4-Aminophenol

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4-Aminophenol
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 123-30-8 YesY
MeSH Aminophenols
style="background: #F8EABA; text-align: center;" colspan="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)
style="background: #F8EABA; text-align: center;" colspan="2" | 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
style="background: #F8EABA; text-align: center;" colspan="2" | Related compounds
Related aminophenols 2-Aminophenol
3-Aminophenol
Related compounds Aniline
Phenol
 YesY (what is this?)  (verify)
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.

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

Reactions

p-Aminophenol reacts with acetic anhydride to give paracetamol.[3]

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References

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fr:4-aminophénol

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  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.