ChemicalBook--->CAS DataBase List--->89891-65-6

89891-65-6

89891-65-6 Structure

89891-65-6 Structure
IdentificationBack Directory
[Name]

7-Bromo-2-chloroquinoxaline
[CAS]

89891-65-6
[Synonyms]

7-BROMO-2-CHLOROQUINOXALINE
3-chloro-6-bromoquinoxaline
Quinoxaline, 7-bromo-2-chloro-
[Molecular Formula]

C8H4BrClN2
[MDL Number]

MFCD02955309
[MOL File]

89891-65-6.mol
[Molecular Weight]

243.49
Chemical PropertiesBack Directory
[Boiling point ]

312.5±37.0 °C(Predicted)
[density ]

1.762
[storage temp. ]

Inert atmosphere,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
Questions And AnswerBack Directory
[Uses]

7-Bromo-2-chloroquinoxaline is a heterocyclic derivative that can be used as an organic intermediate.
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H332-H335
[Precautionary statements ]

P261-P280-P305+P351+P338
[Hazard Codes ]

Xn
[Risk Statements ]

22
[HS Code ]

2933998090
Spectrum DetailBack Directory
[Spectrum Detail]

7-Bromo-2-chloroquinoxaline(89891-65-6)1HNMR
Hazard InformationBack Directory
[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
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