6-bromo-2-chloroquinoxaline Chemical Properties

Melting point:

150-152.5 °C

Boiling point:

312.5±37.0 °C(Predicted)

Density 

1.762±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-2.46±0.30(Predicted)

Appearance

Gray to brown Solid

InChI

InChI=1S/C8H4BrClN2/c9-5-1-2-6-7(3-5)11-4-8(10)12-6/h1-4H

InChIKey

XDJDRCGDVKTDHY-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

6-bromo-2-chloroquinoxaline Usage And Synthesis

Uses

6-Bromo-2-chloroquinoxaline is a quinoline derivative that can be used as a pharmaceutical intermediate.

Application

6-Bromo-2-chloroquinoxaline can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Preparation

From 6-bromo-2-hydroxyquinoxaline, tetra-n-butylammonium chloride and phosphorus pentoxide to toluene to react to obtain 6-bromo-2-chloroquinoxaline.

Synthesis

C. Synthesis of 6-bromo-2-chloroquinoxaline. 6-Bromoquinoxalin-2(1H)-one (255 mg, 1.1 mmol) from Step B was added to a reaction flask containing phosphorus trichloride (3.4 ml, 36.5 mmol). The reaction mixture was stirred and reacted at 60 °C overnight. After completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched by slowly pouring into ice water. The precipitated solid was collected by filtration and dried to give the target product 6-bromo-2-chloroquinoxaline (239 mg, 87% yield).

References

[1] ChemMedChem, 2014, vol. 9, # 7, p. 1378 - 1386
[2] Patent: WO2009/39134, 2009, A1. Location in patent: Page/Page column 185
[3] Patent: WO2016/199943, 2016, A1. Location in patent: Page/Page column 0288
[4] Patent: WO2010/136755, 2010, A1. Location in patent: Page/Page column 46; 47
[5] Journal of the American Chemical Society, 1949, vol. 71, p. 6,7

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