4-Aminophenol

4-Aminophenol
IUPAC name

4-Aminophenol
Identifiers
CAS number 123-30-8 Y
PubChem 403
ChemSpider 392 Y
UNII R7P8FRP05V Y
KEGG C02372 Y
MeSH Aminophenols
ChEBI CHEBI:17602 Y
ChEMBL CHEMBL1142 Y
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C6H7NO
Molar mass 109.13 g/mol
Density 1.13 g/cm3
Melting point

188–190 °C
Boiling point

284 °C
Solubility in water 1.5 g/100 ml (25 °C)
Hazards
EU Index 616-003-00-0
EU classification Carc. Cat. 2
Muta. Cat. 2
Repr. Cat. 3
Toxic (T)
R-phrases R20/21, R22, R40
R52, R54, R68
S-phrases S28, S36, S37
S60, S61
NFPA 704
1
2
0
Flash point 195 °C
Related compounds
Related aminophenols 2-Aminophenol
3-Aminophenol
Related compounds Aniline
Phenol
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

4-Aminophenol is the organic compound with the formula H2NC6H4OH. Typically available as a white powder,[1] it is commonly used as a developer in black-and-white film, marketed under the name Rodinal.

Reflecting its slight hydrophilic character, the white powder is moderately soluble in alcohols and can be recrystallised from hot water. In the presence of base, it oxidizes readily. The N-methyl and N,N-dimethyl derivatives are of commercial value.

The compound is one of three isomeric aminophenols, the other two being 2-aminophenol and 3-aminophenol.

Contents

Preparation

It is produced from phenol by nitration followed by reduction with iron. Alternatively, the partial hydrogenation of nitrobenzene affords phenylhydroxylamine, which rearranges primarily to 4-aminophenol:[2]

C6H5NO2 + 2 H2 → C6H5NHOH + H2O
C6H5NHOH → HOC6H4NH2

Uses

p-Aminophenol is a building block compound. Prominently, it is the final intermediate in the industrial synthesis of paracetamol. Treating p-aminophenol with acetic anhydride gives paracetamol:[3][4][5]

References

  1. ^ CRC Handbook of Chemistry and Physics 65th Ed.
  2. ^ Mitchell, S.C. & Waring, R.H. “Aminophenols.” In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a02_099
  3. ^ Ellis, Frank (2002). Paracetamol: a curriculum resource. Cambridge: Royal Society of Chemistry. ISBN 0-85404-375-6. 
  4. ^ Anthony S. Travis (2007). "Manufacture and uses of the anilines: A vast array of processes and products". In Zvi Rappoport. The chemistry of Anilines Part 1. Wiley. p. 764. ISBN 978-0-470-87171-3. 
  5. ^ Elmar Friderichs, Thomas Christoph, Helmut Buschmann (2005), "Analgesics and Antipyretics", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a02_269.pub2