3-nitro-N-acrylphenylamine

3-nitro-N-acrylphenylamine Property

storage temp. 

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

Appearance

Off-white to yellow Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

3-nitro-N-acrylphenylamine Chemical Properties,Usage,Production

Synthesis

1. 3-Nitroaniline (6.90 g, 50 mmol) was weighed in a 250 mL round bottom flask, dichloromethane (100 mL) was added as solvent and stirring was initiated. 2. The reaction system was cooled to -78 °C and diisopropylethylamine (12.92 g, 100 mmol) was subsequently added to the reaction system. 3. Acryloyl chloride (6.80 g, 75 mmol) was slowly added dropwise to the reaction system under stirring conditions. 4. 4. After the dropwise addition, the reaction mixture was gradually warmed up to room temperature and the reaction was continued with stirring for 2 hours. 5. After completion of the reaction, the solvent was removed by concentration under reduced pressure to give the crude product. 6. The crude product was purified using column chromatography with the eluent being petroleum ether/ethyl acetate (4:1, v/v). 7. The target component was collected and the solvent was removed under reduced pressure to afford N-(3-nitrophenyl)acrylamide (9.6 g, 80% yield) as a yellow solid.

References

[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5505 - 5512
[2] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 444 - 455
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4179 - 4186
[4] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 765 - 772
[5] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1847 - 1857