3-Aminophenol

3-Aminophenol^[1]
Names
	Preferred IUPAC name 3-Aminophenol
	Other names m-Aminophenol (no longer recommended); 3-Hydroxyaniline; m-Hydroxyaniline
Identifiers
CAS Number	591-27-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28924 ;
ChEMBL	ChEMBL269755 ; ChEMBL376136 ;
ChemSpider	11080 ;
ECHA InfoCard	100.008.830
EC Number	209-711-2;
KEGG	C05058 ;
PubChem CID	11568;
UNII	L3WTS6QT82 ;
CompTox Dashboard (EPA)	DTXSID3024497 ;
	InChI InChI=1S/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2 Key: CWLKGDAVCFYWJK-UHFFFAOYSA-N ; InChI=1/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2 Key: CWLKGDAVCFYWJK-UHFFFAOYAM;
	SMILES Oc1cccc(N)c1;
Properties
Chemical formula	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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

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

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

^ 3-Aminophenol at Sigma-Aldrich.
^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ ^a ^b Mitchell, Stephen C.; Waring, Rosemary H. (2000). "Aminophenols". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_099.
^ 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.

[1] 3-Aminophenol at Sigma-Aldrich.

[IUPAC2013_690-2] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[Ullmann-3] 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.

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