Surf Wiki
Save to docs
general/aminophenols

From Surf Wiki (app.surf) — the open knowledge base

4-Aminophenol

| p-Aminophenol | para-Aminophenol | 5.48 (amino; H2O) | 10.30 (phenol; H2O) |NFPA-H = 2 |NFPA-F = 1 |NFPA-R = 0 |NFPA-S = - 3-Aminophenol Phenol 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 and anticonvulsant effects..

Commercially available as a white powder, 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.

TOC

Preparation

4-Aminophenol can be prepared by several routes. One route is hydrogenation of 4-nitrophenol over Raney nickel. :HOC6H4NO2 + 3 H2 → HOC6H4NH2 + 2 H2O The nitrophenol can also be reduced by iron or by stannous chloride.

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

It is a precursor to amodiaquine, mesalazine, AM404, parapropamol, B-86810 & B-87836 (cf. ).

4-Aminophenol converts readily to the diazonium salt.

References

References

  1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. (2016). "CRC Handbook of Chemistry and Physics". [[CRC Press]].
  3. (February 2006). "The analgesic activity of paracetamol is prevented by the blockade of cannabinoid CB1 receptors". European Journal of Pharmacology.
  4. (January 2011). "Acetaminophen inhibits status epilepticus in cultured hippocampal neurons". NeuroReport.
  5. [[CRC Handbook of Chemistry and Physics]] 65th Ed.
  6. (2000). "Ullmann's Encyclopedia of Industrial Chemistry".
  7. "Process of preparing nu-acetyl-p-amino phenol".
  8. (1984-01-01). "Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium". Tetrahedron Letters.
  9. (2002). "Electroreduction of nitrobenzene to p-aminophenol using voltammetric and semipilot scale preparative electrolysis techniques". Kluwer Academic Publishers.
  10. Ellis, Frank. (2002). "Paracetamol: a curriculum resource". Royal Society of Chemistry.
  11. Anthony S. Travis. (2007). "The chemistry of Anilines Part 1". Wiley.
  12. Elmar Friderichs. "Analgesics and Antipyretics".
  13. F. B. Dains, Floyd Eberly. (1935). "p-Iodophenol". Organic Syntheses.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

aminophenols human-drug-metabolites
Want to explore this topic further?

Ask Mako anything about 4-Aminophenol — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report