7-BROMO-2-METHYLQUINOLINE

7-BROMO-2-METHYLQUINOLINE Property

Melting point:

77-79 °C

Boiling point:

299.7±20.0 °C(Predicted)

Density 

1.488±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder

pka

4.25±0.50(Predicted)

color 

Light brown

Safety

Risk Statements 

41

Safety Statements 

26-39

HS Code 

2933499090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P271Use only outdoors or in a well-ventilated area.

7-BROMO-2-METHYLQUINOLINE Chemical Properties,Usage,Production

Chemical Properties

yellow powder

Synthesis

Doebner-Miller Synthesis: 3-Bromoaniline (10 mL, 92 mmol) was slowly added to a 37% hydrochloric acid solution (200 mL) pre-cooled to 0°C. Subsequently, trimeric acetaldehyde (11 mL, 0.8 mol, 9 equiv) was added dropwise to the reaction system. The reaction mixture was stirred at room temperature for 1 hour and then heated to reflux temperature to continue the reaction for 3 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and saturated aqueous sodium hydroxide solution (200 mL) was slowly added to neutralize the acidity. The reaction mixture was extracted with dichloromethane (200 mL x 3) and the organic phases were combined. The organic phase was washed with water and saturated saline in turn, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was a mixture of 5-bromoquinolidine and 7-bromoquinolidine, which was separated and purified by column chromatography (silica gel, cyclohexane-ethyl acetate=9:1) to obtain the 7-bromoquinolidine regiosemide as a light yellow solid (9.3 g, 46% yield). Molecular formula: C10H8BrN. molecular weight: 222.08 g/mol. IR (thin film method): 1610, 1494, 1264, 841, 736 cm-1. melting point: 57°C. 1H NMR (CDCl3): δ 8.09 (s, 1H, H8), 7.80 (d, J = 8.2 Hz, 1H, H4), 7.39 (m, 2H, H5 and H7). 2H, H5 and H7), 7.12 (d, J = 8.2 Hz, 1H, H3), 2.61 (s, 3H, H9).13C NMR (CDCl3): δ 160.3 (C2), 148.6 (C8a), 136.2 (C4), 131.2 (C8), 129.4 (C5), 128.9 (C6), 125.3 ( C4a), 123.7 (C7), 122.6 (C3), 25.7 (C9).

References

[1] Patent: EP2397466, 2011, A1. Location in patent: Page/Page column 12
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 41, p. 9708 - 9711
[3] Journal of the American Chemical Society, 1921, vol. 43, p. 2257
[4] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 6, p. 1615 - 1623