4-Aminophenol

4-Aminophenol
4-Aminophenol
Identifiers
CAS number 123-30-8 YesY
PubChem 403
ChemSpider 392 YesY
UNII R7P8FRP05V YesY
KEGG C02372 YesY
MeSH Aminophenols
ChEBI CHEBI:17602 YesY
ChEMBL CHEMBL1142 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C6H7NO
Molar mass 109.13 g/mol
Density 1.13 g/cm3
Melting point

188–190 °C

Boiling point

284 °C

Solubility in water 1.5 g/100 ml (25 °C)
Hazards
EU Index 616-003-00-0
EU classification 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
NFPA 704.svg
1
2
0
Flash point 195 °C
Related compounds
Related aminophenols 2-Aminophenol
3-Aminophenol
Related compounds Aniline
Phenol
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

4-Aminophenol is the organic compound with the formula H2NC6H4OH. 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.

Contents

Preparation

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:[2]

C6H5NO2 + 2 H2 → C6H5NHOH + H2O
C6H5NHOH → HOC6H4NH2

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:[3][4][5]

Synthesis of paracetamol from phenol.png

References

  1. ^ CRC Handbook of Chemistry and Physics 65th Ed.
  2. ^ Mitchell, S.C. & Waring, R.H. “Aminophenols.” In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a02_099
  3. ^ Ellis, Frank (2002). Paracetamol: a curriculum resource. Cambridge: Royal Society of Chemistry. ISBN 0-85404-375-6. 
  4. ^ 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. 
  5. ^ 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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Look at other dictionaries:

  • aminophenol — [ə mē΄nōfē′nōl, am΄ə nō΄fē′nōl, ə ē΄nō fē′nôl΄, am΄ə nō΄fē′näl΄] n. any of several white or light red crystalline compounds, NH2C6H4OH (esp. para aminophenol), used in making dyes and as a photographic developer …   English World dictionary

  • aminophénol — ● aminophénol nom masculin Composé renfermant une ou plusieurs fonctions amines et une ou plusieurs fonctions phénols. (Parmi les trois isomères de formule H2N―C6H4―OH, l isomère méta sert à la fabrication des rhodamines, l isomère ortho à la… …   Encyclopédie Universelle

  • Aminophenol — Aminophenole Name o Aminophenol m Aminophenol p Aminophenol Andere Namen 2 Aminophenol, 2 Hydroxyanilin 3 Aminophenol, 3 Hydroxyanilin 4 Aminophenol, 4 Hydroxyanilin Strukturformel …   Deutsch Wikipedia

  • Aminophenol — chembox new ImageFileL1 = 4 Aminophenol.svg ImageSizeL1 = 80px ImageFileR1 = 4 Aminophenol3d.png IUPACName = 4 Aminophenol OtherNames = Formula = C6H7NO Section1 = Chembox Identifiers Abbreviations = CASNo = 123 30 8 EINECS = SMILES = InChI =… …   Wikipedia

  • aminophenol — ˈ ̷ ̷ˌ ̷ ̷ noun ( s) Etymology: International Scientific Vocabulary amin + phenol; originally formed in German 1. : any of three crystalline compounds NH2C6H4OH derived from phenol, distinguished as ortho aminophenol, meta aminophenol, and …   Useful english dictionary

  • aminophenol — /euh mee noh fee nawl, nol, am euh noh /, n. Chem. a white crystalline substance, C6H7NO, occurring in three isomers, meta , ortho , and para aminophenol: used as an intermediate for dyes and as a photographic developer. [AMINO + PHENOL] * * * …   Universalium

  • aminophenol — aminofenolis statusas T sritis chemija formulė C₆H₄(NH₂)OH atitikmenys: angl. aminophenol rus. аминофенол …   Chemijos terminų aiškinamasis žodynas

  • aminophenol — noun Any of three isomeric amino derivatives of phenol …   Wiktionary

  • Aminophenol — Ami|no|phe|nol 〈n. 11; Chem.〉 Derivat des Phenols, bei dem Wasserstoff durch die Aminogruppe ersetzt wird; oV Amidophenol * * * A|mi|no|phe|nol; unsystematisches Syn.: Hydroxyanilin: H2N C6H4 OH; farblose, autoxidable, hautreizende krist. Verb.… …   Universal-Lexikon

  • Aminophenol — A|mi|no|phe|nol 〈n.; Gen.: s; Pl.: unz.; Chemie〉 Derivat des Phenols, bei dem Wasserstoff durch die Aminogruppe ersetzt wird; Syn. Amidophenol …   Lexikalische Deutsches Wörterbuch

  • aminophenol — n. crystalline phenol compound used in photography and the production of dyes (Chemistry) …   English contemporary dictionary

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