling direct functionalization at the C6 position via palladium-catalyzed cross-coupling reactions. The hydroxyl group provides a handle for derivatization or protection, while the bromine substituent offers high reactivity in Suzuki, Stille, and Negishi coupling protocols. Its bench-stable crystalline form facilitates handling and purification, making it well-suited for medicinal chemistry campaigns and API intermediate development.

Synthesis

Route1
- 95262-09-2
- ~99%
- In-stock
  
  54675-23-9
References
- BRISTOL-MYERS SQUIBB COMPANY Patent: WO2007/70818 A1, 2007 ; Location in patent: Page/Page column 101-102 ; WO 2007/070818 A1
Route2
- 106-40-1
- ~%
- In-stock
  
  54675-23-9
References
- Synthetic Communications, , vol. 40, # 5 p. 732 - 738
Route3
- 79612-79-6
- ~%
- In-stock
  
  54675-23-9
References
- WO2013/74386 A2, ;

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 53.09
LogP 1.9962
H_Acceptors 2
H_Donors 2
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-hydroxyquinolin-2(1H)-one

CAS No. 54675-23-9

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