Puneet Varma (Editor)

Nitrophenol

Updated on
Edit
Like
Comment
Share on FacebookTweet on TwitterShare on LinkedInShare on Reddit
Nitrophenol 4Nitrophenol CAS 100027 106798

Relative acidity of o m and p nitrophenol mp4


Nitrophenols consist of a phenol molecule with one or more nitro-groups attached to the aromatic ring. The term is most often used to describe singly nitrated phenols.

Contents

Nitrophenol httpsuploadwikimediaorgwikipediacommonsthu

Lower pka p nitrophenol or m nitrophenol


Mono-nitrophenols

with the formula HOC6H4NO2. Three isomeric nitrophenols exist:

Nitrophenol 2Nitrophenol 98 SigmaAldrich

  • o-Nitrophenol (1-hydroxy-2-nitrobenzene; OH and NO2 groups are neighboring; CAS number: 88-75-5), a yellow crystalline solid (m.p. 46 °C).
  • m-Nitrophenol (1-hydroxy-3-nitrobenzene, CAS number: 554-84-7), a yellow solid (m.p. 97 °C) and precursor to the drug mesalazine (5-aminosalicylic acid).
  • p-Nitrophenol (1-hydroxy-4-nitrobenzene, CAS number: 100-02-7), yellow crystals (m.p. 114 °C). It is a precursor to the rice herbicide fluorodifen and the pesticide parathion.

    • The mononitrated phenols are often hydrogenated to the corresponding aminophenols that are also useful industrially.

    Di- and trinitrophenols

    Nitrophenol FilePNitrophenolsvg Wikipedia

    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

    Nitrophenol 4Nitrophenol ReagentPlus 99 SigmaAldrich

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

    Nitrophenol 4Nitrophenol C6H5NO3 ChemSpider

    Nitrophenol 5Methyl2nitrophenol 97 SigmaAldrich

    References

    Nitrophenol Wikipedia
    (Text) CC BY-SA