3-Aminophenol

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

3-Aminophenol^[1]

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 Y
3D model (JSmol)	Interactive image
Beilstein Reference	636059
ChEBI	CHEBI:28924 Y
ChEMBL	ChEMBL269755 Y ChEMBL376136 Y
ChemSpider	11080 Y
ECHA InfoCard	100.008.830
EC Number	209-711-2
Gmelin Reference	2913
KEGG	C05058 Y
PubChem CID	11568
RTECS number	SJ4900000
UNII	L3WTS6QT82 Y
UN number	2512
CompTox Dashboard (EPA)	DTXSID3024497
InChI InChI=1S/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2 Y Key: CWLKGDAVCFYWJK-UHFFFAOYSA-N Y 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 labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H332, H411
Precautionary statements	P261, P264, P270, P271, P273, P301+P312, P304+P312, P304+P340, P312, P330, P391, P501
NFPA 704 (fire diamond)	2 0 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Preparation

3-Aminophenol is prepared by reduction of 3-nitrophenol. It can also 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, which is used 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]