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

6-CHLORO-2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALINE Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

29334900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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

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