N-METHYL-4-NITRO-O-TOLUIDINE Chemical Properties

Melting point:

138 °C

Boiling point:

310.3±30.0 °C(Predicted)

Density 

1.212±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

very faint turbidity in hot Methanol

form 

powder to crystal

pka

0.51±0.12(Predicted)

color 

Light yellow to Yellow to Orange

Safety Information

HS Code 

2921490090

N-METHYL-4-NITRO-O-TOLUIDINE Usage And Synthesis

Synthesis

1. Preparation of N-methyl-2-methyl-4-nitroaniline from N-formyl-2-methyl-4-nitroaniline: 18 g (0.1 mol) of N-formyl-2-methyl-4-nitroaniline was dissolved in 500 ml of dry tetrahydrofuran. 200 ml of tetrahydrofuran solution of 1 mole of borane/tetrahydrofuran complex was slowly added dropwise at 0 °C for 45 min. The reaction mixture was gradually warmed up to room temperature and subsequently refluxed for 1 hour. Upon completion of the reaction, the mixture was cooled to 0°C and hydrolyzed by adding 130 ml of water. Tetrahydrofuran was removed by evaporation and the residue was dissolved in 300 ml of 6N hydrochloric acid and refluxed for 2.5 hours. After cooling, the solution was poured into 1 liter of ice water and the yellow precipitate was obtained by filtration. The precipitate was washed with water, dried under reduced pressure at 50 °C and finally recrystallized from ethanol to give 15.8 g of N-methyl-2-methyl-4-nitroaniline (yield: 95%). The recrystallized product was suitable for further preparation of target compounds I-8.

References

[1] Patent: US5103060, 1992, A
[2] Australian Journal of Chemistry, 1984, vol. 37, # 5, p. 1009 - 1021

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