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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Mono-nitrophenols
 
2-Nitrophenol (o-)
 
3-Nitrophenol (m-)
 
4-Nitrophenol (p-)
Identifiers
  • Compounds
  • oo-nitrophenol (2-)
  • mm-nitrophenol (3-)
  • pp-nitrophenol (4-)
  • pp tautomer
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
KEGG
UNII
  • o: InChI=1S/C6H5NO3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H
    Key: IQUPABOKLQSFBK-UHFFFAOYSA-N
  • m: InChI=1S/C6H5NO3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H
    Key: RTZZCYNQPHTPPL-UHFFFAOYSA-N
  • p: InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
    Key: BTJIUGUIPKRLHP-UHFFFAOYSA-N
  • o: Oc1ccccc1[N+]([O-])=O
  • m: Oc1cccc(c1)[N+]([O-])=O
  • p: c1cc(ccc1[N+](=O)[O-])O
  • p: O=[N+]([O-])c1ccc(O)cc1
Properties
C6H5NO3
Molar mass 139.110 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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2,4-dinitrophenol
 
picric acid
  • 2,4,6-Trinitrophenol is better known as picric acid, which has a well-developed chemistry.

Safety

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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

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  1. ^ a b 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. ^ R. H. F. Manske (1928). "m-Nitrophenol". Organic Syntheses. 8: 80. doi:10.15227/orgsyn.008.0080.
  3. ^ Fact sheet at atsdr.cdc.gov