ISOXAZOLE, 4-NITRO-

ISOXAZOLE, 4-NITRO- Property

Melting point:

46-47 °C

Boiling point:

243.5±13.0 °C(Predicted)

Density 

1.475±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-5.58±0.50(Predicted)

Appearance

Light brown to brown Solid

Safety

HS Code 

2934999090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

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

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

ISOXAZOLE, 4-NITRO- Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 4-nitroisoxazole from isoxazole: ammonium nitrate (1.8 g, 22.5 mmol) was added to a solution of trifluoroacetic anhydride (7 mL, 50.7 mmol) of isoxazole (1 g, 14.5 mmol) in batches of 0.3 g each, and the temperature of the reaction was controlled to be between 25 and 30 °C. After the addition was completed, the reaction mixture was slowly poured into ice water and extracted with dichloromethane (15 mL x 4). The organic phases were combined, washed with water and the aqueous layer was then extracted with dichloromethane. The combined dichloromethane extracts were dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a yellow-green oil. The oily material was ground with hexane under the condition of cooling to 50 ℃, a solid was precipitated, and 4-nitroisoxazole was obtained by filtration (0.72 g, 44% yield).

References

[1] Journal of Organic Chemistry, 1987, vol. 52, # 13, p. 2714 - 2726
[2] Helvetica Chimica Acta, 1989, vol. 72, p. 556 - 569
[3] Patent: WO2009/154769, 2009, A1. Location in patent: Page/Page column 37-38
[4] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 535,538; engl. Ausg. S. 533
[5] Patent: WO2011/38572, 2011, A1. Location in patent: Page/Page column 76