6-BROMO-2-CHLORO-QUINOLINE Chemical Properties

Melting point:

148-150℃

Boiling point:

325.7±22.0 °C(Predicted)

Density 

1.673±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Soluble in Chloroform and Methanol

form 

Solid

pka

-0.48±0.43(Predicted)

color 

White Crystalline

InChI

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

InChIKey

YXRDWUJAJLDABJ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

1810-71-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

HS Code 

2933499090

6-BROMO-2-CHLORO-QUINOLINE Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

It is used as a pharmaceutical intermediate.

Synthesis

Step 1: 6-Bromoquinolin-2(1H)-one (1.0 g, 4.4 mmol, 1.0 eq.) was dissolved in phosphoryl chloride (15 mL), stirred and heated to 100 °C, and reacted for 15 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and water was added to the residue. The precipitated solid was collected by filtration and dried under vacuum to give 6-bromo-2-chloroquinoline as a pink solid (1.0 g, 92% yield).LC-MS (ES) m/z = 241.0, 243.0 [M + H]+.1H NMR (400 MHz, DMSO-d6) δ ppm: 7.41 (d, J = 8.4 Hz, 1H), 7.79-7.82 ( m, 1H), 7.89 (d, J = 9.2 Hz, 1H), 7.98-7.99 (m, 1H), 8.02 (d, J = 8.8 Hz, 1H).

References

[1] Patent: WO2017/46739, 2017, A1. Location in patent: Page/Page column 78
[2] Journal of the American Chemical Society, 2016, vol. 138, # 25, p. 7808 - 7811
[3] Patent: WO2006/132739, 2006, A2. Location in patent: Page/Page column 36
[4] European Journal of Medicinal Chemistry, 2000, vol. 35, # 10, p. 931 - 940
[5] Patent: WO2009/39127, 2009, A1. Location in patent: Page/Page column 181

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