3-Aminophenol

3-Aminophenol^[1]

Names
IUPAC name 3-Aminophenol
Other names m-Aminophenol; 3-Hydroxyaniline; m-Hydroxyaniline
Identifiers
CAS Number	591-27-5
ChEBI	CHEBI:28924
ChEMBL	ChEMBL269755 ChEMBL376136
ChemSpider	11080
EC Number	209-711-2
Jmol interactive 3D	Image
KEGG	C05058
PubChem	11568
UNII	L3WTS6QT82
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/cm^3
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	R20/22 R51/53
S-phrases	S28 S61
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)^[2] or from resorcinol via a substitution reaction with ammonium hydroxide.^[3]

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.^[2]

References

1. 3-Aminophenol at Sigma-Aldrich.
2. Mitchell, Stephen C.; Waring, Rosemary H. (2000). "Aminophenols". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_099.
3. 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.