604-66-0

Usage

Uses

Used in Research Applications:
Diacetic acid 9,10-anthracenediyl ester is used as a fluorescent dye for biological and chemical research, enabling the visualization and tracking of molecules and cellular processes due to its fluorescent properties.
Used in Organic Synthesis:
In the field of organic synthesis, diacetic acid 9,10-anthracenediyl ester is used as a building block for the preparation of other compounds, contributing to the development of new chemical entities and materials.
Safety Precautions:
It is important to handle diacetic acid 9,10-anthracenediyl ester with care, as it may be harmful if ingested or inhaled, and can cause irritation to the skin and eyes. Proper safety precautions and handling procedures should be followed when working with this chemical compound.

InChI:InChI=1/C18H14O4/c1-11(19)21-17-13-7-3-5-9-15(13)18(22-12(2)20)16-10-6-4-8-14(16)17/h3-10H,1-2H3

Upstream product

• 108-24-7 acetic anhydride 
• 76664-78-3 dispiro 
• 127-09-3 sodium acetate 
• 84-65-1 9,10-phenanthrenequinone 
• 113160-87-5 C₂₃H₂₂O₆ 

Downstream Products

• 120-12-7 anthracene 
• 84-65-1 9,10-phenanthrenequinone 
• 38701-90-5 9,10-bis(phenylthio)anthracene 

Relevant academic research and scientific papers

Intermediates in the cleavage of endoperoxides

The decomposition of anthracene endoperoxides has been investigated under various conditions. Thermolyses proceed via radical intermediates and afford anthracenes and rearrangement products, depending on the substitution pattern. Interestingly, not only the O–O but also the C–O bond can be cleaved homolytically. Under basic conditions fragmentations take place, affording anthraquinone, and reactive oxygen species. This mechanism explains the often observed decomposition of endoperoxides during work-up. Finally, an acid-catalyzed cleavage has been observed under release of hydrogen peroxide. The results should be interesting for the mechanistic understanding of peroxide decomposition and the endoperoxides might serve as mild sources of reactive oxygen species for future applications. Copyright

Process for the production of carboxylic acid esters of 9,10-dihydroxy anthracene

In einem Verfahren zur Herstellung von 9,10-Dihydroxyanthracencarbons?ureester und dessen Abk?mmlingen durch katalytische Oxidation von Anthracen wird Anthracen in der flüssigen Phase in einem Carbons?uremedium in Gegenwart eines organischen Metallsalzes und eines Aktivierungsmittels für das Metallsalz bei einer Temperatur von etwa 40 °C und mehr unter Einwirkung von Sauerstoff und Licht behandelt, der Niederschlag abgetrennt, der flüssige Rest mit Veresterungsmitteln behandelt und der erhaltene Ester aus dem Reaktionsgemisch isoliert.

Syntheses and reactions of spirocyclopropaneanthrones. Part 2. Rearrangements and cyclopropyl ring-opening reactions of phenyl-substituted spirocyclopropaneanthrones and related compounds

Diphenylspirocyclopropaneanthrones [(1c) and (1d)] thermally rearranged with ring expansion to 1,10b-dihydro-2H-aceanthrones (2), whereas the phenyl analogue (1b) did not rearrange under comparable conditions. Phenylspirocyclopropeneanthrone (3a), prepared by the carbenic reaction of 10-diazoanthrone (6) with phenylacetylene, thermally rearranged to 10bH-aceanthrone (11). By contrast, the diphenyl analogue (3b), from the reaction with diphenylacetylene, was thermally stable. The diazoketone (6) reacted with 9-methylenefluorene to give directly the rearrangement product (2g), instead of the dispirocyclopropaneanthrone (1g). Spirocyclopropane-and spirocyclopropene-anthrones [(1) and (3)] reacted under acidic conditions to yield cyclopropyl or cyclopropenyl ring-opened products. In these reactions, the ring was shown to open from the more substituted side. These reactions are discussed in mechanistic terms.