2-Oxo-1,2-dihydroquinoline-6-sulfonyl chloride

Name: 2-Oxo-1,2-dihydroquinoline-6-sulfonyl chloride
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 569340-07-4
Cat. No. CS-0080680
Purity≥97%
MDL No.MFCD18300284

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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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2-Oxo-1,2-dihydroquinoline-6-sulfonyl chloride|CS-0080680

Structure of 569340-07-4

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General Information

CAS No. 569340-07-4
Cat. No. CS-0080680
Purity ≥97%
MDL No. MFCD18300284
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₆ClNO₃S
Molecular Weight 243.67
Synonym(s) 2-Hydroxyquinoline-6-sulfonyl chloride
SMILES O=S(C1=CC2=C(NC(C=C2)=O)C=C1)(Cl)=O

Description

2-Oxo-1,2-dihydroquinoline-6-sulfonyl chloride features a fused quinoline core with a reactive sulfonyl chloride group at the 6-position, enabling direct coupling in amide bond formation. The electron-deficient aromatic system enhances electrophilicity, while the keto functionality offers potential for further derivatization. This compound serves as a robust scaffold for synthesizing bioactive molecules and functional materials under standard conditions.

Application

2-Oxo-1,2-dihydroquinoline-6-sulfonyl chloride serves as a versatile acylating agent for constructing sulfonamide-linked heterocyclic scaffolds. Its reactivity enables efficient coupling with amines under mild conditions, facilitating the synthesis of biologically relevant quinoline-based derivatives. The molecule exhibits bench stability and facilitates straightforward purification, making it well-suited for iterative medicinal chemistry campaigns and API intermediate development.

Synthesis

Route1
- In-stock
  
  59-31-4
- ~59%
- In-stock
  
  569340-07-4
References
- PRESIDENT AND FELLOWS OF HARVARD COLLEGE; WALKER, Suzanne, Kahne; LAZARUS, Michael, Block; GROSS, Benjamin, J. Patent: WO2010/141074 A2, 2010 ; Location in patent: Page/Page column 50 ; WO 2010/141074 A2
Route2
- 7790-94-5
- In-stock
  
  59-31-4
- ~68%
- In-stock
  
  569340-07-4
References
- Tashima, Toshihiko; Murata, Hiroaki; Kodama, Hidehiko Bioorganic and Medicinal Chemistry, 2014 , vol. 22, # 14 p. 3720 - 3731

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05,GHS07
Signal Word : Danger	UN#: 1759
Class : 8	Packing Group : Ⅲ
Hazard Statements : H302-H314
Precautionary Statements : P260-P264-P270-P280-P301+P330+P331-P304+P340-P330-P363-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 67
LogP 1.4556
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds quinoline compounds

Key Words

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2-Oxo-1,2-dihydroquinoline-6-sulfonyl chloride

CAS No. 569340-07-4

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