2-Aminoanthraquinone

2-Aminoanthraquinone
Identifiers
CAS Number	17-79-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34258;
ChEMBL	ChEMBL84685;
ChemSpider	8038;
ECHA InfoCard	100.003.827
EC Number	204-208-4;
KEGG	C14444;
PubChem CID	8341;
UNII	65Z03V2Z09;
CompTox Dashboard (EPA)	DTXSID6020068 ;
	InChI InChI=1S/C14H9NO2/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7H,15H2 Key: XOGPDSATLSAZEK-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C=C(C=C3)N;
Properties
Chemical formula	C14H9NO2
Molar mass	223.231 g·mol−1
Appearance	white solid
Melting point	302–303 °C (576–577 °F; 575–576 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H351
Precautionary statements	P203, P280, P318, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Aminoanthraquinone is an organic compound with the formula C₁₄H₉O₂N. It is one of two of monoaminoanthraquinone isomers. The compound is prepared from 2-chloroanthraquinone by treatment with ammonia. A number of other routes have been described, e.g. using nitrobenzene in the diacylation.^[1]

The compound exhibits extensive reactivity, e.g. diazotization.^[1]

It is a precursor to indanthrone, a commercial blue dye.^[2]

Safety

Like many aromatic amines, the potential carcinogenicity of 2-aminoanthraquinone has been scrutinized.^[1]

^ ^a ^b ^c Gouda, M. A.; Berghot, M. A.; Shoeip, A.; Elattar, K. M.; Khalil, A. E.-G. M. (2010). "Chemistry of 2-Aminoanthraquinones". Turkish Journal of Chemistry. doi:10.3906/kim-0912-333.
^ Bien, Hans-Samuel; Stawitz, Josef; Wunderlich, Klaus (2000). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_355. ISBN 3527306730.