546-24-7

Basic information

• Product Name: 8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-one
• Synonyms: 8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-one
• CAS NO: 546-24-7
• Molecular Formula: C₁₄H₁₄O₂
• Molecular Weight: 214.263
• Mol File: 546-24-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 296.9 °C at 760 mmHg
• Flash Point: 123.4 °C
• Appearance: /
• Density: 1.174 g/cm³
• Vapor Pressure: 0.00139mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: 8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-one(546-24-7)
• EPA Substance Registry System: 8,9b-dimethyl-4,4a-dihydrodibenzofuran-3-one(546-24-7)

Safety Data

• Hazardous Substances Data: 546-24-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 309, 1972 DOI: 10.1021/ja00756a071

InChI:InChI=1/C14H14O2/c1-9-3-4-12-11(7-9)14(2)6-5-10(15)8-13(14)16-12/h3-7,13H,8H2,1-2H3

Upstream product

• 106-44-5 p-cresol 
• 31704-63-9 1-((4aS,9bS)-8,9b-Dimethyl-4a,9b-dihydro-dibenzofuran-3-yl)-pyrrolidine 
• 586-96-9 Nitrosobenzene 
• 119-61-9 benzophenone 
• 65109-76-4 N-p-toluenesulfonyl-O-(4-tolyl)-hydroxylamine 
• 75-91-2 tert.-butylhydroperoxide 
• 6933-26-2 (5-ethyl-2-thienyl)phenylmethanone 

Downstream Products

• 102316-43-8 (+/-)-8,9b-dimethyl-(4ar,9bc)-4a,9b-dihydro-4H-dibenzofuran-3-one-phenylhydrazone 
• 109937-50-0 (+/-)-8,9b-dimethyl-(4ar,9bc)-4a,9b-dihydro-4H-dibenzofuran-3-one-(2,4-dinitro-phenylhydrazone) 
• 78815-92-6 (1S,4aR,9bR)-8,9b-Dimethyl-1-phenyl-1,4,4a,9b-tetrahydro-2H-dibenzofuran-3-one 
• 86657-78-5 (4aS,9bR)-4-[1-Dimethylamino-meth-(E)-ylidene]-8,9b-dimethyl-4a,9b-dihydro-4H-dibenzofuran-3-one 
• 78815-95-9 2-[4-Methyl-2-(1-methyl-4-oxo-cyclohexa-2,5-dienyl)-phenoxy]-acetamide 

Relevant articles and documents

Efficient oxidative ipso-fluorination of para-substituted phenols using pyridinium polyhydrogen fluoride in combination with hypervalent iodine(III) reagents

Diacetoxyiodobenzene (PIDA) and bis(trifluoroacetoxy)iodobenzene (PIFA) in the presence of pyridinium polyhydrogen fluoride (PPHF) are effective for the fluorination of para-substituted phenols to give a variety of 4-fluorocyclohexa-2,5-dienones in a good yield. (R,S)-1,1′-Bi-5,6,7,8- tetrahydro-2-naphthol (and its monoacetate) yields atropoisomeric fluorocyclohexadienones. The 4-substituted carbamate open-chain phenols were readily converted to fluorohydroindolenone and fluorohydroquinolenone derivatives by intramolecular conjugate addition.

The NO3 radical-mediated liquid phase nitration of phenols with nitrogen dioxide

Analysis of Kyodai nitration, which refers to the mixture of NO2 and O3 in nonprotic solvents, may contribute to an understanding of the atmosphere because it can be used in the study of the nitration of aromatic compounds with NOsu

Ingold-Fischer "Persistent Radical Effect", Solvent Effect, and Metal Salt Oxidation of Carbon-Centered Radicals in the Synthesis of Mixed Peroxides from tert-Butyl Hydroperoxide

Mixed peroxides are formed from tert-butyl hydroperoxide (TBH), tert-butyl peroxalate (TBP), and a variety of substrates (p-cresol, cyclohexene, styrene, α-methylstyrene, acrylonitrile, 2-methylcyclohexanone). Also, the oxidation of THF in the presence of acrylonitrile under the same conditions gives the mixed peroxide, generated by addition of the tetrahydrofuranyl radical to the double bond and the cross-coupling of the radical adduct with the tert-butylperoxyl radical. Similarly, benzoyl peroxide, TBH, and acrylonitrile give the mixed peroxide by oxidative arylation of the double bond. Paradoxically, TBH acts as effective inhibitor of the polymerization of vinyl monomers (acrylonitrile, styrene). An overall kinetic evaluation suggests that the conditions for the Ingold-Fischer "persistent radical effect", characterized by the simultaneous formation of a persistent and a transient radical, are fulfilled in all cases. The reactions are strongly affected by solvents, which form hydrogen bonds with TBH. Catalytic amounts of Cu(II) and Fe(III) salts influence the selectivity; the possibility that the mixed peroxides can also be generated by metal salt oxidation of carbon-centered radicals is discussed.