Nitrophenol

Nitrophenol

Nitrophenol

Chemical compound

Nitrophenols are compounds of the formula HOC6H5−x(NO2)x. The conjugate bases are called nitrophenolates. Nitrophenols are more acidic than phenol itself.[1]

Mono-nitrophenols

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with the formula HOC6H4NO2. Three isomeric nitrophenols exist:

  • o-Nitrophenol (2-nitrophenol; OH and NO2 groups are neighboring, a yellow solid.
  • m-Nitrophenol (3-nitrophenol, CAS number: 554-84-7), a yellow solid (m.p. 97 °C) and precursor to the drug mesalazine (5-aminosalicylic acid). It can be prepared by nitration of aniline followed by replacement of the amino group via its diazonium derivative.[2]

The mononitrated phenols are often hydrogenated to the corresponding aminophenols that are also useful industrially.[1]

Di- and trinitrophenols

2,4-dinitrophenol
picric acid
  • 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.[3]

References

  1. [1]
    Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
  2. [2]
    R. H. F. Manske (1928). "m-Nitrophenol". Organic Syntheses. 8: 80. doi:10.15227/orgsyn.008.0080.
  3. [3]
    Fact sheet at atsdr.cdc.gov
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