4-Aminophenol
| 4-Aminophenol | |
|---|---|
| 4-Aminophenol | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 123-30-8 
|
| 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 | |
| Flash point | 195 °C |
| style="background: #F8EABA; text-align: center;" colspan="2" | Related compounds | |
| Related aminophenols | 2-Aminophenol 3-Aminophenol |
| Related compounds | Aniline Phenol |
 (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.
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
Reactions
p-Aminophenol reacts with acetic anhydride to give paracetamol.[3]
References
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<references />, or <references group="..." />- ↑ 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.
