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4-Aminophenol

4-Aminophenol
Skeletal formula of 4-aminophenol
Space-filling model of the 4-aminophenol molecule
Names
Preferred IUPAC name
4-Aminophenol
Other names
p-Aminophenol (no longer recommended)
Identifiers
123-30-8 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:17602 YesY
ChEMBL ChEMBL1142 YesY
ChemSpider 392 YesY
ECHA InfoCard 100.004.198
KEGG C02372 YesY
MeSH Aminophenols
PubChem 403
UNII R7P8FRP05V YesY
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
-190.6 kJ/mol
Hazards
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
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored 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).
YesY  (what is YesYN ?)
Infobox references

4-Aminophenol (or para-aminophenol or p-aminophenol) is the organic compound with the formula H2NC6H4OH. Typically available as a white powder, it was commonly used as a developer for 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 phenol by nitration followed by reduction with iron. Alternatively, the partial hydrogenation of nitrobenzene affords phenylhydroxylamine, which rearranges primarily to 4-aminophenol:

It can be produced from nitrobenzene by electrolytic conversion to phenylhydroxylamine, which spontaneously rearranges to 4-aminophenol.

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:


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