2294-89-5

Basic information

• Product Name: 9-benzyl-9,10-dihydroanthracene
• Synonyms: 9-benzyl-9,10-dihydroanthracene
• CAS NO: 2294-89-5
• Molecular Weight: 270.374
• Mol File: 2294-89-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 9-benzyl-9,10-dihydroanthracene(CAS DataBase Reference)
• NIST Chemistry Reference: 9-benzyl-9,10-dihydroanthracene(2294-89-5)
• EPA Substance Registry System: 9-benzyl-9,10-dihydroanthracene(2294-89-5)

Safety Data

• Hazardous Substances Data: 2294-89-5(Hazardous Substances Data)

Upstream product

• 90-44-8 anthracen-9(10H)-one 
• 60-29-7 diethyl ether 
• 120-12-7 anthracene 
• 5452-34-6 10,10-dibenzyl-9(10H)-anthracenone 
• 10034-85-2 hydrogen iodide 
• 100-44-7 benzyl chloride 
• 86901-19-1 9,10-dihydro-9,10-anthracendiyl-tris(THF)magnesium 
• 766-04-1 benzyllithium 
• 613-31-0 9,10-dihydroanthracene 
• 50688-77-2 9-benzoyl-9,10-dihydroanthracene 
• 1498-71-1 9-benzylanthracene 
• 67074-07-1 10-Benzyl-9,10-dihydro-[9]anthrol 
• 1564-53-0 9-benzoylanthracene 
• 6921-34-2 benzylmagnesium chloride 

Downstream Products

• 103192-29-6 cis-9-benzyl-10-methyl-9,10-dihydroanthracene 
• 102891-76-9 2-(10-benzyl-9,10-dihydro-[9]anthryl)-2-methyl-propionitrile 

Relevant articles and documents

THE ANIONIC ALKYLATION OF EASILY REDUCIBLE ARENES. A PHOTOCHEMICAL ROUTE TO NUCLEOPHILIC AROMATIC SUBSTITUTION OF ANTHRACENE BY ORGANOLITHIUMS

High yield nuclophilic addition ensues upon mixing tetrahydrofuran solutions of benzyllithium or cyclooctadienyllithium and anthracene at low temperatures.At least part of this addition proceeds by a single electron transfer pathway.Photolysis of the resulting adducts leads to the elimination of lithium hydride, giving net nucleophilic substitution in approximately 50percent yield.The analogous reaction fails with naphthalene, where photolysis of the organolithium/arene mixture leads to dimeric products derived from the organolithium.

Use of Magnesium Anthracene * 3 THF in Synthesis: Generation of Grignard Compounds and Other Reactions with Organic Halides

The course (a), (b), (c) (Scheme 1) of the reaction of magnesium anthracene * 3 THF (1) with organic halides (RX) is dependent on the nature of RX.With alkyl halides in THF 1 reacts as a nucleophile, whereby primary as well as secondary alkyl halides produce dialkyldihydroanthracenes (4-4'') and tertiary alkyl halides yield primarily monoalkyl-substituted dihydroanthracenes (2, 2').With bromo- and iodobenzene in THF 1 reacts predominantly as a radical with H atom abstraction from the solvent affording benzene and 9.The formation of Grignard compounds (5) and anthracene (6), originating from primary and secondary alkyl and aryl halides and 1 in toluene or ether at elevated temperatures, is not caused by the reaction of 1 but by the "active magnesium" (Mg*) formed by decomposition of 1 in these solvents.In contrast, allyl, propargyl, and benzyl halides react with 1 independently of the solvent under mild conditions to produce 5 and 6.Allyl- and the difficultly accessible allenylmagnesium chloride can be prepared in THF at -78 and 0 deg C, respectively, from the corresponding halides and ordinary Mg powder via catalytic amounts of 1.