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Names | |||
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IUPAC name
4-Aminophenol | |||
Identifiers | |||
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3D model (JSmol) |
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ChEBI | |||
ChEMBL | |||
ChemSpider |
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ECHA InfoCard | 100.004.198 ![]() | ||
KEGG |
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MeSH | Aminophenols | ||
PubChem CID |
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UNII | |||
CompTox Dashboard (EPA) |
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Properties | |||
C6H7NO | |||
Molar mass | 109.126 g/mol | ||
Appearance | colorless to reddish-yellow crystals | ||
Density | 1.13 g/cm3 | ||
Melting point | 187.5 °C (369.5 °F; 460.6 K) | ||
Boiling point | 284 °C (543 °F; 557 K) | ||
1.5 g/100 mL (25 °C) | |||
Solubility | very soluble in dimethylsulfoxide soluble in acetonitrile ethyl acetate acetone slightly soluble in toluene, diethyl ether, ethanol negligible in benzene, chloroform | ||
log P | 0.04 | ||
Acidity (pKa) | 10.30 | ||
Structure | |||
orthorhombic | |||
Thermochemistry | |||
Std enthalpy of |
-190.6 kJ/mol | ||
Hazards | |||
NFPA 704 (fire diamond) | |||
Flash point | 195 °C (383 °F; 468 K) (cc) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
671 mg/kg | ||
Related compounds | |||
Related aminophenols |
2-Aminophenol 3-Aminophenol | ||
Related compounds |
Aniline Phenol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
4-Aminophenol (or para-aminophenol or p-aminophenol) is the organic compound with the formulaH2NC6H4OH. 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.
It is produced from phenolbynitration followed by reduction with iron. Alternatively, the partial hydrogenationofnitrobenzene affords phenylhydroxylamine, which rearranges primarily to 4-aminophenol:[2]
It can be produced from nitrobenzene by electrolytic conversion to phenylhydroxylamine, which spontaneously rearranges to 4-aminophenol.[3]
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:[4][5][6]