6-BROMO-2(1H)-QUINOLONE Chemical Properties

Melting point:

278-280?C

Boiling point:

393.8±42.0 °C(Predicted)

Density 

1.620±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO

form 

Solid

pka

10.76±0.70(Predicted)

color 

Beige

InChI

InChI=1S/C9H6BrNO/c10-7-2-3-8-6(5-7)1-4-9(12)11-8/h1-5H,(H,11,12)

InChIKey

YLAFBGATSQRSTB-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(Br)C=C2)C=CC1=O

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

3

HS Code 

2933499090

6-BROMO-2(1H)-QUINOLONE Usage And Synthesis

Chemical Properties

Beige Solid

Uses

6-Bromo-2(1H)-quinolinone is a useful intermediate for the synthesis of other quinoline derivatives.

Synthesis

General procedure for the synthesis of 6-bromoquinolin-2(1H)-one from the compound (CAS:327058-51-5): 6-bromo-2(1H)-quinolinone (6.0 g, 22.2 mmol) was dissolved in concentrated H2SO4 (30 mL) and the reaction was heated in an oil bath at 100 °C overnight. Upon completion of the reaction, the mixture was cooled to room temperature and quenched with ice water. The precipitate precipitated was collected by filtration, washed with water and subsequently dried under vacuum to afford 6-bromoquinolin-2(1H)-one as a white solid (4.8 g, 97% yield). Mass spectrum (ES+) m/e 225 [M+H]+.

References

[1] Patent: WO2006/132739, 2006, A2. Location in patent: Page/Page column 35-36
[2] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 508 - 518
[3] European Journal of Medicinal Chemistry, 2000, vol. 35, # 10, p. 931 - 940
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 306 - 311

6-BROMO-2(1H)-QUINOLONE(1810-66-8)Related Product Information

• 6-Bromoquinoxaline
• 6-bromoquinoxalin-2(1H)-one
• 6-BROMO-QUINAZOLIN-4-YLAMINE
• 6-bromoquinoxalin-2-amine
• 6-BroMoquinolin-3-aMine
• 3-Quinolinecarboxaldehyde, 6-broMo-
• 6-BroMoquinoline-3-carbonitrile
• 6-BROMOQUINOLINE-3-CARBOXYLIC ACID
• 6-Bromoquinazoline
• 6-BroMoquinoline-2-carbaldehyde
• 6-Bromoquinoline
• 6-Bromo-4-hydroxyquinoline
• 6-BROMO-2-HYDROXYQUINOLINE-4-CARBOXYLIC ACID
• 6-bromo-3-methyl-3H-dibenz[f,ij]isoquinoline-2,7-dione
• 6-BROMO-4-METHYLQUINOLIN-2(1H)-ONE
• 6-BROMO-2(1H)-QUINOLONE
• ETHYL 6,8-DIBROMO-2-OXO-1,2-DIHYDRO-3-QUINOLINECARBOXYLATE
• 6-BROMO-3-ETHYL-2-METHOXYQUINOLINE