ChemicalBook--->CAS DataBase List--->917251-99-1

917251-99-1

917251-99-1 Structure

917251-99-1 Structure
IdentificationBack Directory
[Name]

8-bromo-5-fluoroquinoline
[CAS]

917251-99-1
[Synonyms]

8-bromo-5-fluoroquinoline
Quinoline, 8-bromo-5-fluoro-
[Molecular Formula]

C9H5BrFN
[MDL Number]

MFCD09907839
[MOL File]

917251-99-1.mol
[Molecular Weight]

226.05
Chemical PropertiesBack Directory
[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
Questions And AnswerBack Directory
[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.
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P280-P301+P312-P261
[HS Code ]

2933491090
Spectrum DetailBack Directory
[Spectrum Detail]

8-bromo-5-fluoroquinoline(917251-99-1)1HNMR
Hazard InformationBack Directory
[Synthesis]

2-Bromo-5-fluoroaniline

1003-99-2

Glycerol

56-81-5

8-bromo-5-fluoroquinoline

917251-99-1

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
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