Description

1,10-Phenanthroline-5,6-dione (CAS No. 27318-90-7) is a high-purity, heterocyclic organic compound with the molecular formula C₁₂H₆N₂O₂. This quinone derivative of 1,10-phenanthroline is a versatile building block in coordination chemistry and materials science, prized for its redox-active properties and ability to form stable metal complexes. The bright yellow crystalline powder exhibits excellent solubility in polar organic solvents such as DMSO and DMF, making it ideal for solution-phase synthesis. With a purity of ≥98% (HPLC), this reagent is rigorously tested by QC to ensure batch-to-batch consistency for sensitive applications. Suitable for use as a ligand in catalytic systems, electrochemical sensors, and molecular electronics research. Packaged under inert gas in amber glass vials to prevent degradation, with optional argon-sealed ampules available for oxygen-sensitive work.

Properties

• CAS Number: 27318-90-7
• Complexity: 297
• IUPAC Name: 1,10-phenanthroline-5,6-dione
• 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
• InChI Key: KCALAFIVPCAXJI-UHFFFAOYSA-N
• Exact Mass: 210.042927438
• Molecular Formula: C12H6N2O2
• Molecular Weight: 210.19
• SMILES: C1=CC2=C(C3=C(C=CC=N3)C(=O)C2=O)N=C1
• Topological: 59.9
• Monoisotopic Mass: 210.042927438
• Synonyms: 1,10-Phenanthroline-5,6-dione, 27318-90-7, LDN-73794, phendione, 8JD7KXA2W0, 1,10-Pad, 1,10-phenanthroline-5,6-quinone, 1,10-phenanthrolinequinone, NSC 346882, NSC-346882, BCMH 1-48, 5,6-dioxo-1,10-phenanthroline, DTXSID60181763, 1,10-PHENANTHROLIN-5,6-DIONE, phen-dione, DTXCID00104254, 627-684-9, inchi=1/c12h6n2o2/c15-11-7-3-1-5-13-9(7)10-8(12(11)16)4-2-6-14-10/h1-6, MFCD00014473, 1 10-PHENANTHROLINE-5 6-DIONE 97, MLS003171048, T5-8, 5,6-dihydro-1,10-phenanthroline-5,6-dione, pyridino[3,2-h]quinoline-5,6-dione, [1,10]Phenanthroline-5,6-dione, 1 10-PHENANTHROLINE-5 6-DIONE, Stahl phd oxidant, NSC346882, UNII-8JD7KXA2W0, cid_72810, SCHEMBL460433, CHEMBL235504, BDBM22860, GTPL11323, 1,2-Dione-Based Compound, 17, CHEBI:231244, GLXC-01827, BCP22583, CS-D0379, SBB002415, STK681092, AKOS005068282, AC-7578, FP60900, GS-4495, 1,10-Phenanthroline-5,6-dione, 97%, SMR001874957, ST078868, SY019736, DB-005603, 5,6-dihydro-1=10-phenantroline-5,6-dione, P1973, SR-01000899541, SR-01000899541-2, [1,10]Phenanthroline-5,6-dione ; 1,10-Phenanthroline-5,6-quinone, [1,10]Phenanthroline-5,6-dione;1,10-Phenanthroline-5,6-quinone

Application

1,10-Phenanthroline-5,6-dione serves as a key precursor for synthesizing redox-active transition metal complexes in electrocatalysis research. The compound’s orthogonal carbonyl groups enable facile modification for creating tailored ligands in supramolecular chemistry. Researchers utilize it as an electron-accepting moiety in the development of organic semiconductors and photovoltaic materials. Its chelating properties make it valuable in constructing luminescent probes for metal ion detection.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (98.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

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, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (98.8%)

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