1129-21-1

Basic information

• Product Name: 3,5-Cyclohexadiene-1,2-dione, 4-(1,1-dimethylethyl)-
• Synonyms: 3,5-Cyclohexadiene-1,2-dione, 4-(1,1-dimethylethyl)-
• CAS NO: 1129-21-1
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 0
• Mol File: 1129-21-1.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 250.2°C at 760 mmHg
• Flash Point: 94.7°C
• Appearance: /
• Density: 1.092g/cm³
• Vapor Pressure: 0.0219mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: 3,5-Cyclohexadiene-1,2-dione, 4-(1,1-dimethylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Cyclohexadiene-1,2-dione, 4-(1,1-dimethylethyl)-(1129-21-1)
• EPA Substance Registry System: 3,5-Cyclohexadiene-1,2-dione, 4-(1,1-dimethylethyl)-(1129-21-1)

Safety Data

• Hazardous Substances Data: 1129-21-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 4764, 1983 DOI: 10.1021/jo00172a059Synthesis, p. 641, 1985Tetrahedron Letters, 29, p. 677, 1988 DOI: 10.1016/S0040-4039(00)80182-3

InChI:InChI=1/C10H12O2/c1-10(2,3)7-4-5-8(11)9(12)6-7/h4-6H,1-3H3

Upstream product

• 110851-17-7 5-tert-Butyl-2,9,11,12,13-pentaoxa-tricyclo[8.2.1.0^3,8]trideca-3,5,7-triene 
• 1199-46-8 2-amino-4-tert-butylphenol 
• 98-29-3 4-tert-Butylcatechol 
• 98-54-4 para-tert-butylphenol 
• 1020-31-1 3,5-Di-tert-butylcatechol 
• 75-91-2 tert.-butylhydroperoxide 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 110306-99-5 6-tert-butyl-1,4-benzodioxin 

Downstream Products

• 36122-03-9 4-tert-butyl-5-methoxy-1,2-benzoquinone 
• 98-29-3 4-tert-Butylcatechol 
• 51950-61-9 dioxime dimethyl ether 
• 145030-77-9 (E)-4-tert-butyl-2-(methoxyimino)-3,5-cyclohexadien-1-one 
• 145030-78-0 (E)-5-tert-butyl-2-(methoxyimino)-3,5-cyclohexadien-1-one 
• 1020-31-1 3,5-Di-tert-butylcatechol 
• 84297-00-7 3,5-Di-t.-butylpyrocatecholacetat 
• 84296-64-0 1-(5-tert-Butyl-2,3-dihydroxy-phenyl)-ethanone 
• 80869-94-9 1,2-diacetoxy-4-tert-butyl-benzene 

Relevant articles and documents

IBS-catalyzed regioselective oxidation of phenols to 1,2-quinones with oxone

We have developed the first example of hypervalent iodine(V)-catalyzed regioselective oxidation of phenols to o-quinones. Various phenols could be oxidized to the corresponding o-quinones in good to excellent yields using catalytic amounts of sodium salts of 2-iodobenzenesulfonic acids (pre-IBSes) and stoichiometric amounts of Oxone as a co-oxidant under mild conditions. The reaction rate of IBS-catalyzed oxidation under nonaqueous conditions was further accelerated in the presence of an inorganic base such as potassium carbonate (K2CO3), a phase transfer catalyst such as tetrabutylammonium hydrogen sulfate (nBu4NHSO4), and a dehydrating agent such as anhydrous sodium sulfate (Na2SO4).

Bis-benzimidazolyl diamide copper (II) complexes: Synthesis, crystal structure and oxidation of substituted amino phenols

A new tetradentate ligand N,N′-Bis (1-butyl-benzimidazol-2-yl-methyl) -hexane-1,6-dicarboxamide (b-GBSA) has been utilized to synthesize mononuclear copper (II) complexes with inner sphere anionic ligands like NO3 -, Br- and Cl-. Two of the complexes [Cu(L)NO3]NO3 (1) and [Cu(L)Br]Br (2) have been structurally characterized. The geometry of copper (II) in (1) is a distorted octahedral with NO3- anion acting as a bidentate ligand, while for (2) the geometry is found to be a near square pyramidal. The complexes carry out the oxidation of substituted amino phenols in the presence of molecular oxygen. The oxidation gets blocked at the dihydrophenoxazinone stage for 2-amino-5-methyl phenol, and to o-quinone for 2-amino-4-tertiary butyl phenol, quite like the enzyme phenoxazinone synthase.

Aerobic Oxidation of Dihydroxyarenes Substrates Catalyzed by Polymer-Supported RuII-Pheox/Silica-Gel: A Beneficial Route for Purification of Industrial Water

A broad class of dihydroxyarenes were easily oxidized by aerobic oxygen to quinone products in excellent yields under the catalytic effect of polymer-supported RuII-Pheox/silica-gel catalyst. By using this combined catalyst, hydroquinone and catechol derivatives with electron-donating groups were easily oxidized by molecular oxygen to quinone products in 90% to >99% yield, while in the case of electron-withdrawing group, only 70% was obtained. The biologically useful 1,4-Naphthoqinone products were obtained in 83% to 90%. The catalyst was easily obtained and reused many times without a significant decrease in reactivity. Interestingly, a sample of industrial water contaminated with phenolic compounds was subjected to aerobic oxidation by using this catalyst, and the resultant quinones were detected within one day and the catalyst was removed and reused several times with different contami-nating samples with the same efficiency. Other catalytic oxidations by using this promising catalyst were investigated.

Controlling the catalytic aerobic oxidation of phenols

The oxidation of phenols is the subject of extensive investigation, but there are few catalytic aerobic examples that are chemo- and regioselective. Here we describe conditions for the ortho-oxygenation or oxidative coupling of phenols under copper (Cu)-catalyzed aerobic conditions that give rise to ortho-quinones, biphenols or benzoxepines. We demonstrate that each product class can be accessed selectively by the appropriate choice of Cu(I) salt, amine ligand, desiccant and reaction temperature. In addition, we evaluate the effects of substituents on the phenol and demonstrate their influence on selectivity between ortho-oxygenation and oxidative coupling pathways. These results create an important precedent of catalyst control in the catalytic aerobic oxidation of phenols and set the stage for future development of catalytic systems and mechanistic investigations.