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

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.

High Intensity, Argon Ion Laser-Jet Photochemistry

A new technique for the study of high intensity solution photochemistry has been developed.With this laser-jet technique, a high velocity microjet is irradiated with the focussed output of an argon ion laser.Under these extremely high intensity conditions, photochemically generated transient species with suitable absorption properties are excited further and produce relatively large amounts of photoproducts which are not observed under low intensity conditions.The application of this laser-jet technique in the study of the photochemistry of radicals, biradicals, photoenols and the higher excited states of carbonyl and polycyclic aromatic compounds is described.

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

Syntheses and Reactions of Spiroanthronetriazolines

Quinone methide 1a reacts with aryl azides 2 to give the corresponding spiroanthronetriazolines 3 along with byproducts, collected in Table I, which are formed by the thermal reaction of 3 or 1a.Quinone methide 1b adds to azides 2 to give spiroanthronetriazolines 5 or their subsequent products.Pyrolysis of 3 regenerates the starting quinone methide 1a and azide 2, and their photolysis leads to 1a.Pyrolysis and photolysis of 5 yield aryliminoanthrone 7, arylaminodibenzocycloheptenone 12, or its isomer 19.Attempts to convert 3 and 5 into spiroanthroneaziridines 14 and 15, respectively, were unsuccessful.Reactions of 3 and 5 with acid catalysts give the rearrangement products dibenzocycloheptenediones 23 and 24, respectively, in high yields.These reactions are discussed in mechanistic terms.