8-bromo-5-fluoroquinoline Chemical Properties

Boiling point:

294.2±20.0 °C(Predicted)

Density 

1.647±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

1.35±0.29(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

2933491090

8-bromo-5-fluoroquinoline Usage And Synthesis

Uses

8-Bromo-5-fluoroquinoline is used as a novel binder in the synthesis of 5HT1A, and also acts as a receptor antagonist and agonist. This drug has excellent efficacy for central nervous system disorders, such as cognitive impairment, anxiety disorders, depression, and sexual dysfunction.

Synthesis

2-Bromo-5-fluoroaniline (100 g, 1.0 eq.), 4-nitrophenol (40 g, 0.54 eq.) and glycerol (97 g, 2.0 eq.) were slowly added to pre-mixed sulfuric acid (267 mL) and water (114 mL) at 140-150 °C and the reaction lasted for 1.5 h. The reaction was carried out by HPLC. At the beginning of the reaction, the relative area percentage of 4-nitrophenol was shown to be 37.8% by HPLC analysis. The content of 4-nitrophenol decreased to 4.7% after the addition of 50% of the feedstock and further decreased to 5.0% after the addition of all the feedstock. Upon completion of the reaction, 8-bromo-5-fluoroquinoline was obtained after post-treatment in 87.5% yield with 0.29% total impurities. In addition, reducing the amount of 4-nitrophenol to 0.46 equivalents (34 g) was also successful in synthesizing the target intermediate in acceptable yield.

References

[1] Patent: US2007/27160, 2007, A1. Location in patent: Page/Page column 66
[2] Patent: US2007/299083, 2007, A1. Location in patent: Page/Page column 9
[3] Patent: WO2007/146072, 2007, A2. Location in patent: Page/Page column 73-74
[4] Patent: WO2008/67390, 2008, A2. Location in patent: Page/Page column 101-102
[5] Patent: US2007/27160, 2007, A1. Location in patent: Page/Page column 63-65

8-bromo-5-fluoroquinoline(917251-99-1)Related Product Information

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• methyl-8-bromoquinoline-5-carboxylate
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• 8-BroMo-4,4-diMethyl-3,4-dihydroquinolin-2(1H)-one
• Quinoline, 8-bromo-5-methyl- (9CI)
• 8-BROMO-4-CHLOROQUINOLINE
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• 8-bromo-5-fluoroquinoline