7-Bromo-2-chloroquinoxaline Chemical Properties

Boiling point:

312.5±37.0 °C(Predicted)

Density 

1.762

storage temp. 

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

pka

-2.50±0.30(Predicted)

Appearance

Off-white to light brown Solid

InChI

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

InChIKey

AZUMKBQKUXTHCM-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933998090

7-Bromo-2-chloroquinoxaline Usage And Synthesis

Uses

7-Bromo-2-chloroquinoxaline is a heterocyclic derivative that can be used as an organic intermediate.

Synthesis

General procedure for the synthesis of 7-bromo-2-chloroquinoxaline from 7-bromo-2(1H)-quinoxalinone: 7-bromoquinoxalin-2-ol (2 g, 8.88 mmol) was added to dry phosphorus trichloride (7 mL) to form a suspension, followed by the addition of N,N-dimethylformamide (DMF, 2 drops). The reaction mixture was heated to 100 °C and the reaction was stirred at this temperature for 3 hours. After completion of the reaction, the mixture was cooled to room temperature. Excess phosphorous trichloride was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (EtOAc) and added slowly dropwise to ice water under stirring. The aqueous phase was extracted three times with ethyl acetate, the organic layers were combined and washed with saturated sodium bicarbonate (NaHCO3) solution. Finally, the organic layer was concentrated to give 7-bromo-2-chloroquinoxaline as a solid product in 93% (2 g) yield.

References

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4735 - 4751
[2] Patent: WO2012/34526, 2012, A1. Location in patent: Page/Page column 34-35
[3] Patent: US2013/190307, 2013, A1. Location in patent: Paragraph 0162; 0164
[4] Patent: WO2017/32840, 2017, A1. Location in patent: Page/Page column 280
[5] Patent: WO2014/151147, 2014, A1. Location in patent: Paragraph 00641

7-Bromo-2-chloroquinoxaline(89891-65-6)Related Product Information

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