7-Bromo-3-chloroquinoline

7-Bromo-3-chloroquinoline Property

Boiling point:

314.5±22.0 °C(Predicted)

Density 

1.673±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

0.99±0.25(Predicted)

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.

7-Bromo-3-chloroquinoline Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 7-bromo-3-chloroquinoline from 2-amino-4-bromobenzaldehyde and chloroacetaldehyde diethyl acetal: 2-chloro-1,1-diethoxyethane (4.50 mL, 30.0 mmol), 2-amino-4-bromobenzaldehyde (3.00 g, 15.0 mmol), and p-toluenesulfonic acid monohydrate (0.285 g, 1.500 mmol) were dissolved in toluene (50 mL), assembled with a Dean-Stark manifold, and heated to reflux at 110 °C for 3 hours. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate. The aqueous layer was then extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate and concentrated to dryness. The crude product was purified by silica gel column chromatography with 20-50% dichloromethane/hexane as eluent to give the title compound 7-bromo-3-chloroquinoline (1.97 g, 8.12 mmol, 54% yield) as a yellow solid. Mass spectrum (ESI+) m/e 241.8/243.8 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 7.85 (dd, J = 8.84, 2.02 Hz, 1H), 7.98 (d, J = 8.59 Hz, 1H), 8.29 (d, J = 1.77 Hz, 1H), 8.65 (d, J = 2.02 Hz, 1H), 8.94 (d, J = 2.53 Hz, 1H).

References

[1] Patent: WO2014/108858, 2014, A1. Location in patent: Page/Page column 37, 38