6-bromo-8-nitroquinoline

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Company Name: Amkchem Limited  Gold
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6-bromo-8-nitroquinoline Basic information
Product Name:6-bromo-8-nitroquinoline
Synonyms:6-bromo-8-nitroquinoline;Quinoline, 6-bromo-8-nitro-
CAS:68527-67-3
MF:C9H5BrN2O2
MW:253.05
EINECS:
Product Categories:
Mol File:68527-67-3.mol
6-bromo-8-nitroquinoline Structure
6-bromo-8-nitroquinoline Chemical Properties
Melting point 170-177 °C
Boiling point 365.8±27.0 °C(Predicted)
density 1.747±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka0.41±0.20(Predicted)
AppearanceYellow to brown Solid
EPA Substance Registry System6-Bromo-8-nitroquinoline (68527-67-3)
Safety Information
TSCA TSCA listed
MSDS Information
6-bromo-8-nitroquinoline Usage And Synthesis
Chemical Propertiesyellow powder
Synthesis
4-Bromo-2-nitroaniline

875-51-4

Ethylene glycol

107-21-1

6-bromo-8-nitroquinoline

68527-67-3

1. Add H2O (20 mL) to a 250 mL flask and place in an ice bath to cool. H2SO4 (50 mL) was added slowly to prepare a sulfuric acid solution. 2. To the above sulfuric acid solution, glycerol (12 mL, 16.5 mmol), m-nitrobenzenesulfonic acid sodium salt (11.4 g, 5.06 mmol), and 4-bromo-2-nitroaniline (10 g, 4.6 mmol) were added sequentially. 3. The reaction mixture was heated to 135 °C with continuous stirring for 3 hours. 4. Upon completion of the reaction, the warmed reaction mixture was slowly poured into ice H2O (200 mL). 5. The reaction mixture was extracted with 50% MeOH/EtOAc solvent mixture (2 x 200 mL). 6. The organic phases were combined and dried with Na2SO4, followed by concentration of the organic phase. 7. The resulting brown solid was ground with EtOH and filtered to give the pink solid product 6-bromo-8-nitroquinoline (3.8 g, 33% yield) with a melting point of 172-174 °C.

References[1] Patent: EP1147083, 2004, B1. Location in patent: Page 45-46
6-bromo-8-nitroquinoline Preparation Products And Raw materials
Raw materials4-Bromo-2-nitroaniline-->Ethylene glycol-->Glycerol-->Sodium 3-nitrobenzenesulphonate-->Sulfuric acid
Preparation Products6-Methyl-8-nitroquinoline
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