2-Aminophenol

2-Aminophenol
2-Aminophenol
Identifiers
CAS number 95-55-6 YesY
ChemSpider 5596 YesY
UNII 23RH73DZ65 YesY
DrugBank DB01726
KEGG C01987 YesY
ChEBI CHEBI:18112 YesY
ChEMBL CHEMBL28319 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C6H7NO
Molar mass 109.13 g/mol
Appearance White orthorhombic pyramidal needles
Density 1.328 g/cm³
Melting point

174 °C

Solubility in water slightly soluble in cold water, soluble in hot water
 N (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

2-Aminophenol is an organic compound with the formula C6H4(OH)NH2. Along with its isomer 4-aminophenol, it is an amphoteric molecule and a reducing agent. It is a useful reagent for the synthesis of dyes and heterocyclic compounds.[1] Reflecting its slight hydrophilic character, white powder is moderately soluble in alcohols and can be recrystallised from hot water.

Contents

Synthesis

2-Aminophenol (and its isomer, 4-aminophenol) is industrially synthesized by reducing the corresponding nitrophenol by hydrogen in the presence of various catalysts. The nitrophenols can also be reduced with iron.[1]

Structure

The compound contains an internal hydrogen bond between the neighbouring amine and hydroxyl groups that partly co-ordinates with the same groups on a neighbouring molecule as well. As a result, 2-aminophenol has a rather high melting point compared to other molecules with a similar molecular mass such as methylphenol.[2]

Applications

2-Aminophenol has a variety of uses. As a reducing agent, it is marketed under the names of Atomal and Ortol to develop black and white photographs.[1] 2-Aminophenol is an intermediate in the synthesis of dyes. It is particularly useful in yielding tridentate ligands for metal-complex dyes when diazotized and coupled to a phenol, naphthol, or other aromatic or resonant dye species. Metal complex dyes using copper or chromium are commonly used for producing dull colors. Tridentate ligand dyes are particularly useful, since they are more stable than their bi- or mono-dentate counterparts.[3][4]

2-aminophenol diaz coup.png 2-aminophenol coord.png

Due to the adjacency of the amino and hydroxyl groups, 2-aminophenol readily forms heterocycles. These heterocycles, such as benzoxazoles, can be biologically active and useful in the pharmaceutical industry:[1]

2-aminophenol cyclization.png

References

  1. ^ a b c d Mitchell, S.C. & Waring, R.H. “Aminophenols.” In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a02_099.
  2. ^ Reference Handbook of Fine Chemicals, Acros Organics Publishers, Fisher Scientific UK, (2007), www.acros.com
  3. ^ Grychtol, K.; Mennicke, W. “Metal-Complex Dyes.” In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a16_299.
  4. ^ Hunger, K.; Mischke, P.; Rieper, W.; Raue, R.; Kunde, K.; Engel, A. “Azo Dyes.” In Ullmann’s Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, doi:10.1002/14356007.a03_245.

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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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