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[1])
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.198
KEGG
MeSH Aminophenols
UNII
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R-phrases (outdated) R20/21, R22, R40
R52, R54, R68
S-phrases (outdated) S28, S36, S37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
1
2
0
Flash point 195 °C (383 °F; 468 K) (cc)
Lethal dose or concentration (LD, LC):
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).
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Infobox references

4-Aminophenol (or para-aminophenol or p-aminophenol) is the organic compound with the formula H2NC6H4OH. Typically available as a white powder,[2] 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.

Preparation

From phenol

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:[3]

C6H5NO2 + 2 H2 → C6H5NHOH + H2O
C6H5NHOH → HOC6H4NH2

From nitrobenzene

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

Uses

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:[5][6][7]

  1. Parapropamol (4-HO-Ph-NHCOEt).
  2. Amidation with the acid chloride of ATRA gives Fenretinide.
  3. AM404 is made by acylating arachidonic acid.

See also

References

  1. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.
  2. ↑ CRC Handbook of Chemistry and Physics 65th Ed.
  3. ↑ Mitchell, S.C. & Waring, R.H. "Aminophenols." In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a02_099
  4. ↑ Polat, K.; Aksu, M.L.; Pekel, A.T. (2002), "Electroreduction of nitrobenzene to p-aminophenol using voltammetric and semipilot scale preparative electrolysis techniques", Journal of Applied Electrochemistry, Kluwer Academic Publishers, 32: 217–223, doi:10.1023/A:1014725116051
  5. ↑ Ellis, Frank (2002). Paracetamol: a curriculum resource. Cambridge: Royal Society of Chemistry. ISBN 0-85404-375-6.
  6. ↑ Anthony S. Travis (2007). "Manufacture and uses of the anilines: A vast array of processes and products". In Zvi Rappoport. The chemistry of Anilines Part 1. Wiley. p. 764. ISBN 978-0-470-87171-3.
  7. ↑ Elmar Friderichs; Thomas Christoph; Helmut Buschmann (2005), "Analgesics and Antipyretics", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a02_269.pub2
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