6-Bromo-1,2,3,4-tetrahydro-2-quinolinone

Name: 6-Bromo-1,2,3,4-tetrahydro-2-quinolinone
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 3279-90-1
Cat. No. CS-D1588
Purity≥97%
MDL No.MFCD03839832

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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-1,2,3,4-tetrahydro-2-quinolinone|CS-D1588

Structure of 3279-90-1

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General Information

CAS No. 3279-90-1
Cat. No. CS-D1588
Purity ≥97%
MDL No. MFCD03839832
Storage Store at room temperature, keep dry and cool
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₈BrNO
Molecular Weight 226.07
Synonym(s) 6-Bromo-3,4-dihydro-2(1H)-quinolinone; 6-Bromo-1,2,3,4-tetrahydro-2-quinolinone; 6-Bromo-3,4-dihydro-1h-quinolin-2-one
SMILES O=C1NC2=C(C=C(Br)C=C2)CC1

Description

6-Bromo-1,2,3,4-tetrahydro-2-quinolinone features a brominated quinolinone core with enhanced reactivity at the C6 position. This bench-stable heterocycle integrates readily into cross-coupling reactions and serves as a key scaffold for medicinal chemistry libraries. The electron-deficient ring system pairs effectively with palladium catalysts, enabling efficient functionalization under mild conditions.

Application

6-Bromo-1,2,3,4-tetrahydro-2-quinolinone serves as a versatile building block in medicinal chemistry, enabling efficient access to substituted quinoline scaffolds via palladium-catalyzed cross-coupling reactions. Its bromine substituent offers high reactivity in Suzuki, Stille, and Negishi couplings, while the tetrahydroquinolinone core provides a stable, functionalized platform for further derivatization. The compound exhibits excellent bench stability and compatibility with common protecting group strategies, facilitating straightforward purification and integration into multi-step syntheses.

Synthesis

Route1
- In-stock
  
  553-03-7
- ~95%
- In-stock
  
  3279-90-1
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 10, # 14 p. 1559 - 1562
Route2
- In-stock
  
  34598-49-7
- ~0%
- In-stock
  
  147497-32-3
- In-stock
  
  3279-90-1
References
- WO2012/162129 A1, ; Page/Page column 35 ; WO 2012/162129 A1
Route3
- In-stock
  
  34598-49-7
- ~%
- In-stock
  
  3279-90-1
References
- US2004/220206 A1, ; Page 24; 32 ; US 20040220206 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

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Computational Chemistry Data

TPSA 29.1
LogP 2.3338
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Tetrahydroquinoline compounds

Key Words

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6-Bromo-1,2,3,4-tetrahydro-2-quinolinone

CAS No. 3279-90-1

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