3-Aminophenol

3-Aminophenol[1]
	3-Aminophenol molecule
Names
	Preferred IUPAC name 3-Aminophenol[2]
	Other names m-Aminophenol; meta-Aminophenol; 3-Hydroxyaniline; m-Hydroxyaniline; meta-Hydroxyaniline
Identifiers
CAS Number	591-27-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	636059
ChEBI	CHEBI:28924 ;
ChEMBL	ChEMBL269755 ; ChEMBL376136 ;
ChemSpider	11080 ;
ECHA InfoCard	100.008.830
EC Number	209-711-2;
Gmelin Reference	2913
KEGG	C05058 ;
PubChem CID	11568;
RTECS number	SJ4900000;
UNII	L3WTS6QT82 ;
UN number	2512
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	109.128 g·mol−1
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)	4.37 (amino; 20 °C, H2O); 9.82 (phenol; 20 °C, H2O)[3];
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H302, H332, H411
GHS precautionary statements	P261, P264, P270, P271, P273, P301+312, P304+312, P304+340, P312, P330, P391, P501
NFPA 704 (fire diamond)	0 2 0
	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

3-Aminophenol can be prepared by caustic fusion of 3-aminobenzenesulfonic acid (i.e. heating with NaOH to 245 °C for 6 hours)[4] or from resorcinol via a substitution reaction with ammonium hydroxide.[5]

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.[4]

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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. 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.
Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
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.

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[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. 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.

[CRC97-3] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.

[Ullmann-4] Mitchell, Stephen C.; Waring, Rosemary H. (2000). "Aminophenols". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_099.

[5] 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.