Wikipedia

1,10-Phenanthroline-5,6-dione

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]

1,10-Phenanthroline-5,6-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.156.024 Edit this at Wikidata
EC Number
  • 627-684-9
UNII
  • 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
  • C1=CC2=C(C3=C(C=CC=N3)C(=O)C2=O)N=C1
Properties
C12H6N2O2
Molar mass 210.192 g·mol−1
Appearance orange solid
Melting point 260 °C (500 °F; 533 K)
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
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).

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]

See also

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References

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  1. ^ 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.
  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.
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