6-BROMO-4-CHLOROQUINOLINE Chemical Properties

Melting point:

110-112℃

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

solubility 

soluble in Toluene

form 

solid

pka

2.76±0.16(Predicted)

Appearance

White to light yellow Solid

InChI

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

InChIKey

KJILYZMXTLCPDQ-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

T

Risk Statements 

25-20/22

Safety Statements 

45-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29334900

6-BROMO-4-CHLOROQUINOLINE Usage And Synthesis

Chemical Properties

Light yellow to yellow powder

Uses

6-Bromo-4-chloroquinoline belongs to the class of heterocyclic compounds and has been used in the synthesis of other compounds, such as pharmaceuticals.

Synthesis

4.1.8 Synthesis of 6-bromo-4-chloroquinoline (11) To a 100 mL round bottom flask were sequentially added 6-bromo-4-hydroxyquinoline (10) (3.0 g, 13.45 mmol), phosphorus trichloride (20 mL) and N,N-dimethylformamide (0.5 mL). The reaction mixture was heated to reflux and stirred for 6 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was slowly poured into ice water (100 mL) and stirring was continued for 1 hour. Subsequently, the pH of the mixture was adjusted with saturated aqueous sodium bicarbonate solution to 8. The reaction mixture was extracted with ethyl acetate, the organic phases were combined and dried with anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to give the title compound 6-bromo-4-chloroquinoline (11) (2.75 g, 11.36 mmol, 84% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.87 (d, J = 4.5 Hz, 1H, Ar-H), 8.32 (d, J = 2.0 Hz, 1H, Ar-H), 8.03 (d, J = 9.0 Hz, 1H, Ar-H), 7.99 (dd, J = 9.0, 2.0 Hz, 1H, Ar-H), 7.82 (d, J = 4.5 Hz, 1H, Ar-H). ESI-MS: m/z = 242 [M + H]+.

References

[1] Patent: US2006/63805, 2006, A1. Location in patent: Page/Page column 9
[2] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[3] Patent: US2015/320727, 2015, A1. Location in patent: Paragraph 0557; 0558
[4] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[5] Patent: WO2006/132739, 2006, A2. Location in patent: Page/Page column 48

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