6-bromo-7-methylquinoline

6-bromo-7-methylquinoline Property

Density 

1.488

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to light brown Solid

Safety

HS Code 

2933499090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

6-bromo-7-methylquinoline Chemical Properties,Usage,Production

Chemical Properties

Yellow solid

Synthesis

General procedure for the synthesis of 6-bromo-7-methylquinoline from 4-bromo-3-methylaniline and glycerol: [0304] A mixture of 4-bromo-3-methylaniline (20 g, 107.5 mmol), ferric sulfate (6.6 g, 43.4 mmol), glycerol (40.8 g, 440 mmol) and nitrobenzene (8.12 g, 66 mmol) was mixed with concentrated sulfuric acid (23 ml) and slowly heated. After the initial vigorous reaction subsided, the reaction mixture was refluxed for 3 h. The excess nitrobenzene was subsequently removed by evaporation. The pH was adjusted to 7-8 by adding saturated aqueous sodium bicarbonate solution to the reaction mixture and then filtered. The filtrate was extracted with dichloromethane and the organic layers were combined and dried over anhydrous sodium sulfate. The dried organic phase was filtered and concentrated in vacuum and the resulting solid was purified by fast column chromatography. The purified yellow solid was further washed with petroleum ether to afford 7.5 g of 6-bromo-7-methylquinoline in 31% yield. The structure of the product was confirmed by 1H NMR (CDCl3): δ 2.60 (s, 3H), 7.36 (m, 1H), 7.96 (s, 1H), 8.04 (m, 2H), 8.89 (m, 1H).

References

[1] Patent: WO2008/51808, 2008, A2. Location in patent: Page/Page column 79-80