32999-99-8

Basic information

• Product Name: 5,5-dimethyl-cyclohexane-1,2,3-trione
• Synonyms: 5,5-dimethyl-cyclohexane-1,2,3-trione
• CAS NO: 32999-99-8
• Molecular Weight: 154.166
• Mol File: 32999-99-8.mol

Chemical Properties

• CAS DataBase Reference: 5,5-dimethyl-cyclohexane-1,2,3-trione(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dimethyl-cyclohexane-1,2,3-trione(32999-99-8)
• EPA Substance Registry System: 5,5-dimethyl-cyclohexane-1,2,3-trione(32999-99-8)

Safety Data

• Hazardous Substances Data: 32999-99-8(Hazardous Substances Data)

Upstream product

• 33932-89-7 2-dimethylsulfuranylidene-5,5-dimethylcyclohexane-1,3-dione 
• 35024-12-5 (4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine 
• 126-81-8 dimedone 

Downstream Products

• 374752-67-7 Ethyl-[2-diazo-2-(1-hydroxy-4,4-dimethyl-2,6-dioxocyclohexyl)acetat] 
• 374752-69-9 Benzyl-[2-diazo-2-(1-hydroxy-4,4-dimethyl-2,6-dioxocyclohexyl)acetat] 
• 70990-64-6 2,3-Dihydroxy-5,5-dimethyl-2-cyclohexen-1-on 
• 725269-60-3 2-Hydroxy-5,5-dimethyl-2-(2-morpholino-2-phenylethenyl)cyclohexan-1,3-dion 
• 725269-61-4 8-Hydroxy-3,3,10,10-tetramethyl-15-morpholino-15-phenyl-7,16,17-trioxapentacyclo[11.3.1.0^1,6.0^6,14.0^8,13]heptadecan-5,12-dion 
• 374752-74-6 Benzyl-(2-hydroxy-5,5-dimethyl-3,7-dioxocyclohept-1-en-1-carboxylat) 
• 28312-42-7 5,5-Dimethyl-3-oxocyclohex-1-en-1-carbonsaeure 

Relevant articles and documents

Facile synthesis of 1,2,3-tricarbonyls from 1,3-dicarbonyls mediated by cerium(IV) ammonium nitrate

A mild and efficient protocol for the synthesis of vicinal tricarbonyl compounds from β-dicarbonyls in a single step using cerium(IV) ammonium nitrate as a catalytic oxidant is described. Ease of execution, wide substrate scope and the suitability for the synthesis of commercially important compounds like ninhydrin, alloxan and oxoline make this reaction particularly noteworthy.

Chemistry of Free Cyclic Vicinal Tricarbonyl Compounds ('1,2,3-Triones'). Part 3. Polar and Redox Reactions of 1,2,3-Triones with Enamines of Different Types - News on Oxonol Dyes, Radicals, and Biradicals

The central C=O groups of cyclic 1,2,3-triones possess outstanding electrophilic (electron-pair-accepting) as well as oxidizing (one-electron-accepting) properties. Thus, 1,2,3-triones are chemically related to 1,2- and 1,4-benzoquinones. Whereas polar reactions with carbanion-like (electron rich) species give rise to nucleophilic addition reactions to C=O groups under exclusive C,C-bond formation, SET (single-electron transfer) or redox reactions effect a partial 'carbonyl Umpolung' via ketyl intermediates (C,C- and/or C,O-bond formation). Here, we report on numerous reactions between electron-rich, more- or less-polar enamines with 5,5-dimethylcyclohexane-1,2,3-trione (9a) and 1H-indene-1,2,3-trione (9b). Various new derivatives of basic oxonol dyes were formed, including the first oxonol dye incorporating a 1,3-dioxocyclohexyl moiety. A novel stable radical, 50/50′, was obtained from 9b and lla via addition, hydrolysis, and treatment with conc. H2SO4. Radical 50/50′ represents a vinylogous 'monodehydroreductone' and is, thus, related to monodehydroascorbic acid (143), to Russell's radical cation (144), to indigo (141/141′), and to quinhydrone.

Introduction of Oxygen Functions into the α-Position of β-Diketones, 8. Ozonolysis of Sulfonium Ylides

(Dimethylsulfonio)diacylmethanides 1, prepared by known methods, are cleaved by equimolar amounts of ozone in aprotic medium yielding vicinal triketones 2 and DMSO.Peroxydic reaction products are not detectable.