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Tetramethyl-p-benzoquinone
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Name

Tetramethyl-p-benzoquinone

 EINECS 208-409-8
CAS No. 527-17-3 Density 1.039 g/cm3
PSA 34.14000 LogP 1.81100
Solubility N/A Melting Point 110-112 ºC(lit.)
Formula C10H12 O2 Boiling Point 230.1 ºC at 760 mmHg
Molecular Weight 164.204 Flash Point 83.6 ºC
Transport Information N/A Appearance YELLOW POWDER
Safety Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors. Risk Codes 36/37/38
Molecular Structure Molecular Structure of 527-17-3 (DUROQUINONE) Hazard Symbols IrritantXi
Synonyms

p-Benzoquinone,2,3,5,6-tetramethyl- (8CI); p-Benzoquinone, tetramethyl- (6CI); p-Benzoquinone,tetramethyl-, semiquinone (7CI); 2,3,5,6-Tetramethyl-1,4-benzoquinone;2,3,5,6-Tetramethyl-2,5-cyclohexadiene-1,4-dione;2,3,5,6-Tetramethyl-p-benzoquinone; 2,3,5,6-Tetramethylbenzoquinone;Duroquinone; NSC 2068; TMQ; Tetramethyl-1,4-benzoquinone; Tetramethyl-p-benzoquinone;Tetramethyl-p-quinone; Tetramethylbenzoquinone; Tetramethylquinone

Article Data 115

Tetramethyl-p-benzoquinone Synthetic route

527-17-3, 70128-24-4

Duroquinone

34505-31-2

1,3-Dimethyl-2-nitro-benzene

A

81-20-9

2,6-dimethylnitrobenzene

B

527-17-3

2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical

Conditions
ConditionsYield
In water; isopropyl alcohol Rate constant; Thermodynamic data; Irradiation; electron transfer reaction ΔE exc.;
527-17-3, 70128-24-4

Duroquinone

C36H46N4(2-)*Mg(2+)

A

527-17-3

2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical

B

C36H46N4(1-)*Mg(2+)

Conditions
ConditionsYield
In ethanol; dichloromethane at -68.1℃; Rate constant; Irradiation; dependence of photoelectron transfer upon excitation wavelength; delay time;
527-17-3, 70128-24-4

Duroquinone

C96H134N10O2(2-)*Mg(2+)

A

527-17-3

2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical

B

C96H134N10O2(1-)*Mg(2+)

Conditions
ConditionsYield
In ethanol; dichloromethane at -68.1℃; Rate constant; Irradiation; dependence of photoelectron transfer upon excitation wavelength; delay time;
527-17-3, 70128-24-4

Duroquinone

2683-82-1

2,3,7,8,12,13,17,18-octaethyl-porphyrin

A

527-17-3

2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical

B

2,3,7,8,12,13,17,18-octaethylporphyrin radical cation

Conditions
ConditionsYield
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

A

64-17-5

ethanol

B

527-17-3

2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical

Conditions
ConditionsYield
In benzonitrile Equilibrium constant;
527-17-3, 70128-24-4

Duroquinone

527-17-3

2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical

Conditions
ConditionsYield
With triethylamine In acetonitrile at 24℃; Kinetics; Further Variations:; Solvents; Irradiation;
64-17-5

ethanol

527-17-3

2,3,5,6-Tetramethyl-1,4-benzoquinone anion radical

2,3,5,6-Tetramethyl-[1,4]benzoquinone; compound with ethanol

Conditions
ConditionsYield
In benzonitrile Equilibrium constant;

Tetramethyl-p-benzoquinone Chemical Properties

Molecule structure of Tetramethyl-p-benzoquinone (CAS NO.527-17-3) :

IUPAC Name: 2,3,5,6-tetramethylcyclohexa-2,5-diene-1,4-dione 
Molecular Weight: 164.20108 g/mol
Molecular Formula: C10H12O2 
Density: 1.039 g/cm3 
Boiling Point: 230.1 °C at 760 mmHg 
Flash Point: 83.6 °C
Index of Refraction: 1.493
Molar Refractivity: 45.95 cm3
Molar Volume: 157.9 cm3
Polarizability: 18.21×10-24 cm3
Surface Tension: 30.6 dyne/cm 
Enthalpy of Vaporization: 46.67 kJ/mol
Vapour Pressure: 0.0672 mmHg at 25 °C
XLogP3: 2.2
H-Bond Acceptor: 2
Tautomer Count: 8
Exact Mass: 164.08373
MonoIsotopic Mass: 164.08373
Topological Polar Surface Area: 34.1
Heavy Atom Count: 12
Complexity: 268
Canonical SMILES: CC1=C(C(=O)C(=C(C1=O)C)C)C
InChI: InChI=1S/C10H12O2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h1-4H3
InChIKey: WAMKWBHYPYBEJY-UHFFFAOYSA-N
EINECS: 208-409-8
Product Categories: Anthraquinones, Hydroquinones and Quinones; Benzoquinones

Tetramethyl-p-benzoquinone Uses

 Tetramethyl-p-benzoquinone (CAS NO.527-17-3) is used in the formation of a "nanobrain" (16 duroquinone molecules surrounding a 17th in the middle).

Tetramethyl-p-benzoquinone Toxicity Data With Reference

1.    

mic-esc 60 µLg/plate

     MUREAV    Mutation Research. 467 (2000),41.
2.    

dnd-rat-lvr 400 µmol/L

     CALEDQ    Cancer Letters (Shannon, Ireland). 63 (1992),47.

Tetramethyl-p-benzoquinone Safety Profile

Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: GU5410000

Tetramethyl-p-benzoquinone Specification

 Tetramethyl-p-benzoquinone (CAS NO.527-17-3) is also called Duroquinone ; 2,3,5,6-Tetramethyl-1,4-benzoquinone ; 2,3,5,6-Tetramethyl-p-benzoquinone ; 2,3,5,6-Tetramethylbenzoquinone ; AI3-61045 ; CCRIS 2989 ; NSC 2068 ; Tetramethyl-1,4-benzoquinone ; Tetramethyl-p-quinone ; Tetramethylquinone ; p-Benzoquinone, 2,3,5,6-tetramethyl- ; p-Benzoquinone, tetramethyl- ; p-Benzoquinone, tetramethyl-, semiquinone ; 2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetramethyl- . Tetramethyl-p-benzoquinone (CAS NO.527-17-3) is yellow powder.

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