3-Aminophenol

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3-Aminophenol[1]
M-Aminophenol.svg
3-Aminophenol molecule
Names
Preferred IUPAC name
3-Aminophenol
Other names
m-Aminophenol (no longer recommended[2])
3-Hydroxyaniline
m-Hydroxyaniline
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.830
EC Number 209-711-2
KEGG
UNII
Properties
C6H7NO
Molar mass 109.13 g/mol
Appearance White orthorhombic crystals
Density 1.195 g/cm3
Melting point 120 to 124 °C (248 to 255 °F; 393 to 397 K)
Boiling point 164 °C (327 °F; 437 K) at 11 mmHg
Acidity (pKa) 4.17; 9.87
Hazards
R-phrases (outdated) R20/22 R51/53
S-phrases (outdated) S28 S61
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

3-Aminophenol is an organic compound with formula C6H4(NH2)(OH). It is an aromatic amine and aromatic alcohol. It is the meta isomer of 2-aminophenol and 4-aminophenol.

Preparation[edit]

3-Aminophenol can be prepared by caustic fusion of 3-aminobenzenesulfonic acid (i.e. heating with NaOH to 245 °C for 6 hours)[3] or from resorcinol via a substitution reaction with ammonium hydroxide.[4]

Uses[edit]

One of the most relevant applications of the substance is the synthesis of 3-(diethylamino)phenol, key intermediate for the preparation of several fluorescent dyes (e.g., Rhodamine B). Other uses for the compound include hair dye colorants and stabilizers for chlorine-containing thermoplastics.[3]

References[edit]

  1. ^ 3-Aminophenol at Sigma-Aldrich.
  2. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001. Only one name is retained, phenol, for C6H5-OH, both as a preferred name and for general nomenclature. The structure is substitutable at any position. Locants 2, 3, and 4 are recommended, not o, m, and p. 
  3. ^ a b Mitchell, Stephen C.; Waring, Rosemary H. (2000). "Aminophenols". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_099. 
  4. ^ Harada, Haruhisa; Hiroshi, Maki; Sasaki, Shigeru (1986). "Method for the production of m-aminophenol EP0197633A1". Google Patents. Sumitomo Chemical Company, Limited. Retrieved 3 February 2015.