8-BROMO-2-METHYL-QUINOLINE Chemical Properties

Melting point:

63-65℃

Boiling point:

132°C/0.1mmHg(lit.)

Density 

1.488

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

3.17±0.50(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C10H8BrN/c1-7-5-6-8-3-2-4-9(11)10(8)12-7/h2-6H,1H3

InChIKey

GQPRZSFQSOEDNV-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2Br)C=CC=1C

CAS DataBase Reference

61047-43-6

Safety Information

HS Code 

2933.49.7000

8-BROMO-2-METHYL-QUINOLINE Usage And Synthesis

Uses

8-Bromo-2-methylquinoline is a quinoline derivative that can be used as a pharmaceutical intermediate.

Synthesis

To a 6N hydrochloric acid (300 mL) solution of o-bromoaniline (100 g, 0.58 mol) was slowly added trans-2-butenal (81 g, 1.1 mol) at room temperature. The reaction mixture was heated to 100 °C and stirred overnight. Upon completion of the reaction, the mixture was cooled to room temperature, alkalized to pH 8-9 with ammonium hydroxide solution and subsequently extracted with ether (3 × 100 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with petroleum ether/ethyl acetate (12:1 to 10:1, v/v) as eluent to afford 8-bromo-2-methylquinoline as a white solid (59 g, 54% yield). Mass spectrometry (ESI) analysis: calculated value for C10H8BrN was 222.1; measured value was 223 [M + H]+.

References

[1] Patent: WO2010/101949, 2010, A1. Location in patent: Page/Page column 116; 117
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 4066 - 4084
[3] Patent: WO2009/80675, 2009, A1. Location in patent: Page/Page column 14
[4] Arkivoc, 2015, vol. 2015, # 3, p. 38 - 51

8-BROMO-2-METHYL-QUINOLINE(61047-43-6)Related Product Information

• 6-Bromoquinoline
• 5-Bromoquinoline
• 8-Methylquinoline
• 4-methylquinoline