7-bromoquinoxalin-2(1H)-one Chemical Properties

Density 

1.82±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

8.23±0.70(Predicted)

InChI

InChI=1S/C8H5BrN2O/c9-5-1-2-6-7(3-5)11-8(12)4-10-6/h1-4H,(H,11,12)

InChIKey

PXVQWJPOMIRXQL-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(Br)=C2)N=CC1=O

7-bromoquinoxalin-2(1H)-one Usage And Synthesis

Uses

7-Bromoquinoxalin-2(1H)-one was used to study preparation and serotoninmimetic activity of piperazinylquinoxalines.

Synthesis

General procedure for the synthesis of 7-bromo-2(1H)-quinoxalinone from 2-hydroxyquinoxaline: To a solution of quinoxalin-2(1H)-one (54.64 g, 374 mmol, 1.0 eq.) in acetic acid (1000 mL) was slowly added a solution of bromine (19.18 mL, 374 mmol, 1.0 eq.) in acetic acid (200 mL). The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the mixture was poured into ice water. The precipitate was collected by filtration and dried to afford 7-bromoquinoxalin-2(1H)-one as an off-white solid (74 g, 88% yield).

References

[1] Patent: WO2013/40515, 2013, A1. Location in patent: Paragraph 0288
[2] Patent: US2013/53384, 2013, A1. Location in patent: Paragraph 0470; 0471; 0472
[3] Patent: WO2013/112950, 2013, A2. Location in patent: Paragraph 0186
[4] Patent: WO2014/75077, 2014, A1. Location in patent: Paragraph 0174
[5] Patent: WO2010/84152, 2010, A1. Location in patent: Page/Page column 111-112

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