Synthesis of 9,10-phenanthrenequinone

Preparation of 9,10-phenanthrenequinone

Alternative Names: Phenanthrene-9,10-dione; Phenanthrenequinone; 9,10-Phenanthraquinone; 84-11-7; Phenanthraquinone;

Preparation of 9,10-phenanthrenequinone

Preparation of 9,10-phenanthrenequinone

30 g phenanthrene are dissolved in the heat in 120 g acetic acid, and a solution of 70 g chromic acid in about 200 g strong acetic acid is gradually added. This latter solution is prepared by dissolving the chromic acid in a very little water, and then pouring the aqueous solution into glacial acetic acid. The mixture gets warm spontaneously, and it is easy so to carry out the operation that the temperature remains approximately at the boiling point of the acetic acid. Finally most of the acetic acid is distilled off and the residue is then treated with water. The reddishyellow crystalline mass precipitated, which contains the 9,10-phenanthrenequinone along with some unchanged phenanthrene, is filtered and washed with a little hot water. To purify the crude 9,10-phenanthrenequinone it is treated in the warm with a dilute solution of sodium bisulfite; the filtrate is warmed on the water-bath, and the 9,10-phenanthrenequinone precipitated by acidifying with sulfuric acid. This product is then recrystallized from a large quantity of boiling alcohol.

Introduction to the preparation of organic compounds, E. Fisher, 121-122, 1909

IUPAC Name

phenanthrene-9,10-dione

InChI

InChI=1S/C14H8O2/c15-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(13)16/h1-8H

InChI Key

YYVYAPXYZVYDHN-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)C3=CC=CC=C3C(=O)C2=O

MeSH Synonyms

9,10-phenanthraquinone, 9,10-phenanthrenedione, 9,10-phenanthrenequinone, 9,10-phenanthroquinone

Depositor-Supplied Synonyms

9,10-Phenanthrenequinone, Phenanthrene-9,10-dione, Phenanthrenequinone, 9,10-Phenanthraquinone, 84-11-7, Phenanthraquinone, 9,10-PHENANTHRENEDIONE, 9,10-Phenanthroquinone, phenanthrene-9,10-quinone, 9-10 Phenanthrene quinone, CHEMBL51931, UNII-42L7BZ8H74, MLS000881132, Phenanthrene, 9,10-dihydro-9,10-dioxo-, CCRIS 7615, CHEBI:37454, HSDB 4489, YYVYAPXYZVYDHN-UHFFFAOYSA-N, EINECS 201-515-5, NSC 10446, 9,10-dihydrophenanthrene-9,10-dione, BRN 0608838, SMR000150826, AI3-23739, WLN: L B666 HVVJ, Phenanthrene,10-dihydro-9,10-dioxo-, Phenanthroquinone, Phenanthrene chinone, Phenanthrene-9,10 dione, cid_6763, SCHEMBL43050, KSC908S3D, MLS000571180, ACMC-20977q, 156507_ALDRICH, 275034_ALDRICH, AC1L1N91, BDBM22857, CTK8A8931, NSC7389, 1,2-Dione-Based Compound, 14, MolPort-000-639-548, 42L7BZ8H74, HMS2231F24, KUC103886N, EBD42196, NSC-7389, NSC10446, ANW-13620, CX1139, DNC007853, KSC-1-127, NSC-10446, SBB058783, STK793149, ZINC01529614, AKOS000120609, MCULE-9308842057, RP26413, RTR-026056, NCGC00246089-01, AJ-26620, AK-96664, AN-10590, BP-13416, K501, KB-79910, PL000117, SC-17706, DB-005403, LS-102685, ST2413662, ST4022387, TR-026056, P0080, P1136, A-8615, C03243, 4-07-00-02565 (Beilstein Handbook Reference), A840718, AF-936/31262009, CS-006/03886049, SR-01000512656, I14-0889, SR-01000512656-4, T0519-8206, A1027/0048111

Removed Synonyms

CID6763, c0511, C005399

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *