6-NITRO-2H-1,4-BENZOXAZIN-3(4H)-ONE

6-NITRO-2H-1,4-BENZOXAZIN-3(4H)-ONE Property

Melting point:

236-240 °C

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

color 

White to Orange to Green

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2914390090

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.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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-NITRO-2H-1,4-BENZOXAZIN-3(4H)-ONE Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 6-nitro-2H-1,4-benzoxazin-3(4H)-one from chloroacetyl chloride and 2-amino-4-nitrophenol was as follows: 1. 2-Amino-4-nitrophenol (6.0 g, 38.93 mmol) was dissolved in dichloromethane (200 mL) and the solution was cooled to 0°C. 2. To the cooled solution, triethylamine (16.3 mL, 116.9 mmol) and chloroacetyl chloride (3.42 mL, 42.8 mmol) were added sequentially with stirring, noting that the chloroacetyl chloride had to be added in small batches to avoid violent reaction. 3. After the addition of chloroacetyl chloride, the reaction mixture was gradually warmed up to room temperature and stirred for 18 hours to ensure complete reaction. 4. After completion of the reaction, the reaction mixture is diluted with additional dichloromethane and the organic phase is subsequently washed with water to remove water soluble impurities. 5. The organic phase was dried over anhydrous magnesium sulfate, filtered to remove the desiccant, and the filtrate was concentrated under reduced pressure to afford 6-nitro-4H-benzo[1,4]oxazin-3-one as 7.5 g solid in 100% yield.

References

[1] Patent: US2010/160373, 2010, A1. Location in patent: Page/Page column 30
[2] Patent: US2007/93477, 2007, A1. Location in patent: Page/Page column 20
[3] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 1, p. 222 - 236
[5] Patent: WO2018/19252, 2018, A1. Location in patent: Page/Page column 37