8-BROMO-6-METHOXYQUINOLINE

8-BROMO-6-METHOXYQUINOLINE Property

Melting point:

65-66 °C

Boiling point:

329.0±22.0 °C(Predicted)

Density 

1.516±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

2.38±0.20(Predicted)

Appearance

Gray to brown Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

8-BROMO-6-METHOXYQUINOLINE Chemical Properties,Usage,Production

Synthesis

Step 5 Synthesis of 8-bromo-6-methoxyquinoline: To a solution of 5.05 g (29.0 mmol) of 6-methoxy-8-aminoquinoline in 25 mL of 48% hydrobromic acid (HBr) was added a 20 mL aqueous solution of 2.60 g (37.7 mmol) of sodium nitrite (NaNO2) at 0 °C. After stirring at 0°C for 15 minutes, the resulting mixture was added dropwise to a solution of 5.0 g (34.8 mmol) of cuprous bromide (CuBr) and 60 mL of 48% hydrobromic acid (HBr) preheated to 75°C. After 5.5 hours of reaction, the reaction mixture was neutralized with 150 mL of ice-cold 5N sodium hydroxide (NaOH) solution, followed by stirring the resulting mixture with 300 mL of ethyl acetate (EtOAc) and filtration through a diatomaceous earth pad. The filtrate was extracted with 2 x 100 mL of ethyl acetate (EtOAc), the organic phases were combined, washed sequentially with 1 x 200 mL of water (H2O), 1 x 200 mL of brine, dried with anhydrous sodium sulfate (Na2SO4), and the volatiles were evaporated after filtration. The resulting crude product was purified by column chromatography on silica gel (SiO2) with the eluent of petroleum ether/ethyl acetate (4/1 to 1/1) to afford 4.23 g (17.8 mmol, 61% yield) of the target compound 8-bromo-6-methoxyquinoline as a brown oil. Mass spectrum (ES) m/z 239 (MH)+.

References

[1] Patent: US2003/32645, 2003, A1
[2] Zhurnal Obshchei Khimii, 1941, vol. 11, p. 537,538
[3] Chem.Abstr., 1941, p. 6961
[4] Journal of the American Chemical Society, 1951, vol. 73, p. 4837