6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE Chemical Properties

Melting point:

>350 °C(Solv: ethanol (64-17-5))

Density 

1.475±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

9.59±0.20(Predicted)

form 

Solid

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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

29334900

MSDS

• Language:English Provider:ALFA

6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE Usage And Synthesis

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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