5-CHLORO-3,1-BENZOXAZIN-2,4-DIONE Chemical Properties

Melting point:

272.5-272.9 °C

Density 

1.540±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

10.27±0.20(Predicted)

form 

lumpy powder

color 

Faint pink

Safety Information

HS Code 

2934999090

5-CHLORO-3,1-BENZOXAZIN-2,4-DIONE Usage And Synthesis

Synthesis

In a 250 mL round-bottomed flask under nitrogen protection, 2-amino-6-chlorobenzoic acid (11.69 g, 68 mmol) was dissolved in 100 mL of 1,4-dioxane. After cooling the reaction system to 0°C, phosgene (36 mL, 68 mmol) was slowly added through a dropping funnel. The reaction mixture was stirred at 0°C for 24 h, followed by natural warming to 23°C (room temperature). Upon completion of the reaction, the resulting white solid product was collected by filtration and washed sequentially with 1,4-dioxane and ether to afford 5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (12.5 g, 93% yield).

References

[1] Organic Process Research and Development, 2007, vol. 11, # 4, p. 674 - 680
[2] Patent: US2007/249605, 2007, A1. Location in patent: Page/Page column 8
[3] Patent: US2004/162285, 2004, A1
[4] Patent: US2004/87577, 2004, A1. Location in patent: Page 65
[5] Patent: US2004/167123, 2004, A1. Location in patent: Page/Page column 98

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