2-Aminophenol

Names

Preferred IUPAC name

2-Aminophenol

Other names

o-Aminophenol (no longer recommended)
2-Hydroxyaniline
2-Amino-1-hydroxybenzene

Identifiers

CAS Number

95-55-6^Y

3D model (Jmol)

ChEBI

CHEBI:18112^Y

ChemSpider

5596^Y

DrugBank

DB01726^Y

ECHA InfoCard

100.002.211

KEGG

C01987^Y

UNII

23RH73DZ65^Y

InChI

InChI=1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2^Y

Key: CDAWCLOXVUBKRW-UHFFFAOYSA-N^Y
InChI=1/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2

Key: CDAWCLOXVUBKRW-UHFFFAOYAP

SMILES

Oc1ccccc1N
c1ccc(c(c1)N)O

Properties

Chemical formula

C₆H₇NO

Molar mass

109.13 g/mol

Appearance

White orthorhombic pyramidal needles

Density

1.328 g/cm³

Melting point

174 °C (345 °F; 447 K)

Solubility in water

slightly soluble in cold water, soluble in hot water

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

2-Aminophenol is an organic compound with the formula | C=6 | H=4 (OH)N| H=2 . 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. Reflecting its slight hydrophilic character, white powder is moderately soluble in alcohols and can be recrystallised from hot water.

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.

The compound exhibits intra- and intermolecular hydrogen bond involving the neighbouring amine and hydroxyl groups. As a result, 2-aminophenol has a rather high melting point compared to other compounds with a similar molecular mass such as methylphenol.

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. 2-Aminophenol is an intermediate in the synthesis of dyes. It is particularly useful in yielding 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 useful because they are more stable than their bi- or mono-dentate counterparts.

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Wikipedia