2460-77-7

Basic information

• Product Name: 2,5-Di-tert-butyl-1,4-benzoquinone
• Synonyms: 2,5-di-tert-butyl-p-benzoquinon;4-dione,2,5-bis(1,1-dimethylethyl)-5-cyclohexadiene-1;5-Cyclohexadiene-1,4-dione,2,5-bis(1,1-dimethylethyl)-2;2,5-DI-TERT-BUTYL-P-QUINONE;2,5-DI-TERT-BUTYL-P-BENZOQUINONE;2,5-DI-TERT-BUTYL-1,4-BENZOQUINONE;2,5-DI-TERT-BUTYLBENZOQUINONE;2,5-tert-butyl-1,4-benzoquinone
• CAS NO: 2460-77-7
• Molecular Formula: C₁₄H₂₀O₂
• Molecular Weight: 220.31
• EINECS: 219-552-0
• Product Categories: Anthraquinones, Hydroquinones and Quinones;Benzoquinones;C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 2460-77-7.mol
• Article Data: 42

Chemical Properties

• Melting Point: 152-154 °C(lit.)
• Boiling Point: 321.25°C (rough estimate)
• Flash Point: 106.247 °C
• Appearance: Yellow to golden crystalline powder
• Density: 1.0106 (rough estimate)
• Vapor Pressure: 0.00281mmHg at 25°C
• Refractive Index: 1.4970 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 18.716mg/L at 25℃
• BRN: 2047945
• CAS DataBase Reference: 2,5-Di-tert-butyl-1,4-benzoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Di-tert-butyl-1,4-benzoquinone(2460-77-7)
• EPA Substance Registry System: 2,5-Di-tert-butyl-1,4-benzoquinone(2460-77-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: GU5140000
• TSCA: Yes
• Hazardous Substances Data: 2460-77-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow to golden crystalline powder

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

General Description

2,5-Di-tert-butyl-1,4-benzoquinone (DTBBQ) is an 2,5-disubstituted quinone. It is an antibacterial compound. It has been isolated from marine Streptomyces sp. VITVSK1. Pressure dependance on the intramolecular and intermolecular migration rates of Na+ and K+ in a 2,5-di-tert-butyl-1,4-benzoquinone ion pair have been evaluated by using a high-pressure EPR technique.

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

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

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 
• 134284-66-5 2,5-Di-t-butyl-4-hydroxy-4-perfluorooctyl-2,5-cyclohexadien-1-one 
• 89049-61-6 5,7a-Di-tert-butyl-3-(4-chloro-phenyl)-3a,7a-dihydro-benzo[d]isoxazole-4,7-dione 
• 58459-46-4 2,5-Di-tert-butyl-1,4-dimethyl-cyclohexa-2,5-diene-1,4-diol 
• 267226-99-3 5,7a-di-tert-butyl-3-(4-fluoro-phenyl)-3a,7a-dihydro-benzo[d]isoxazole-4,7-dione 
• 10472-70-5 2,5-di-tert-butyl-p-dinitrobenzene 
• 160513-17-7 2,5-di-tert-butyl-p-dinitrosobenzene 
• 160513-14-4 2,5-di-tert-butyl-p-benzoquinone dioxime 
• 95413-34-6 4,7-Di-tert-butyl-3-(4-chloro-phenyl)-4-hydroxy-4H-benzo[d]isoxazol-5-one 
• 95413-35-7 3-(4-Bromo-phenyl)-4,7-di-tert-butyl-4-hydroxy-4H-benzo[d]isoxazol-5-one 
• 145383-58-0 4,7-Di-tert-butyl-4-hydroxy-3-(2,4,6-trimethyl-phenyl)-4H-benzo[d]isoxazol-5-one 
• 145383-59-1 4,7-Di-tert-butyl-4-hydroxy-3-(2,3,5,6-tetramethyl-phenyl)-4H-benzo[d]isoxazol-5-one 

Relevant articles and documents

Practical Large-Scale Oxidation of 1,4-Hydroquinones to 1,4-Benzoquinones Using Hydrogen Peroxide/Catalytic Diphenyl Diselenide

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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.

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.