Nitrophenol

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

p-Nitrophenol

Mono-nitrophenols

with the formula HOC6H4NO2. Three isomeric nitrophenols exist:

  • o-Nitrophenol (2-nitrophenol; OH and NO2 groups are neighboring; CAS number: 88-75-5), a yellow crystalline solid (m.p. 46 °C).
  • 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).
  • p-Nitrophenol (4-nitrophenol, CAS number: 100-02-7), yellow crystals (m.p. 114 °C). It is a precursor to the rice herbicide fluorodifen, the pesticide parathion, and the human analgesic paracetamol (also known as acetaminophen).

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

Di- and trinitrophenols
2,4-dinitrophenol

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.[2][3] Occasionally, nitrophenols contaminate the soil near former explosives or fabric factories and military plants, and current research is aimed at remediation.

gollark: Communism is just a monoid in the category of endofunctors.
gollark: But it seems quite obvious that not giving people an incentive to do more things is bad, and that central control also runs into horrible problems.
gollark: I mean, people obviously quite like the idea of central economic planning for various fairly good reasons (not that communism means that now to a lot of people!).
gollark: It does not sound good "on paper" if you think about it for more than 5 seconds.
gollark: I know all information, actually.

References
  1. Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.
  2. Nitrophenol
  3. Dinitrophenol
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.