4-Aminophenol

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4-Aminophenol
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Names
Preferred IUPAC name
4-Aminophenol[1]
Other names
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  • p-Aminophenol
  • para-Aminophenol
Identifiers
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3D model (JSmol)
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385836
ChEBI Page Template:Plainlist/styles.css has no content.
ChEMBL Page Template:Plainlist/styles.css has no content.
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EC Number Page Template:Plainlist/styles.css has no content.
2926
KEGG Page Template:Plainlist/styles.css has no content.
MeSH Aminophenols
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UNII Page Template:Plainlist/styles.css has no content.
UN number 2512
  • InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 checkY
    Key: PLIKAWJENQZMHA-UHFFFAOYSA-N checkY
  • InChI=1/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2
    Key: PLIKAWJENQZMHA-UHFFFAOYAD
  • Oc1ccc(N)cc1
  • c1cc(ccc1N)O
Properties
C6H7NO
Molar mass 109.128 g·mol−1
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
Solubility Template:Bulletedlist
log P 0.04
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  • 5.48 (amino; H2O)
  • 10.30 (phenol; H2O)[2]
Structure
orthorhombic
Thermochemistry
−190.6 kJ/mol
Hazards
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2
1
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).

Template:Chembox Footer/trackingTemplate:Short description

4-Aminophenol (or para-aminophenol or p-aminophenol) is an organic compound with the formula H2NC6H4OH. It is a metabolite of acetaminophen which the body converts to N-arachidonoylphenolamine and this compound is responsible for all or part of acetaminophen's analgesic action[3] and anticonvulsant effects.[4].

Commercially available as a white powder,[5] it is commonly used as a developer for black-and-white film, marketed under the name Rodinal.

Reflecting its slightly hydrophilic character, the white powder is moderately soluble in alcohols and can be recrystallized from hot water. In the presence of a base, it oxidizes readily. The methylated derivatives N-methylaminophenol and N,N-dimethylaminophenol are of commercial value.

The compound is one of three isomeric aminophenols, the other two being 2-aminophenol and 3-aminophenol.

Preparation

4-Aminophenol can be prepared by several routes. One route is hydrogenation of 4-nitrophenol over Raney nickel.[6]

HOC6H4NO2 + 3 H2 → HOC6H4NH2 + 2 H2O

The nitrophenol can also be reduced by iron or by stannous chloride.[7][8]

4-Aminophenol can be produced by reduction of nitrobenzene via the intermediate phenylhydroxylamine, which spontaneously rearranges to 4-aminophenol.[9][6]

C6H5NHOH → HOC6H4NH2

Uses

4-Aminophenol is a building block used in organic chemistry. Prominently, it is the final intermediate in the industrial synthesis of paracetamol. Treating 4-aminophenol with acetic anhydride gives paracetamol:[10][11][12]

It is a precursor to amodiaquine, mesalazine, AM404, parapropamol, B-86810 & B-87836 (cf. Page Template:Citation/styles.css has no content.WO 2001042204 ).

4-Aminophenol converts readily to the diazonium salt.[13]

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Ottani A, Leone S, Sandrini M, Ferrari A, Bertolini A (February 2006). "The analgesic activity of paracetamol is prevented by the blockade of cannabinoid CB1 receptors". European Journal of Pharmacology. 531 (1–3): 280–281. doi:10.1016/j.ejphar.2005.12.015. PMID 16438952.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Deshpande LS, DeLorenzo RJ (January 2011). "Acetaminophen inhibits status epilepticus in cultured hippocampal neurons". NeuroReport. 22 (1): 15–18. doi:10.1097/WNR.0b013e3283413231. PMC 3052417. PMID 21037491.
  5. ^ CRC Handbook of Chemistry and Physics 65th Ed.
  6. ^ a b Page Module:Citation/CS1/styles.css has no content.Mitchell, Stephen C.; Waring, Rosemary H. (2000). "Aminophenols". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_099. ISBN 978-3-527-30385-4.
  7. ^ Page Template:Citation/styles.css has no content.US2998450A, Godfrey, Wilbert & De, Angelis John, "Process of preparing nu-acetyl-p-amino phenol", issued Script error: No such module "auto date formatter". 
  8. ^ Page Module:Citation/CS1/styles.css has no content.Bellamy, F. D.; Ou, K. (1984-01-01). "Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium". Tetrahedron Letters. 25 (8): 839–842. doi:10.1016/S0040-4039(01)80041-1. ISSN 0040-4039.
  9. ^ Page Module:Citation/CS1/styles.css has no content.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, 32 (2), Kluwer Academic Publishers: 217–223, doi:10.1023/A:1014725116051, S2CID 54499902
  10. ^ Page Module:Citation/CS1/styles.css has no content.Ellis, Frank (2002). Paracetamol: a curriculum resource. Cambridge: Royal Society of Chemistry. ISBN 0-85404-375-6.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Anthony S. Travis (2007). "Manufacture and uses of the anilines: A vast array of processes and products". In Zvi Rappoport (ed.). The chemistry of Anilines Part 1. Wiley. p. 764. ISBN 978-0-470-87171-3.
  12. ^ Script error: No such module "Template wrapper".
  13. ^ Page Module:Citation/CS1/styles.css has no content.F. B. Dains, Floyd Eberly (1935). "p-Iodophenol". Organic Syntheses. 15: 39. doi:10.15227/orgsyn.015.0039.
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