10210-34-1

Upstream product

• 784-04-3 9-acetylanthracene 
• 7396-21-6 1-acetylanthracene 
• 120-12-7 anthracene 
• 75-36-5 acetyl chloride 

Downstream Products

• 78080-80-5 1,5-Bis-phenylethynyl-anthracene 
• 78053-72-2 1,5-Bis-phenylethynyl-anthraquinone 
• 41694-83-1 anthracene-1,5-dicarboxylic acid 
• 10210-32-9 2-acetylanthracene 
• 53307-88-3 3-methylbenz[de]anthracen-1-one 
• 10208-16-9 1,8-diacetylanthracene 

Relevant academic research and scientific papers

Reversible Friedel-Crafts acylations of anthracene: Rearrangements of acetylanthracenes

Treatment of 1-acetylanthracene (1-AcAN) and 9-acetylanthracene (9-AcAN) with PPA at 80-120 °C leads to the nearly complete conversion of these isomers into 2-acetylanthracene (2-AcAN), an illustration of the Agranat-Gore rearrangement of polycyclic aromatic ketones (PAKs). Ab initio MP2/6-31(d) calculations predict the following order of stabilities: for O-complexes: 9-AcAN>1-AcAN>2-AcAN; for ketones: 2-AcAN>1-AcAN>9-AcAN; for O-protonated ketones: 2-AcAN>1-AcAN>9-AcAN. Thus, 9-AcAN is the kinetically controlled product, whereas 2-AcAN is the thermodynamically controlled product. No reverse rearrangements of 2-AcAN to either 9-AcAN or 1-AcAN and of 1-AcAN to 9-AcAN were observed. The results strengthen the pattern of reversibility in Friedel-Crafts acylations of PAHs.

Friedel-Crafts reactions in room temperature ionic liquids

Friedel-Crafts reactions in the ionic liquid system 1-methyl-3-ethylimidazolium chloride-aluminium(III) chloride can be performed with excellent yields and selectivities, and in the case of anthracene, have been found to be reversible.