527-17-3

Basic information

• Product Name: DUROQUINONE
• Synonyms: 2,3,5,6-Tetramethylbenzo-1,4-quinone;2,3,5,6-Tetramethylbenzoquinone;2,3,5,6-tetramethyl-p-benzoquinon;2,3,5,6-Tetramethyl-p-benzoquinone;2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetramethyl-;4-dione,2,3,5,6-tetramethyl-5-cyclohexadiene-1;p-Benzoquinone, tetramethyl-;tetramethyl-p-benzoquinon
• CAS NO: 527-17-3
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• EINECS: 208-409-8
• Product Categories: Anthraquinones, Hydroquinones and Quinones;Benzoquinones
• Mol File: 527-17-3.mol
• Article Data: 55

Chemical Properties

• Melting Point: 110-112 °C(lit.)
• Boiling Point: 251.67°C (rough estimate)
• Flash Point: 83.6 ºC
• Appearance: /
• Density: 1.0326 (rough estimate)
• Vapor Pressure: 0.0672mmHg at 25°C
• Refractive Index: 1.5220 (estimate)
• Storage Temp.: under inert gas (Argon)
• Merck: 14,3470
• BRN: 1909128
• CAS DataBase Reference: DUROQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: DUROQUINONE(527-17-3)
• EPA Substance Registry System: DUROQUINONE(527-17-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: GU5410000
• Hazardous Substances Data: 527-17-3(Hazardous Substances Data)

Usage

Chemical Properties

YELLOW POWDER

Uses

Tetramethyl-1,4-benzoquinone is an antioxidant.

Synthesis Reference(s)

The Journal of Organic Chemistry, 34, p. 1216, 1969 DOI: 10.1021/jo01257a007

Purification Methods

Crystallise duraquinone from 95% EtOH. Dry it in vacuo.[Beilstein 7 H 669, 7 III 3417, 7 IV 2101.]

InChI:InChI=1/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3

Synthetic route

Duroquinone (527-17-3, 70128-24-4) + 1,3-Dimethyl-2-nitro-benzene (34505-31-2) → 2,6-dimethylnitrobenzene (81-20-9) + 2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical (527-17-3)

Conditions	Yield
In water; isopropyl alcohol Rate constant; Thermodynamic data; Irradiation; electron transfer reaction ΔE exc.;

Duroquinone (527-17-3, 70128-24-4) + C36H46N4(2-)*Mg(2+) → 2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical (527-17-3) + C36H46N4(1-)*Mg(2+)

Conditions	Yield
In ethanol; dichloromethane at -68.1℃; Rate constant; Irradiation; dependence of photoelectron transfer upon excitation wavelength; delay time;

Duroquinone (527-17-3, 70128-24-4) + C96H134N10O2(2-)*Mg(2+) → 2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical (527-17-3) + C96H134N10O2(1-)*Mg(2+)

Conditions	Yield
In ethanol; dichloromethane at -68.1℃; Rate constant; Irradiation; dependence of photoelectron transfer upon excitation wavelength; delay time;

Duroquinone (527-17-3, 70128-24-4) + 2,3,7,8,12,13,17,18-octaethyl-porphyrin (2683-82-1) → 2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical (527-17-3) + 2,3,7,8,12,13,17,18-octaethylporphyrin radical cation

Conditions	Yield
In ethanol; dichloromethane at -68.1℃; Rate constant; Irradiation; dependence of photoelectron transfer upon excitation wavelength; delay time;

2,3,5,6-Tetramethyl-[1,4]benzoquinone; compound with ethanol → ethanol (64-17-5) + 2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical (527-17-3)

Conditions	Yield
In benzonitrile Equilibrium constant;

Duroquinone (527-17-3, 70128-24-4) → 2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical (527-17-3)

Conditions	Yield
With triethylamine In acetonitrile at 24℃; Kinetics; Further Variations:; Solvents; Irradiation;

ethanol (64-17-5) + 2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical (527-17-3) → 2,3,5,6-Tetramethyl-[1,4]benzoquinone; compound with ethanol

Conditions	Yield
In benzonitrile Equilibrium constant;

Upstream product

• 110-22-5 diacetyl peroxide 
• 935-92-2 2,3,5-Trimethyl-1,4-benzoquinone 
• 95-93-2 1,2,4,5-tetramethylbenzene 
• 2819-86-5 pentamethylphenol 
• 95-63-6 1,2,4-Trimethylbenzene 
• 64-19-7 acetic acid 
• 2416-94-6 2,3,6-trimethylphenol 
• 527-18-4 Durohydroquinone 
• 7697-37-2 nitric acid 
• 7705-08-0 iron(III) chloride 
• 600-14-6 2,3-Pentanedione 
• 7732-18-5 water 
• 7758-99-8 copper(II) sulfate 
• 57856-10-7 3,3-Dichlor-2-pentanon 

Downstream Products

• 527-18-4 Durohydroquinone 
• 35079-56-2 [2,2']Bi[[1,3]dithiolylidene] 
• 779976-14-6 durosemiquinone anion radical 
• 82363-84-6 1,2,4,5-Tetramethyl-3,6-bis-trimethylsilanyloxy-benzene 
• 91238-42-5 1-Benzyl-1,4-dihydro-pyridine-3-carboxylic acid amide; compound with 2,3,5,6-tetramethyl-[1,4]benzoquinone 
• 96914-21-5 tetramethyl-1,4-benzoquinone-tetramethyl-1,4-hydroquinone 
• 82414-91-3 4-(triethylsilyloxy)-2,3,5,6-tetramethylphenoxy 
• 130021-86-2 C₁₉H₃₉O₂Si₄ 
• 90508-37-5 N,N'-Dicyano-2,3,5,6-tetramethyl-1,4-benzoquinonediimine 
• 16404-66-3 4-hydroxy-2,4,6-trimethyl-cyclohexa-2,5-dienone 
• 52103-92-1 4-Hydroxy-3,4,5,5-tetramethyl-2-cyclohexen-1-on 
• 55776-84-6 4-hydroxy-3,4,5-trimethyl-2,5-cyclohexadien-1-one 
• 31464-76-3 4-hydroxy-2,3,4,5,6-pentamethyl-2,5-cyclohexadien-1-one 
• 61548-94-5 4-ethoxytetramethylphenol 

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