7-Bromo-2-chloroquinoxaline

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Company Name: Chongqing AoShe Biological Chemical Co., Ltd.  Gold
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7-Bromo-2-chloroquinoxaline manufacturers

7-Bromo-2-chloroquinoxaline Basic information
Uses
Product Name:7-Bromo-2-chloroquinoxaline
Synonyms:7-BROMO-2-CHLOROQUINOXALINE;3-chloro-6-bromoquinoxaline;Quinoxaline, 7-bromo-2-chloro-
CAS:89891-65-6
MF:C8H4BrClN2
MW:243.49
EINECS:
Product Categories:
Mol File:89891-65-6.mol
7-Bromo-2-chloroquinoxaline Structure
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)
AppearanceOff-white to light brown Solid
InChIInChI=1S/C8H4BrClN2/c9-5-1-2-6-7(3-5)12-8(10)4-11-6/h1-4H
InChIKeyAZUMKBQKUXTHCM-UHFFFAOYSA-N
SMILESN1C2C(=CC=C(Br)C=2)N=CC=1Cl
Safety Information
Hazard Codes Xn
Risk Statements 22
HS Code 2933998090
MSDS Information
7-Bromo-2-chloroquinoxaline Usage And Synthesis
Uses7-Bromo-2-chloroquinoxaline is a heterocyclic derivative that can be used as an organic intermediate.
Synthesis
7-bromoquinoxalin-2(1H)-one

82031-32-1

7-Bromo-2-chloroquinoxaline

89891-65-6

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 Preparation Products And Raw materials
Raw materialsEthyl glyoxalate-->7-bromoquinoxalin-2(1H)-one-->o-Phenylenediamine-->Ethyl acetate-->Sodium bicarbonate
Preparation Products7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline
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