719-22-2

Usage

Uses

Used in Polymer and Plastics Industry:
2,6-Di-tert-butylbenzoquinone is used as a polymerization inhibitor and antioxidant for the production of various polymers and plastics. It helps prevent the premature polymerization of monomers and protects polymers from oxidative degradation, thereby enhancing the stability and longevity of the final products.
Used in Personal Care and Cosmetic Products:
Leveraging its anti-microbial and anti-fungal properties, 2,6-Di-tert-butylbenzoquinone is utilized in the formulation of certain personal care and cosmetic products. It contributes to the preservation and shelf life of these products by inhibiting the growth of microorganisms that can cause spoilage and degradation.

InChI:InChI=1/C14H20O2/c1-13(2,3)10-7-9(15)8-11(12(10)16)14(4,5)6/h7-8H,1-6H3

Upstream product

• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 732-26-3 2,4,6-tri-tert-butylphenoxol 
• 489-01-0 2,6-Di-t-butyl-4-methoxyphenol 
• 1620-98-0 3,5-di-t-butyl-4-hydroxybenzaldehyde 
• 110-86-1 pyridine 
• 1988-75-6 4-bromo-2,4,6-tri-tert-butyl-2,5-cyclohexadiene-1-one 
• 107-21-1 ethylene glycol 
• 288-32-4 1H-imidazole 
• 67-56-1 methanol 
• 1620-64-0 ethyl 4-hydroxy-3,5-di-tert-butylbenzoate 
• 75697-72-2 4-bromo-4-(1-hydroxypropyl)-2,6-di-t-butylcyclohexa-2,5-dienone 
• 75-91-2 tert.-butylhydroperoxide 
• 56-23-5 tetrachloromethane 
• 955-02-2 2,6-di-tert-butyl-4-diazo-2,5-cyclohexadien-1-one 

Downstream Products

• 2444-28-2 2,6-di-tert-butyl-4-hydroxyphenol 
• 15052-28-5 2,6-di-tert-butyl-1,4-benzoquinone monooxime 
• 3791-04-6 (+/-)-5r,6t-di-tert-butyl-2-hydroxy-cyclohex-2-ene-1,4-dione 
• 20031-57-6 2,6-Di-tert-butyl-4-phenylazo-phenol 
• 31568-57-7 C₂₁H₂₈N₂O 
• 33718-73-9 4-(4-Amino-3,5-di-tert-butyl-phenylimino)-2,6-di-tert-butyl-cyclohexa-2,5-dienone 
• 14329-32-9 2,6-di-tert-butyl-[1,4]benzoquinone-4-(4-dimethylamino-phenylimine) 
• 33974-38-8 4-morpholino-2,6-di-tert-butylphenol 
• 136366-98-8 4-piperazino-2,6-di-tert-butylphenol 
• 67175-53-5 2,6-Di-tert-butylbenzoquinone-4-oxime methyl ether 
• 102520-20-7 2,6-Di-tert-butyl-4-hex-1-ynyl-4-hydroxy-cyclohexa-2,5-dienone 
• 55872-73-6 2,6-Di-tert-butyl-4-(pyrrol-1-ylimino)-cyclohexa-2,5-dienone 
• 84812-24-8 2,6-Di-tert-butyl-4-hydroxy-4-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)-cyclohexa-2,5-dienone 
• 14694-44-1 4-(Diaethylphosphonooxy)-2,6-di-tert.-butylphenoxyl 

Relevant academic research and scientific papers

A 1:1 copper-dioxygen adduct is an end-on bound superoxo copper(II) complex which undergoes oxygenation reactions with phenols

Employing a strongly electron-donating tripodal tetradentate ligand along with a reaction strategy designed to suppress binuclear peroxo complex formation, an end-on bound superoxo-copper(II) complex [CuII(NMe2-TMPA)(O2-)]+ (1) has been generated in solution [UV-vis (THF, -85 °C): λmax = 418 nm (ε, 4300 M-1 cm-1), 615 nm (ε, 1100), 767 nm (ε, 840)]. Resonance Raman spectroscopy employing isotopically substituted dioxygen (including mixed isotope 16/18O2) proves the end-on superoxo CuII(O2-) structural formulation, ν(O-O) = 1121 cm-1; ν(Cu-O) = 472 cm-1. The first demonstration of CuII(O2-) oxidative reactivity with exogenous substrates, likely involving H-atom abstraction chemistry, comes with the finding that 1 effects the oxygenation and hydroperoxylation of substituted phenols. Copyright

An efficient preparation of 2,6-di-t-butyl-1,4-benzoquinone

A convenient and high yielding preparation of 2,6-di-t-butyl-1,4-benzoquinone from the iron-catalyzed oxidation of 2,4,6-tri-t-butylphenol with t-butyl hydroperoxide (TBHP) under acidic conditions is reported.

The synthesis, characterization, DNA/protein interaction, molecular docking and catecholase activity of two Co(II) complexes constructed from the aroylhydrazone ligand

Two Co(II) complexes, Co(BBH)phenMeCN (1) and Co(BSH)phenMeCN (2) (HBBH = benzophenone benzoyl hydrazone, HBSH = benzophenone salicylylhydrazone ligand and phen = 1,10-phenanthroline) were prepared and characterized by single X-ray crystallography. The investigation of the complexes binding with herring sperm DNA (HS-DNA) revealed that stronger binding interaction exists between the complexes and HS-DNA compared to the corresponding free ligands. And both complexes can bind to DNA through intercalation of the phenyl rings between adjacent base pairs in the double helix. Meanwhile, bovine serum albumin (BSA) binding studies reveal the complexes can effectively interact with BSA and change the secondary structure of BSA. Superoxide dismutase (SOD) mimic activity of the complexes was investigated and the results showed that complex 2 showed a stronger radical scavenging potency against O2 .- radical with an IC50 value of 16.10 μM. The catecholase-like activity of both complexes has been investigated with 3,5-di-tert-butylcatechol (3,5-DTBC) as the substrate in methanol solution under completely aerobic conditions. The catalytic reaction follows Michaelis-Menten enzymatic reaction kinetics with turnover numbers (kcat) of 34.14 h?1 and 30.36 h?1 for complex 1 and complex 2, respectively.

Effect of structural variation on enzymatic activity in tetranuclear (Cu4) clusters with defective cubane core

The stimulus to the modeling of enzyme functioning sites comes from their potential to give insight into the natural enzyme’s mechanistic pathways, ascertain the role of that different metal ion in the active site and construct better catalysts motivated by nature. The presence of metal ion leads to the activation of molecular oxygen in the metalloenzymes. The metalloenzymes such as the catechol oxidase (CO) enzyme that oxidizes the catechol to corresponding quinones which eventually protect damage tissues from plant and pathogen. Thus, the design and characterization of catalysts used as selectively and efficiently oxidation reactions have grown to be unique challenges for modern inorganic chemists. In this work, two novel tetranuclear complexes (1 and 2) have been synthesized in excellent yield. The complexes were characterized using various spectroscopic techniques such as FTIR, UV–Visible and PXRD pattern. The structure of 1 and 2 was elucidated by SC-XRD (single crystal X-ray diffraction) analysis. The magnetic study reveals the presence of the antiferromagnetic nature of 1 and 2. Both 1 and 2 shows a very good catecholase-like activity by oxidizing the catechol to analogous quinone in methanolic solution. Thus, a structure-activity relationship can further help us design other substituted tetranuclear complexes with enhanced catecholase like activity. Communicated by Ramaswamy H. Sarma.

Insight into the crystallization process: Relationships between crystal structures and properties of copper(ii) coordination polymers containing dimethylbis(4-pyridyl)silane

A systematic investigation into the favorable reaction conditions for construction of copper(ii) coordination polymers was carried out. Various reactions of copper(ii) bromide with dimethylbis(4-pyridyl)silane (L) produce two kinds of skeletal structures: the 1D loop-chain and the square-tubular helix. The fast-formation condition affords the 1D loop-chain, whereas the slow-formation condition yields the helical structure. The formation of significant condition-dependent structures can be partially attributed to the nature of the bromide anion and angle strain around the copper(ii) cation. The relationships between structures and physicochemical properties such as anion exchangeability, catalytic oxidation of 3,5-di-tert-butylcatechol, and thermal properties are discussed in these pages.

Mononuclear Cu(II) complex of an oxime ligand derived from N-Heterocyclic hydrazide: Synthesis, spectroscopy, electrochemistry, DFT calculations and catecholase activity

A new oxime derivative N-heterocyclic hydrazide ligand, N'-[(1E,2E)-2-(hydroxyimino)-1-methylpropylidene]-2-[(4-methyl-5-phenyl-4H-1,2,4-triazol-3-l)thio] acetohydrazide (1) and its mononuclear copper(II) complex (1a) have been synthesized and characterized by using IR, UV–Vis, NMR and MALDI-TOF mass spectrometry. DFT-based molecular orbital energy calculations and electrochemical behaviors of the compounds have been also studied to explain redox potential of the compounds. The catecholase-mimetic activity of the Cu(II) complex (1a) has been investigated by monitoring the formation of 3,5-di-tert-butyl-benzoquinone from 3,5-di-tert-butylcatechol. Irreversible electrochemical ring-closing of the ligand by oxidation is proposed. Electrochemical ring-closing reaction is shielded by the coordination of Cu(II) to the oxime moiety of the ligand and the title complex undergoes quasi-reversible oxidation and irreversible reduction. Under aerobic conditions, the title copper(II) complex behaves as an effective catalyst towards oxidation of 3,5-di-tert-butylcatechol to its corresponding quinone derivative in MeOH. The turnover number was found as 100.1 h?1.

A N3S(thioether)-ligated CuII-superoxo with enhanced reactivity

Previous efforts to synthesize a cupric superoxide complex possessing a thioether donor have resulted in the formation of an end-on trans-peroxo-dicopper(II) species, [{(Ligand)CuII}2(μ-1,2-O22-)]2+. Redesign/modification of previous N3S tetradentate ligands has now allowed for the stabilization of the monomeric, superoxide product possessing a S(thioether) ligation, [(DMAN3S)CuII(O2?-)]+ (2S), as characterized by UV-vis and resonance Raman spectroscopies. This complex mimics the putative CuII(O2?-) active species of the copper monooxygenase PHM and exhibits enhanced reactivity toward both O-H and C-H substrates in comparison to close analogues [(L)CuII(O2?-)]+, where L contains only nitrogen donor atoms. Also, comparisons of [(L)CuII/I]n+ compound reduction potentials (L = various N4 vs DMAN3S ligands) provide evidence that DMAN3S is a weaker donor to copper ion than is found for any N4 ligand-complex.

Liquid Phase Oxidation of 2,6-Di-t-butylphenol by Molecular Oxygen Using Magnesium Oxide Catalysts Modified with Metal Ion

Mn(II), Co(II), Cu(II), or Fe(III) ion containing magnesium oxides catalyzed oxidation of 2,6-di-t-butylphenol to quinones by molecular oxygen. 98percent Yield to 1,1'-bis(4-oxo-3,5-di-t-butylcyclohexadienylidene) was obtained with 16.7 wtpercent Mn ion containing magnesium oxide catalyst.

Evaluation of catacholase mimicking activity and apoptosis in human colorectal carcinoma cell line by activating mitochondrial pathway of copper(II) complex coupled with 2-(quinolin-8-yloxy)(methyl)benzonitrile and 8-hydroxyquinoline

To evaluate the cytotoxic potential of metal-based chemotherapeutic candidate towards the colorectal cancer, we have synthesized a new copper(II) complex [Cu(qmbn)(q)(Cl)] (1) (where, qmbn = 2-(quinolin-8-yloxy)(methyl)benzonitrile and q = 8-hydroxyquinoline) and structurally characterized by single crystal X-ray, Powder-XRD, FTIR and thermogravimetric analysis (TGA). The structural analysis reveals that copper(II) ions exist in a distorted square pyramidal (τ = ~0.1), with ligation of a chloride ion, oxygen atom and two nitrogen atoms at equatorial position and one oxygen atom at apical position. The cytotoxicity potential of complex 1 was executed against human colorectal cell lines (HCT116), which showed that 1 induces mitochondrion-mediated apoptotic cell death via activation of the Bax (pro-apoptotic protein) caspases-3 and 9 proteins. Interestingly, complex 1 was found to be a good candidate as electron-transfer catalyst which mimics catacholase with high turnover frequency (kcat = 1.03 × 102 h?1) for the conversion of the model substrate 3,5-di-tertbutylcatechol (3,5-DTBC) to 3,5-di-tertbutylquinone (3,5-DTBQ). Furthermore, molecular docking studies revealed that complex 1 was successfully localized inside the binding pocket of protein kinase (Akt), which validate the mechanism and mode of interaction of 1 that displayed cytotoxic activity experimentally. The obtained outcomes reveal that the complex 1 could be utilized as an encouraging perspective in the development of new therapeutic candidate for colon cancer.

Dioxygen Adducts of Cobalt(II) Complexes of 6,6'-Bis(p-substituted benzoylamino)-2,2'-bipyridines and Their Cytalytic Activities in Oxygenation of 2,6-Di-tert-butylphenol

The oxygen affinities and properties of oxygen adducts of complexes has been studied by cyclic voltammetry and IR, electronic and ESR spectroscopy.The complexes exhibited oxygen-binding ability in the presence of an appropriate axial base ligand (B), and the oxygen adducts were of the end-on bonded CoIII(O2(1-)) type (CoL(B)(O2)>.More complete electron transfer from the metal centre to the oxygen was indicated compared to that with .Electron-donating substituents gave higher concentrations of the oxygen adducts.The superior catalytic activity of these complexes, especially the Me- and But-substitued derivatives, in the oxygenation of 2,6-di-tert-butylphenol to the corresponding quinone is interpreted in terms of the reactivity of the co-ordinated oxygen and the oxygen affinity of the complexes.