4-Aminophenol
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| Names | |||
|---|---|---|---|
| IUPAC name
4-Aminophenol
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| Identifiers | |||
| ECHA InfoCard | 100.004.198 | ||
| MeSH | Aminophenols | ||
CompTox Dashboard (EPA)
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| Properties | |||
| C6H7NO | |||
| Molar mass | 109.13 g/mol | ||
| Density | 1.13 g/cm3 | ||
| Melting point | 188–190 °C | ||
| Boiling point | 284 °C | ||
| 1.5 g/100 ml (25 °C) | |||
| Hazards | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 195 °C | ||
| Related compounds | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
References
- ^ CRC Handbook of Chemistry and Physics 65th Ed.
- ^ Mitchell, S.C. & Waring, R.H. “Aminophenols.” In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a02_099
- ^ Ellis, Frank (2002). Paracetamol: a curriculum resource. Cambridge: Royal Society of Chemistry. ISBN 0-85404-375-6.