4-BROMO-7-CHLOROQUINOLINE

4-BROMO-7-CHLOROQUINOLINE Property

Melting point:

101-103°C

Boiling point:

331.3±22.0 °C(Predicted)

Density 

1.673

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, DMSO, Methanol

pka

1.81±0.27(Predicted)

form 

Solid

color 

Tan

Safety

Hazard Codes 

T

Risk Statements 

25-41

Safety Statements 

26-39-45

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2933499090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H318Causes serious eye damage

Precautionary statements

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

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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

4-BROMO-7-CHLOROQUINOLINE Chemical Properties,Usage,Production

Chemical Properties

yellow powder

Uses

4-Bromo-7-chloroquinoline is a chemical reagent in the synthesis of autophagy antitumor inhibitors, as well as antifungal agents.

Synthesis Reference(s)

The Journal of Organic Chemistry, 72, p. 2232, 2007 DOI: 10.1021/jo062168u

Synthesis

General procedure for the synthesis of 4-bromo-7-chloroquinoline from 4,7-dichloroquinoline: 4,7-dichloroquinoline (0.3315 g, 1.674 mmol) and propionitrile (3 mL) were added in a 20 mL microwave tube, followed by the slow addition of trimethylsilyl bromide (TMS-Br, 0.434 mL, 3.35 mmol) at room temperature. Precipitation generation was observed during the reaction. The reaction tube was sealed and placed in a 100 °C oil bath for 12 hours. After completion of the reaction, the system was cooled to room temperature. The crude reaction mixture was slowly poured into pre-cooled sodium hydroxide solution (1 N, 3 mL) and the reaction tube was rinsed with an appropriate amount of water. Subsequently, the aqueous layer was extracted with ether (3 x 5 mL). All ether layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to afford the target product 4-bromo-7-chloroquinoline (300 mg, 1.126 mmol, 67% yield) as a yellow solid. The product was confirmed by NMR hydrogen spectrum (400 MHz, CDCl3): δ 8.70 (d, J = 4.6 Hz, 1H), 8.17 (d, J = 8.8 Hz, 1H), 8.14 (d, J = 2.0 Hz, 1H), 7.73 (d, J = 4.6 Hz, 1H), 7.63 (dd, J = 9.0, 2.0 Hz, 1H); liquid chromatography-mass spectrometry (LCMS, ESI) showed a molecular ion peak m/z of 241.9, which is consistent with the calculated value of C9H5BrClN.

References

[1] European Journal of Organic Chemistry, 2002, # 24, p. 4181 - 4184
[2] Journal of the American Chemical Society, 1959, vol. 81, p. 3984,3986
[3] Patent: WO2017/59085, 2017, A1. Location in patent: Page/Page column 224; 225