Nitrophenol

Preparation of 2- and 4-nitrophenol by steam distillation. 2-nitrophenol is yellow, 4-nitrophenol is brown.

Nitrophenols are a family of nitrated phenols with the formula HOC6H4NO2. Three isomeric nitrophenols exist:

The nitrophenols are produced industrially by the reaction of chlorides with sodium hydroxide at temperatures around 200 °C. The mononitrated phenols are often hydrogenated to the corresponding aminophenols that are also useful industrially.[1]

Di- and trinitrophenols

2,4-Dinitrophenol (m.p. 83 °C) is a moderately strong acid (pKa = 4.89). 2,4,6-trinitrophenol is better known as picric acid, which has a well-developed chemistry.

Safety

Nitrophenols are poisonous. Occasionally, nitrophenols contaminate the soil near former explosives or fabric factories and military plants, and current research is aimed at remediation.

References

  1. Gerald Booth "Nitro Compounds, Aromatic" in "Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_411

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