2460-77-7

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Di-tert-butyl-1,4-benzoquinone is used as an antibacterial agent for its ability to inhibit bacterial growth. It is particularly valuable in the development of new antibiotics to combat drug-resistant bacteria due to its natural origin and unique chemical structure.
Used in Chemical Research:
DTBBQ serves as a subject of study in chemical research, specifically in understanding the pressure dependence of ion migration rates. This knowledge can be applied to various fields, including material science and the development of new technologies that rely on ion movement.
Used in Marine Biology:
As a compound isolated from marine Streptomyces sp. VITVSK1, 2,5-Di-tert-butyl-1,4-benzoquinone contributes to the study of marine microorganisms and their potential applications in medicine and biotechnology. It can be used to explore the biodiversity of marine ecosystems and the bioactive compounds they produce.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 4545, 1981 DOI: 10.1021/jo00335a045Synthetic Communications, 10, p. 615, 1980 DOI: 10.1080/00397918008063598Tetrahedron Letters, 35, p. 5083, 1994 DOI: 10.1016/S0040-4039(00)73327-2

Flammability and Explosibility

Flammable

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

Upstream product

• 88-58-4 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol 
• 507-20-0 tertiary butyl chloride 
• 123-31-9 hydroquinone 
• 96-76-4 2,4-di-tert-Butylphenol 
• 18724-29-3 1,4-bis(trimethylsiloxy)-2,5-di-tert-butylbenzene 
• 73759-45-2 1,4-bis(tert-butyldimethylsiloxy)-2,5-di-(tert-butyl)benzene 
• 509-14-8 tetranitromethane 
• 7323-63-9 1,4-di-tert-butyl-2,5-dimethoxybenzene 
• 7705-08-0 iron(III) chloride 
• 22162-01-2 2,5-di-tert-butylbenzene-1,4-diamine 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 2406-04-4 4-(phenylimino)cyclohexa-2,5-dienone 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 900-02-7 1,4-diacetoxy-2,5-di-tert-butyl-benzene 
• 88-58-4 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol 
• 32299-99-3 2,5-di-tert-butyl-p-benzoquinone monoxime 
• 4857-75-4 1,2,4-triacetoxy-5-tert-butylbenzene 
• 136465-60-6 (3S,3aS,7aS)-5,7a-Di-tert-butyl-2,3-diphenyl-2,3,3a,7a-tetrahydro-benzo[d]isoxazole-4,7-dione 
• 18724-29-3 1,4-bis(trimethylsiloxy)-2,5-di-tert-butylbenzene 
• 134284-66-5 2,5-Di-t-butyl-4-hydroxy-4-perfluorooctyl-2,5-cyclohexadien-1-one 
• 90508-38-6 2,5-Di-tert-butyl-N,N'-dicyano-1,4-benzoquinonediimine 
• 105381-54-2 C₁₆H₂₀N₄ 
• 89049-59-2 5,7a-Di-tert-butyl-3-(2,3,5,6-tetramethyl-phenyl)-3a,7a-dihydro-benzo[d]isoxazole-4,7-dione 
• 77501-99-6 2,5-di-t-butyl-1-isobutylbenzene 
• 127558-27-4 2-t-butyl-5-isobutyl-1,4-dihydroxybenzene 
• 73685-60-6 2-(1,1-dimethylethyl)-5-(2-propenyl)-1,4-benzenediol 
• 74785-31-2 2-(2-butenyl)-5-tert-butylhydroquinone 

Relevant academic research and scientific papers

A rapid and efficient synthesis of quinone derivatives: Ru(II)-or Ir(I)-catalyzed hydrogen peroxide oxidation of phenols and methoxyarenes

Hydroquinone and methoxybenzene derivatives were catalytically oxidized promptly to the corresponding quinones in up to 99% yield. With a catalyst loading of 0.01 mol %, a maximum TON of 8.4 × 103 was attained in the case of Ru(II)-complex. Ru(II)(pybox-dh)(pydic) is able to enhance the hydrogen peroxide oxidation of substituted hydroquinones as well as methoxybenzenes, but Ir[(coe)2Cl]2 and Ir[(cod)Cl] 2 were found to be effective catalysts only for the former substrates under similar oxidation conditions.

Oxidation of hydroquinones with meso-hexakispentafluorophenyl [26]hexaphyrin(1.1.1.1.1.1)

Treatment of various hydroquinones and catechols with meso- pentafluorophenyl [26]hexaphyrin(1.1.1.1.1.1) provided the corresponding quinones quantitatively. The Royal Society of Chemistry 2006.

Zwitterion-induced organic-metal hybrid catalysis in aerobic oxidation

In many metal catalyses, the traditional strategy of removing chloride ions is to add silver salts via anion exchange to obtain highly active catalysts. Herein, we reported an alternative strategy of removing chloride anions from ruthenium trichloride using an organic [P+-N-] zwitterionic compound via multiple hydrogen bond interactions. The resultant organic-metal hybrid catalytic system has successfully been applied to the aerobic oxidation of alcohols, tetrahydroquinolines, and indolines under mild conditions. The performance of zwitterion is far superior to that of many other common Lewis bases or Br?nsted bases. Mechanistic studies revealed that the zwitterion triggers the dissociation of chloride from ruthenium trichloride via nonclassical hydrogen bond interaction. Preliminary studies show that the zwitterion is applicable to catalytic transfer semi-hydrogenation.

The impact of an isoreticular expansion strategy on the performance of iodine catalysts supported in multivariate zirconium and aluminum metal-organic frameworks

Iodine functionalized variants of DUT-5 (Al) and UiO-67 (Zr) were prepared as expanded-pore analogues of MIL-53 (Al) and UiO-67 (Zr). They were prepared using a combination of multivariate and isorecticular expansion strategies. Multivariate MOFs with a 25% iodine-containing linker was chosen to achieve an ideal balance between a high density of catalytic sites and sufficient space for efficient diffusion. Changes to the oxidation potential of the catalyst as a result of the pore-expansion strategy led to a decrease in activity with electron rich substrates. On the other hand, these larger frameworks proved to be more efficient catalysts for substrates with higher oxidation potentials. Recyclability tests for these larger MOFs showed sustained catalytic activity over multiple recycles.

A Facile and Selective Procedure for Oxidation of Hydroquinones using Silica Gel Supported Catalytic Cerium(IV) Ammonium Nitrate

A new procedure for oxidation of hydroquinones to quinones using a silica gel supported cerium(IV) ammonium nitrate-NaBrO3 reagent has been developed. This simple, easy to prepare and use, heterogeneous reagent is highly selective towards oxidation of 1,4-dihydroxybenzenes and produces high yields of quinones. Waste generated by using this procedure is minimal.

Homogeneous Pd-catalyzed transformation of terminal alkenes into primary allylic alcohols and derivatives

Synthesis of primary alcohols from terminal alkenes is an important process in both bulk and fine chemical syntheses. Herein, a homogeneous Pd-complex-catalyzed transformation of terminal alkenes into primary allylic alcohols, by using 5 mol % [Pd(PPh3)4] as a catalyst, and H2O, CO2, and quinone derivatives as reagents, is reported. When alcohols were used instead of H2O, allylic ethers were obtained. A proposed mechanism includes the addition of oxygen nucleophiles at the less-hindered terminal position of π-allyl Pd intermediates.

Preparation and catalytic performance of perfluorosulfonic acid-functionalized carbon nanotubes

Perfluorosulfonic acid-functionalized carbon nanotubes were prepared by liquid deposition of the perfluorosulfonic acid-polytetrafluoroethylene copolymer and characterized by N2 adsorption, scanning electron microscopy, transmission electron mi

Quinones synthesis via hydrogen peroxide oxidation of dihydroxy arenes catalyzed by homogeneous and macroporous-polymer-supported ruthenium catalysts

Ruthenium(II)/dimethyl phenyloxazoline (Ru(II)/dm-Pheox) complex 2a and its macroporous-polymeric-catalyst 4 were found to be very rapid and efficient catalysts in the hydrogen peroxide oxidation of 1,2- and 1,4-dihydroxy arenes. Most of the quinone products were delivered in 99% yield. The polymeric-catalyst 4 could be reused at least five times.

Enhanced activity over alkyl/aryl functionalized porous pillared-zirconium phosphates in liquid-phase reaction

A series of porous pillared-zirconium phosphates functionalized with methyl, ethyl, propyl and phenyl groups were prepared and characterized by SEM, 29Si MAS NMR, TG and N2 adsorption. Their total surface acidity and accessible one were measured by potentiometric titration of n-butylamine and liquid phase 2,6-di-tert-butyl-pyridine adsorption, respectively. The catalytic behaviors of these hybrid materials for alkylation of hydroquinone and esterification of lauric acid were compared. Not the total acid sites but the accessible ones play a crucial role in both reactions of alkylation and esterification. The accession for acid sites can be enhanced by the introduction of alkyl/aryl groups, due to the improved hydrophobicity of the surface.

μ-oxo-bridged hypervalent iodine(III) compound as an extreme oxidant for aqueous oxidations

We have found that in aqueous oxidations the -oxo-bridged hypervalent iodine trifluoroacetate reagent 1 {[(PhI(OCOCF]} is generally more reactive than the corresponding monomeric reagent, especially toward phenolic substrates. -Oxo-bridged 1 in aqueous media thus provided dearomatized quinones 3 in excellent yields in most cases compared to conventional phenyliodine(III) diacetate and bis(trifluoroacetate), as a result of the rapid oxidation of both phenols and naphthols 2. Furthermore, the oxidation reactions proceeded even in water using water-soluble -oxo oxidant 1, which has promise for -oxo-bridged reagent 1 to become the favored reagent over hydrophobic phenyliodine(III) diacetate and bis(trifluoroacetate). Georg Thieme Verlag Stuttgart New York.