1,10-Phenanthroline-5,6-dione

1,10-Phenanthroline-5,6-dione
Identifiers
CAS Number	27318-90-7 [ChemSpider];
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:231244;
ChEMBL	ChEMBL235504;
ChemSpider	65646;
ECHA InfoCard	100.156.024
EC Number	627-684-9;
IUPHAR/BPS	11323;
PubChem CID	72810;
UNII	8JD7KXA2W0;
CompTox Dashboard (EPA)	DTXSID60181763 ;
	InChI InChI=1S/C12H6N2O2/c15-11-7-3-1-5-13-9(7)10-8(12(11)16)4-2-6-14-10/h1-6H Key: KCALAFIVPCAXJI-UHFFFAOYSA-N;
	SMILES C1=CC2=C(C3=C(C=CC=N3)C(=O)C2=O)N=C1;
Properties
Chemical formula	C12H6N2O2
Molar mass	210.192 g·mol−1
Appearance	orange solid
Melting point	260 °C (500 °F; 533 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,10-Phenanthroline-5,6-dione is an organic compound with the formula C₁₂H₆O₂N₂. It is the quinone derivative of 1,10-phenanthroline. The compound exhibits many reactions, including condensations with diamines to give quinoxalines and decarbonylation to give a diazafluorenone.^[1]

The compound is prepared by oxidation of 1,10-phenanthroline with a mixture of nitric and sulfuric acids.^[1] 5-Nitro-1,10-phenanthroline is an intermediate.^[2]

References

^ ^a ^b Dickeson, JE; Summers, LA (1970). "Derivatives of 1,10-Phenanthroline-5,6-quinone". Australian Journal of Chemistry. 23 (5): 1023. doi:10.1071/ch9701023.
^ Smith, G. Frederick; Cagle, F. Wm. (1947). "The Improved Synthesis of 5-Nitro-1, 10-Phenanthroline". The Journal of Organic Chemistry. 12 (6): 781–784. doi:10.1021/jo01170a007. PMID 18919731.

[AJC-1] Dickeson, JE; Summers, LA (1970). "Derivatives of 1,10-Phenanthroline-5,6-quinone". Australian Journal of Chemistry. 23 (5): 1023. doi:10.1071/ch9701023.

[2] Smith, G. Frederick; Cagle, F. Wm. (1947). "The Improved Synthesis of 5-Nitro-1, 10-Phenanthroline". The Journal of Organic Chemistry. 12 (6): 781–784. doi:10.1021/jo01170a007. PMID 18919731.

[1]

[2]

See also

References