4159-04-0

Basic information

• Product Name: 10-Methyleneanthracen-9(10H)-one
• Synonyms: 10-Methyleneanthracen-9(10H)-one;Anthraquinonemethide
• CAS NO: 4159-04-0
• Molecular Formula: C₁₅H₁₀O
• Molecular Weight: 0
• Mol File: 4159-04-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 10-Methyleneanthracen-9(10H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Methyleneanthracen-9(10H)-one(4159-04-0)
• EPA Substance Registry System: 10-Methyleneanthracen-9(10H)-one(4159-04-0)

Safety Data

• Hazardous Substances Data: 4159-04-0(Hazardous Substances Data)

Upstream product

• 779-02-2 9-methylanthracene 
• 127-09-3 sodium acetate 
• 19399-56-5 2',2'-diphenylspiro-10-one 
• 73079-02-4 C₂₁H₁₄N₄O₃ 
• 33739-69-4 9-methyl-10-hydro-9,10-epidioxyanthracene 

Downstream Products

• 18792-80-8 1-phenylbenzanthrone 
• 82-05-3 7H-benz[d,e]anthracene-7-one 
• 13668-04-7 2,3-diphenyl-7H-benzo[de]anthracen-7-one 
• 6535-66-6 3-benzoyl-benz[de]anthracen-7-one 
• 58255-90-6 10-benzyl-10-hydroperoxy-anthrone 
• 16603-23-9 10-benzyl-9(10H)-anthracenone 
• 5737-94-0 dibenzoperylene-8,16-dione 
• 857580-26-8 2,3-dibenzoyl-benz[de]anthracen-7-one 
• 116-96-1 13,13'-dibenzanthronyl 
• 100770-94-3 anthrol bue 
• 19399-56-5 2',2'-diphenylspiro-10-one 
• 73079-07-9 10-(4-chlorophenylimino)anthrone 
• 73079-00-2 C₂₁H₁₄ClN₃O 
• 73079-14-8 C₂₈H₂₀Cl₂N₂O 

Relevant articles and documents

Interaction of 9-substituted anthracenes with oxidation systems tert-butylhydroperoxide-metal tert-butoxide

9-R-Anthracenes (R = Me, Ph) are effective acceptors of peroxyl and metalalkoxyl radicals in the systems tert-butylhydroperoxide-metal tert-butoxide (M = Al, V, Cr; C6H6, 20°C). Isolation of 9-R-9,10-dihydro-9,10-di-tert-butylperoxyanthracenes, 10-R-10-tert-butylperoxy-9-anthrones as major products reliably confirms the formation of tert-butylperoxy radicals and can be used for quantitative assessment of their content.

Products and Mechanism of the Oxidation of 9-Methylanthracene by Peroxydisulfate. Proton Loss and Nucleophile Addition Reactions of the 9-Methylanthracene Radical Cation

The Cu(II)-S2O82- oxidation of 9-methylanthracene (1) was studied in refluxing CH3CN/acetic acid and aqueous CH3CN.Side-chain and nuclear oxidation products and the dimeric compound lepidopterene (7) were produced.The lepidopterene was determined to be formed by the reaction of intermediate anthracenylmethyl cation with 1.In CH3CN/H2O nuclear oxidation products, 10-hydroxy-10-methyl-9-anthrone (2) and 10-methylene-9-anthrone (3) and dimer 7 were produced, with the nuclear products predominating.In CH3CN/HOAc the dimer and side-chain substitution products, 1-OAc (5a) and 1-NHAc (5c), were predominant over the nuclear products, which consisted mainly of 3 and 10-acetoxy-9-methylanthracene (4a).A mechanism is proposed where the initially formed radical cation undergoes competing proton loss and reversible nucleophile addition reactions to form respectively the anthracenylmethyl radical and nucleophile adduct radicals.Oxidation of the radicals by Cu(II) or S2O82- yield the corresponding cations that react to form the products 4,5, and 7.Compounds 2 and 3 form by subsequent oxidation of the nuclear oxidation product, 10-methyl-9-anthrol.The results suggest that nucleophile addition is faster than proton loss and that it is more reversible in CH3CN/HOAc than in CH3CN/H2O