5-BROMO-1,2,3,4-TETRAHYDRO-QUINOLINE HYDROCHLORIDE

5-BROMO-1,2,3,4-TETRAHYDRO-QUINOLINE HYDROCHLORIDE Property

Boiling point:

300℃

Density 

1.428

Flash point:

135℃

storage temp. 

2-8°C(protect from light)

pka

4.19±0.20(Predicted)

Appearance

Light yellow to brown Liquid

InChI

InChI=1S/C9H10BrN/c10-8-4-1-5-9-7(8)3-2-6-11-9/h1,4-5,11H,2-3,6H2

InChIKey

WTZQIKXLRRDMCP-UHFFFAOYSA-N

SMILES

N1C2=C(C(Br)=CC=C2)CCC1

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

5-BROMO-1,2,3,4-TETRAHYDRO-QUINOLINE HYDROCHLORIDE Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 5-bromo-1,2,3,4-tetrahydroquinoline from 4-bromoinden-1-one: 4-bromoinden-1-one (1.05 g, 5 mmol) was dissolved in methanol (14 ml), hydroxylamine hydrochloride (1.4 g, 20 mmol) was added, and the reaction was carried out at reflux for 1 hour. After completion of the reaction, vacuum concentration was carried out followed by addition of dichloromethane and 50% sodium bicarbonate solution and stirring for 20 min. The organic layer was separated, dried with anhydrous sodium sulfate and concentrated to give a white solid in 99% yield. The white solid (5 mmol) obtained above was dissolved in dichloromethane (30 ml), cooled to 0 °C and diisobutylaluminum hydride (20 ml, 30 mmol, 1.5 M toluene solution) was added slowly. The reaction mixture was stirred at 0°C for 30 min, then moved to room temperature and continued stirring overnight. After completion of the reaction, the reaction was quenched with water under ice bath conditions, extracted with dichloromethane, the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After concentration, it was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 3:1) to give 600 mg of 5-bromo-1,2,3,4-tetrahydroquinoline as a pale yellow solid in 56.6% yield.

References

[1] Patent: CN107814785, 2018, A. Location in patent: Paragraph 0062; 0081; 0082; 0083