7-BROMO-4-CHLOROQUINOLINE Chemical Properties

Melting point:

105-106 °C

Boiling point:

314.6±22.0 °C(Predicted)

Density 

1.673±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

1.99±0.27(Predicted)

color 

Beige

InChI

InChI=1S/C9H5BrClN/c10-6-1-2-7-8(11)3-4-12-9(7)5-6/h1-5H

InChIKey

JJUTYYVZDKDLBC-UHFFFAOYSA-N

SMILES

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

Safety Information

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

7-BROMO-4-CHLOROQUINOLINE Usage And Synthesis

Chemical Properties

yellow powder

Synthesis

General procedure for the synthesis of 4-chloro-7-bromoquinoline from 4-hydroxy-7-bromoquinoline: Phosphorus oxychloride (106.76 g, 696.28 mmol) was added in batches to a solution of dioxane (660 mL) containing 4-hydroxy-7-bromoquinoline (60 g, 267.8 mmol) at 30 °C. The reaction mixture was stirred at 100 °C for 40 min before confirming that 4-hydroxy-7-bromoquinoline had been completely converted to 4-chloro-7-bromoquinoline by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the reaction was quenched with water (200 mL) and subsequently extracted with ethyl acetate (200 mL x 2). The combined organic phases were washed with saturated sodium chloride solution (100 mL x 2) and dried with anhydrous sodium sulfate. After concentration under reduced pressure, the target compound 4-chloro-7-bromoquinoline (light yellow solid, 59 g, 81.77% yield) was obtained. It was analyzed by liquid chromatography-mass spectrometry (LC-MS, ESI), and the molecular ion peak m/z was 243.8 ([M+H]+).

References

[1] Patent: EP3293177, 2018, A1. Location in patent: Paragraph 0459; 0460
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 3236
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 113,115
[4] Journal of Medicinal Chemistry, 1998, vol. 41, # 25, p. 4918 - 4926
[5] Patent: WO2018/34918, 2018, A1. Location in patent: Page/Page column 71

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