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 Edit this at Wikidata
EC Number	204-208-4
KEGG	C14444
PubChem CID	8341
UNII	65Z03V2Z09
CompTox Dashboard (EPA)	DTXSID6020068 Edit this at Wikidata
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	223.231g·mol⁻¹
Appearance	white solid
Melting point	302–303°C (576–577°F; 575–576K)
Hazards
GHS labelling:
Pictograms	GHS08: Health hazard
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], 100kPa). Infobox references

Chemical compound

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]

1 2 3 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.