14387-13-4

Basic information

• Product Name: 2,6-Di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadien-1-one
• Synonyms: 2,6-Di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadien-1-one;2,6-Di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadiene-1-one;2,6-Di-tert-butyl-4-methyl-4-(4-hydroxy-3,5-di-tert-butylphenyl)-2,5-cyclohexadien-1-one
• CAS NO: 14387-13-4
• Molecular Formula: C₂₉H₄₄O₂
• Molecular Weight: 424.66
• Mol File: 14387-13-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 153-154 °C
• Boiling Point: 465.9±45.0 °C(Predicted)
• Appearance: /
• Density: 0.982±0.06 g/cm3(Predicted)
• PKA: 11.83±0.50(Predicted)
• CAS DataBase Reference: 2,6-Di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadien-1-one(14387-13-4)
• EPA Substance Registry System: 2,6-Di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadien-1-one(14387-13-4)

Safety Data

• Hazardous Substances Data: 14387-13-4(Hazardous Substances Data)

Upstream product

• 4130-42-1 2,6-di-tert-butyl-4-ethylphenol 
• 2179-51-3 4-(2,6-di-tert-butyl-4-methylphenoxy)-2,6-di-tert-butyl-4-methyl-2,5-cyclohexadien-1-one 
• 128-39-2 2,6-di-tert-butylphenol 
• 131544-11-1 1-hydro-1'-methyl-3,5,3',5'-tetra-tert-butyl-2,5,2',5'-bis(cyclohexadiene)-4,4'-dione 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 6858-01-1 2,6-di-tert-butyl-4-methylphenoxy radical 

Relevant articles and documents

Construction of vicinal quaternary carbons via Cu-catalyzed dearomative radical addition

In this paper, we confirmed the dearomative addition of tertiary alkyl radicals onto BHT derivatives to form highly congested vicinal quaternary carbons to produce tert-alkylated styrenes in the presence of copper catalyst. Although there are three candid

The Reaction of the 2,6-Di-tert-butyl-4-methylphenoxy Radical with Phenols

Dimer 3 dissociates in solution to give the phenoxy radical 4.When solid 3 is dissolved in a solution of phenol 11a, radical 4 dehydrogenates the phenol to afford phenol 5 and phenoxy radical 12.Radical 12 couples with more 4 to afford principally bis(cyclohexadienone) 16a and a minor amount of the dimeric bis(cyclohexadienone) 13.The preferential formation of 16a over 13 is explained as the result of a solvent-cage reaction.Compounds 13 and 16a are isomerized in the presence of silica gel or triethylamine to 4,4'-dihydroxybiphenyl 14 and phenolic dienone 17a, respectively.Compound 13 is relatively stable in hexane at 30 deg C, while 16a slowly dissociates under these conditions to afford parent radicals 4 and 12.If 11a is present, radical 4 either recombines with 12 or dehydrogenates the phenol.Two radicals of 12 generated by the dissociation of 16a and the subsequent dehydrogenation of 11a couple to give 13.Therefore, dissolving 3 in hexane containing excess 11a and keeping the resulting solution at 30 deg C results in the preferential formation of 13.Dissolving 3 in triethylamine containing phenols 11 or 21 similarly affords dienones 17 or 23.The yields of these dienones increase with increasing electron-donating capability of the substituent of the phenol ring.

Unsymmetrical Anodic C-C Coupling of 2,6-Di-tert-butyl-4-methylphenol

Cyclic voltammetry of 2,6-di-tert-butyl-4-methylphenol (1) in acetonitrile in the presence of an aliphatic amine such as ethyl-, diethyl-, or triethylamine shows an ill-defined anodic wave - a socalled kinetic wave - around 0.5V vs. aqueous saturated calomel electrode, indicating an electron-transfer process preceded by a slow chemical reaction.Based on the estimated pKa value of 1 (pKa=12.55 in water at 25 deg C), the chemical reaction was ascribed to a slow hydrogen-bonding association of 1 and the added amine.Controlled potential electrolysis of 1 at the potential of the anodic wave gave an unsymmetrical dimer, 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadiene-1-one, as the main product.Side-chain aminated derivatives of 1, Ar-CH2NHEt, Ar-CH2NEt2, and Ar-CH2N+NEt3 (Ar=3,5-di-tert-butyl-4-hydroxyphenyl), are suggested to be the intermediates; that is, the process of dimer formation is explained in terms of cross-coupling of the phenoxyl radicals derived from 1 and the side-chain aminated phenols followed by expulsion of the aminomethyl group.Keywords - electrochemical oxidation; cyclic voltammetry; conrolled potential electrolysis; 2,6-di-tert-butyl-4-methylphenol; oxidative dimerization; phenol coupling