| Identification | Back Directory | [Name]
6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE | [CAS]
6639-79-8 | [Synonyms]
6-CHLOROQUINOXAZALONE
6-CHLOROQUINOXALINE-2,3-DIOL
6-Chloro-2,3-dihydroxyqunoxaline
6-Chloro-2,3-dihydroxyquinoxaline
2,3-DIHYDROXY-6-CHLOROQUINOXALINE
1-(2-chloroethoxy)-2-phenylbenzene
2,3-Dihydroxy-6-chloroquinoxaline ,97%
6-chloro-1,4-dihydro-3-quinoxalinedione
6-chloro-1,4-dihydroquinoxaline-2,3-dione
6-CHLORO-1,4-DIHYDRO-2,3-QUINOXALINEDIONE
2,3-Quinoxalinedione, 6-chloro-1,4-dihydro-
6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE
6-chloro-1,2,3,4-tetrahydroquinoxaline-2,3-dione | [EINECS(EC#)]
229-647-9 | [Molecular Formula]
C8H5ClN2O2 | [MDL Number]
MFCD00047592 | [MOL File]
6639-79-8.mol | [Molecular Weight]
196.59 |
| Chemical Properties | Back Directory | [Melting point ]
>350 °C(Solv: ethanol (64-17-5)) | [density ]
1.475±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
Solid | [pka]
9.59±0.20(Predicted) | [Appearance]
Brown to dark brown Solid | [InChI]
InChI=1S/C8H5ClN2O2/c9-4-1-2-5-6(3-4)11-8(13)7(12)10-5/h1-3H,(H,10,12)(H,11,13) | [InChIKey]
RNOLFZACEWWIHP-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(Cl)C=C2)NC(=O)C1=O | [EPA Substance Registry System]
2,3-Quinoxalinedione, 6-chloro-1,4-dihydro- (6639-79-8) |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white solid | [Uses]
6-Chloroquinoxaline-2,3-diol can be used as glycine receptor antagonists to use as analgesics, anticonvulsants, neuroprotectants, and sedative-?hypnotics. | [Synthesis]
Step 1: Synthesis of 6-chloroquinoxaline-2,3(1H,4H)-dione
To a 100 mL round bottom flask was added 4-chloro-1,2-phenylenediamine (5.3 g, 37 mmol) and diethyl oxalate (31 mL). The reaction mixture was stirred under reflux conditions overnight. The reaction progress was monitored by thin layer chromatography (TLC, spreading agent ratio ethyl acetate/petroleum ether = 1:10). Upon completion of the reaction, the precipitate was collected by filtration, washed with ethanol (20 mL) and dried to give 7.0 g of light yellow solid product in 96% yield. The product was characterized as follows: 1H NMR (300 MHz, DMSO-d6) δ: 11.96 (br, 2H), 7.11 (m, 3H); MS m/z: 195 (M-H+). | [References]
[1] Journal of Medicinal Chemistry, 1990, vol. 33, # 8, p. 2240 - 2254
[2] Patent: US2010/120741, 2010, A1. Location in patent: Page/Page column 17
[3] Patent: WO2011/112731, 2011, A2. Location in patent: Page/Page column 66
[4] Journal of Organic Chemistry, 2017, vol. 82, # 19, p. 10077 - 10091
[5] Synthetic Communications, 2004, vol. 34, # 8, p. 1349 - 1357 |
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