2-Nitro-5-(phenylthio)aniline Chemical Properties

Melting point:

145-146 °C

Boiling point:

472.5±35.0 °C(Predicted)

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO, Methanol

form 

Solid

pka

-0.98±0.25(Predicted)

color 

Orange Yellow

EPA Substance Registry System

Benzenamine, 2-nitro-5-(phenylthio)- (43156-47-4)

2-Nitro-5-(phenylthio)aniline Usage And Synthesis

Uses

2-Nitro-5-phenylthioaniline is a useful synthetic intermediate. It was used to synthesize methyl 5(6)-phenylsulfinyl-2-benzimidazolecarbamate as a potent anthelmintic.

Synthesis

In an autoclave, 255 g of 5-chloro-2-nitroaniline (78.3% purity) was suspended in 250 mL of isopropanol. After warming the reaction system to 60 °C, 95.7 g of liquid ammonia was slowly pumped into the autoclave to bring the system pressure to 9 bar. this temperature was maintained, and 161 g of phenylthiophenol (98% purity) was added dropwise at a uniform rate over a period of 1.5 h, while the reaction pressure was controlled at a constant level of 9 bar by replenishing ammonia. after 6 h, the autoclave was cooled down to room temperature and slowly relieved of pressure. The reaction mixture was separated by filtration and the autoclave was rinsed with isopropyl alcohol and the rinsate was combined with the filtrate. The combined organic phases were washed with water and dried to obtain 298.6 g of the yellow powdery product 2-nitro-5-(phenylthio)aniline, which was analyzed by HPLC with a purity of 91.2% and a yield of 96.4% of the theoretical value.

References

[1] Patent: US6552230, 2003, B1
[2] Patent: US6552230, 2003, B1
[3] Archiv der Pharmazie, 1983, vol. 316, # 7, p. 638 - 638
[4] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 2, p. 273 - 276
[5] Patent: US3965113, 1976, A

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