O-Benzoquinone supplier | CasNO.583-63-1

Name
2-benzoquinone
EINECS
CAS No. 583-63-1
Article Data89
CAS DataBase
Density 1.256g/cm³
Solubility
Melting Point 65°C (rough estimate)
Formula C6H4 O2
Boiling Point 213.3°Cat760mmHg
Molecular Weight 108.097
Flash Point 76.4°C
Transport Information
Appearance
Safety A poison. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms o-Benzoquinone(8CI); 1,2-Benzoquinone; o-Quinone
PSA 34.14000
LogP 0.25060

Synthetic route

: 120-80-9
benzene-1,2-diol

: 583-63-1
ortoquinone

Conditions

Conditions	Yield
With 2,2'-bipyridylchromium peroxide In benzene for 0.5h; Product distribution; Heating; effect of various chromium(VI) based oxidants;	100%
With barium ferrate(VI) In benzene for 0.7h; Product distribution; Heating;	100%
With 2,2'-bipyridylchromium peroxide In benzene for 0.5h; Heating;	100%

: 95-54-5
1,2-diamino-benzene

: 583-63-1
ortoquinone

Conditions

Conditions	Yield
With sodium hypochlorite; Dowex 1X8-200 - chloride form In dichloromethane for 2.5h; Oxidation;	95%
With Montmorillonite K10; iodic acid at 65℃; microwave irradiation;	68%

: 90-05-1
2-methoxy-phenol

: 583-63-1
ortoquinone

Conditions

Conditions	Yield
With potassium hydroxide; lithium perchlorate In water; acetonitrile at 0℃; anodic oxidation at Pt electrode;	93%
With sodium periodate
Multi-step reaction with 5 steps 1: potassium carbonate / acetonitrile / 0 °C 2: lithium diisopropyl amide / tetrahydrofuran / -78 - 20 °C 3: water; sodium tetrahydroborate / tetrahydrofuran 4: 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; nitric acid; hydrogenchloride; oxygen / acetonitrile; water / 20 h / 45 °C / 760.05 Torr 5: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; methanol / 4 h / 70 °C / pH 10 View Scheme

: 95-55-6
2-amino-phenol

: 583-63-1
ortoquinone

Conditions

Conditions	Yield
With sodium hypochlorite; Dowex 1X8-200 - chloride form In ethyl acetate for 2.5h; Oxidation;	91%
With Montmorillonite K10; iodic acid at 67℃; for 0.00555556h; microwave irradiation;	76%
With cetyltrimethylammonium cerium(IV) nitrate In 1,4-dioxane for 1h; Heating;	60%
With sodium bromate; sulfuric acid In water at 25℃; Kinetics; Mechanism; Reagent/catalyst; Concentration; Temperature;

: 13031-53-3
3-hydroxy-2-phenyl-1H-inden-1-one

: 120-80-9
benzene-1,2-diol

A: 2-(3,4-dihydroxyphenyl)-2-phenyl-2H-indene-1,3-dione

B: 583-63-1
ortoquinone

Conditions

Conditions	Yield
With sodium acetate In water; acetonitrile Electrochemical reaction;	A 90% B n/a

...Expand

: 33802-06-1
di-tert-butyliminoxyl

: 120-80-9
benzene-1,2-diol

: 583-63-1
ortoquinone

Conditions

Conditions	Yield
at -30℃;	80%

: 108-95-2
phenol

: 583-63-1
ortoquinone

Conditions

Conditions	Yield
With <(2,2'-bipyridine)(2,2':6',2''-terpyridine)RuO>2+; phosphate buffer pH 6.8 for 4h; Ambient temperature; electrocatalytic oxidation with Ru(IV)-complex;	71%
With potassium bromate; V(IV) In sulfuric acid; acetic acid at 30℃; Rate constant;
With potassium iodate; sulfuric acid In methanol; water at 30℃; Rate constant; Thermodynamic data; ΔH(exit.), ΔS(excit.), ΔG(excit.), various concentrations of H2SO4,methanol : water mixtures;

: 10548-77-3
1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one

A: 583-63-1
ortoquinone

B: 90-05-1
2-methoxy-phenol

C: 93-07-2
Veratric acid

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; methanol at 70℃; for 4h; pH=10;	A 22% B 17% C 71%

...Expand

: 255-37-8
benzo[1,4]dioxine

A: 583-63-1
ortoquinone

B: 120-80-9
benzene-1,2-diol

Conditions

Conditions	Yield
With ozone 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, -78 deg C, irradiation; Yield given. Multistep reaction;	A n/a B 51%
With ozone 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, -78 deg C, irradiation; Yield given. Multistep reaction;	A 29% B n/a

: 110851-16-6
2,9,11,12,13-Pentaoxa-tricyclo[8.2.1.03,8]trideca-3,5,7-triene

A: 583-63-1
ortoquinone

B: 120-80-9
benzene-1,2-diol

Conditions

Conditions	Yield
In dichloromethane at -78℃; for 1h; Irradiation;	A 29% B 51%

: 90-01-7
salicylic alcohol

A: 583-63-1
ortoquinone

B: 3-hydroxymethyl-o-benzoquinone

C: 90-02-8
salicylaldehyde

Conditions

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; tetramethylcucurbit[6]uril In dimethylsulfoxide-d6; chloroform-d1 at 30℃; for 1h; Kinetics; Sealed tube;	A 36% B 19% C 21%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethylsulfoxide-d6; chloroform-d1 at 30℃; for 1h; Sealed tube;	A 25% B 26% C 31%

...Expand

: 19021-48-8
1,2-benzosemiquinone anion radical

A: 583-63-1
ortoquinone

B: 120-80-9
benzene-1,2-diol

Conditions

Conditions	Yield
With sodium azide; phosphate buffer; dinitrogen monoxide In water Mechanism; Rate constant; Irradiation;

: 71-43-2
benzene

: 583-63-1
ortoquinone

Conditions

Conditions	Yield
With ozone In dichloromethane at 25℃; Rate constant; Mechanism; correlations of relative rate data with various molecular orbital parameters;

: 108-95-2
phenol

A: 583-63-1
ortoquinone

B: 106-51-4
p-benzoquinone

Conditions

Conditions	Yield
With {Ru(IV)(2,2'-bipyridine)2(pyridine)O}(2+) In [D3]acetonitrile at 25℃; Kinetics; Thermodynamic data; Mechanism; further oxidant, solvents and temperatures; kinetic deuterium isotope effect; ΔH(excit.), ΔS(excit.);	A 12 % Spectr. B 88 % Spectr.

: 71-43-2
benzene

A: 583-63-1
ortoquinone

B: 120-80-9
benzene-1,2-diol

C: 123-31-9
hydroquinone

D: 106-51-4
p-benzoquinone

E: 108-95-2
phenol

Conditions

Conditions	Yield
With pyridine; oxygen; iron(III) octaethyl porphirin In ethanol at 24.9℃; under 760 Torr; Product distribution; Mechanism; Irradiation; var. of catalyst, base, pH;

...Expand

: 108-95-2
phenol

A: 583-63-1
ortoquinone

B: 120-80-9
benzene-1,2-diol

C: 123-31-9
hydroquinone

D: 106-51-4
p-benzoquinone

Conditions

Conditions	Yield
With pyridine; buffer pH 11; oxygen; iron(III) octaethyl porphirin In ethanol at 24.9℃; under 760 Torr; Product distribution; Mechanism; Irradiation; var. of catalyst, base, pH;

...Expand

: 28383-65-5
ethyl 2-diazo-3-oxo-3-phenylpropanoate

: 120-80-9
benzene-1,2-diol

A: 583-63-1
ortoquinone

B: 94-02-0
ethyl 3-oxo-3-phenylpropionate

Conditions

Conditions	Yield
copper In benzene Oxidation;

...Expand

: 7732-18-5
water

: 120-80-9
benzene-1,2-diol

Ce(SO4)2: Ce(SO4)2

: 583-63-1
ortoquinone

...Expand

: 60-29-7
diethyl ether

: 120-80-9
benzene-1,2-diol

silver oxide: silver oxide

: 583-63-1
ortoquinone

...Expand

: 120-80-9
benzene-1,2-diol

A: 583-63-1
ortoquinone

B 24-: 24-

Conditions

Conditions	Yield
With hexacyanoruthenate(III); sodium perchlorate In perchloric acid; water at 25℃; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.);

: 118-92-3
anthranilic acid

A: 583-63-1
ortoquinone

B N2, CO2: N2, CO2

Conditions

Conditions	Yield
With ammonium metavanadate; sulfuric acid In hydrogenchloride; water for 0.416667h; Product distribution; micro determination;

: 99-05-8
meta-aminobenzoic acid

A: 583-63-1
ortoquinone

B: 106-51-4
p-benzoquinone

C N2, CO2: N2, CO2

Conditions

Conditions	Yield
With ammonium metavanadate; sulfuric acid In hydrogenchloride; water for 0.333333h; Product distribution; micro determination;

...Expand

: 95-54-5
1,2-diamino-benzene

A: 583-63-1
ortoquinone

B N2: N2

Conditions

Conditions	Yield
With ammonium metavanadate; sulfuric acid In hydrogenchloride; water for 0.25h; Product distribution; micro determination;

: 95-55-6
2-amino-phenol

A: 583-63-1
ortoquinone

B N2: N2

Conditions

Conditions	Yield
With ammonium metavanadate; sulfuric acid In hydrogenchloride; water for 0.166667h; Product distribution; micro determination;

: 108-45-2
m-phenylenediamine

A: 583-63-1
ortoquinone

B: 106-51-4
p-benzoquinone

C N2: N2

Conditions

Conditions	Yield
With ammonium metavanadate; sulfuric acid In hydrogenchloride; water for 0.25h; Product distribution; micro determination;

...Expand

: 591-27-5
m-Hydroxyaniline

A: 583-63-1
ortoquinone

B: 106-51-4
p-benzoquinone

C N2: N2

Conditions

Conditions	Yield
With ammonium metavanadate; sulfuric acid In hydrogenchloride; water for 0.166667h; Product distribution; micro determination;

...Expand

: 108-95-2
phenol

A: 106-41-2
4-bromo-phenol

B: 615-58-7
2,4-dibromophenol

C: 95-56-7
2-hydroxybromobenzene

D: 583-63-1
ortoquinone

E: 120-80-9
benzene-1,2-diol

F: 118-79-6
2,4,6-tribromophenol

G ortho or para-dihydroxybenzene, 2,4-dibromo-1,2-dihydroxybenzene,: ortho or para-dihydroxybenzene, 2,4-dibromo-1,2-dihydroxybenzene,

Conditions

Conditions	Yield
With potassium bromate; sulfuric acid In water at 25℃; for 24h; Product distribution; Mechanism; periodic electrochemical reaction;

...Expand

: 95-47-6
o-xylene

air: air

molybdenum (VI)-oxide /kieselguhr: molybdenum (VI)-oxide /kieselguhr

A: 85-44-9
phthalic anhydride

B: 583-63-1
ortoquinone

C: 15719-64-9, 15719-76-3, 97762-63-5
methylammonium carbonate

Conditions

Conditions	Yield
at 320 - 490℃;

...Expand

: 95-47-6
o-xylene

air: air

vanadium: vanadium

A: 85-44-9
phthalic anhydride

B: 583-63-1
ortoquinone

C: 15719-64-9, 15719-76-3, 97762-63-5
methylammonium carbonate

Conditions

Conditions	Yield
at 320 - 490℃;

...Expand

: 583-63-1
ortoquinone

: 4726-84-5
alanine amide

: 14003-34-0
3-methylquinoxalin-2-ol

Conditions

Conditions	Yield
With sodium hydroxide In methanol Reagent/catalyst; Solvent; Inert atmosphere; Reflux;	93.2%

: 583-63-1
ortoquinone

: 1575-37-7
4-Bromo-benzene-1,2-diamine

: 3331-28-0
2-bromophenazine

Conditions

Conditions	Yield
With sulfuric acid In ethanol at 65℃; for 4h;	92.6%

: 583-63-1
ortoquinone

: 70902-72-6
2-chloro-5-methyl-4-nitroaniline

: 5307-03-9
2-chloro-5-methyl-1,4-phenylenediamine

Conditions

Conditions	Yield
With potassium hydroxide In water	91%

: 583-63-1
ortoquinone

: C56H76N4P2

: C70H84N4O2P2

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;	90.5%

: 583-63-1
ortoquinone

: 120-80-9
benzene-1,2-diol

Conditions

Conditions	Yield
With aluminium(III) iodide In acetonitrile for 1h; Heating;	90%
With sulphurous acid
Rate constant; pH 7.00; reaction with substrate reduced glucose oxidase;

: 583-63-1
ortoquinone

: 80222-96-4
2-aminopropanamide hydrochloride

: 14003-34-0
3-methylquinoxalin-2-ol

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 5h; Inert atmosphere; Reflux;	86%

: 61922-09-6
phosphorohydrazidic acid diisopropyl ester

: 583-63-1
ortoquinone

: C12H19N2O4P

Conditions

Conditions	Yield
In diethyl ether at 25 - 30℃;	85%

: 583-63-1
ortoquinone

: 149-30-4
2-Mercaptobenzothiazole

: 42580-03-0
2-(1,3-benzothiazol-2-ylsulfanyl)benzene-1,4-diol

Conditions

Conditions	Yield
In ethanol at 20℃; for 3h; Addition; reduction;	85%

: 583-63-1
ortoquinone

: [(η5-C5Me5)2U(η2-C2(SiMe3)2)]

: 71-43-2
benzene

: [((η5-C5Me5)2U)2(μ-o-O2C6H4)2]*C6H6

Conditions

Conditions	Yield
Stage #1: ortoquinone; [(η5-C5Me5)2U(η2-C2(SiMe3)2)] In toluene at 20℃; Inert atmosphere; Schlenk technique; Stage #2: benzene Solvent;	84%

...Expand

: 583-63-1
ortoquinone

: 22706-11-2
3-phenyl-4-amino-5-mercapto-1,2,4-triazole

: 5-Phenyl-4-amino-3-(3',4'-dihydroxyphenyl)thio-1,2,4-triazole

Conditions

Conditions	Yield
In ethanol; chloroform at -25℃; for 4h; Addition;	80%

: 72223-17-7
1-trimethylsilyloxy-1,2-diphenylethylene

: 583-63-1
ortoquinone

: 118621-73-1
2-(3,4-Dihydroxy-phenyl)-1,2-diphenyl-ethanone

Conditions

Conditions	Yield
triphenylmethyl perchlorate In dichloromethane at -45℃; 2-3 h;	68%

: 583-63-1
ortoquinone

: 106-49-0
p-toluidine

A: 10551-32-3
(4-methylphenyl)-hydroquinone

B: 30237-07-1
p-tolyl-[1,4]benzoquinone

Conditions

Conditions	Yield
	A 65% B n/a

...Expand

: 1781-78-8
cyclooctyne

: 583-63-1
ortoquinone

: 82274-89-3
Tricyclo<8.2.2.02,9>tetradeca-2(9),13-dien-11,12-dion

Conditions

Conditions	Yield
In chloroform for 12h; 0 deg C to 20 deg C;	63%

: 583-63-1
ortoquinone

: 1394809-62-1
3,6-bis(2-(trimethylsilyl)ethynyl)benzene-1,2-diamine

: 1394809-63-2
1,4-bis((trimethylsilyl)ethynyl)phenazine

Conditions

Conditions	Yield
With acetic acid In ethanol at 40℃; for 16h;	63%

: 583-63-1
ortoquinone

: 24850-33-7
allyltributylstanane

: 1126-61-0
4-allylpyrocatechol

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -78℃;	62%

: 583-63-1
ortoquinone

: 120-80-9
benzene-1,2-diol

: 121-44-8
triethylamine

: triethylammonium tris(ortho-phenylene-1,2-dihydroxy)phosphorate

Conditions

Conditions	Yield
With phosphorous; copper dichloride In benzene for 3.5h; Heating;	60%

...Expand

: 583-63-1
ortoquinone

: 79990-96-8
((1,3-diphenylprop-1-en-2-yl)oxy)trimethylsilane

: 118621-74-2
1-(3,4-Dihydroxy-phenyl)-1,3-diphenyl-propan-2-one

Conditions

Conditions	Yield
triphenylmethyl perchlorate In dichloromethane at -45℃; 2-3 h;	59%

: 642-71-7
3,4,5-trimethoxyphenol

: 583-63-1
ortoquinone

: 3',4'-dihydroxy-1,2,6-trimethoxy-[1,1'-biphenyl]-4(1H)-one

Conditions

Conditions	Yield
Stage #1: 3,4,5-trimethoxyphenol With methylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: ortoquinone In tetrahydrofuran at -40℃; for 0.5h; Inert atmosphere;	59%

: 84-85-5
4-methoxynaphth-1-ol

: 583-63-1
ortoquinone

: 5-methoxynaphtho[1,2-b]benzofuran-8,9-diol

Conditions

Conditions	Yield
Stage #1: 4-methoxynaphth-1-ol With methylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: ortoquinone In tetrahydrofuran at -40℃; for 0.5h; Inert atmosphere;	57%

: 37471-46-8
1-phenyl-1-trimethylsiloxypropene

: 583-63-1
ortoquinone

: 118621-72-0
2-(3,4-Dihydroxy-phenyl)-1-phenyl-propan-1-one

Conditions

Conditions	Yield
triphenylmethyl perchlorate In dichloromethane at -45℃; 2-3 h;	55%

: 583-63-1
ortoquinone

: 4-(furan-2-yl)naphthalen-1-ol

: 5-(furan-2-yl)naphtho[1,2-b]benzofuran-8,9-diol

Conditions

Conditions	Yield
Stage #1: 4-(furan-2-yl)naphthalen-1-ol With methylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: ortoquinone In tetrahydrofuran at -40℃; for 0.5h; Inert atmosphere;	53%

O-Benzoquinone Chemical Properties

IUPAC Name: Cyclohexa-3,5-diene-1,2-dione
Synonyms:1,2-Benzochinon ; 3,5-Cyclohexadiene-1,2-dione ; 3,5-Cyclohexadiene-1,2-dione (9CI) ; Benzo-1,2-quinone
CAS NO:583-63-1
Molecular Formula of O-Benzoquinone (CAS NO.583-63-1) :C₆H₄O₂
Molecular Weight of O-Benzoquinone (CAS NO.583-63-1) :108.0948
Molecular Structure of O-Benzoquinone (CAS NO.583-63-1) :
Surface Tension: 47.8 dyne/cm
Density: 1.256 g/cm³
Flash Point: 76.4 °C
Enthalpy of Vaporization: 44.96 kJ/mol
Boiling Point: 213.3 °C at 760 mmHg
Vapour Pressure: 0.166 mmHg at 25°C
Appearance:It is a red substance soluble in water and insoluble in ethyl ether.

O-Benzoquinone Production

1,2-Benzoquinone is produced on oxidation of catechol exposed to air in aqueous solution or by ortho oxidation of a phenol.

A strain of the bacterium Peudomonas mendocina metabolyzes benzoic acid yielding 1,2-benzoquinone (via cathecol) as the final product.

O-Benzoquinone Toxicity Data With Reference

mmo-sat 100 ng/plate

BECTA6 Bulletin of Environmental Contamination and Toxicology. 24 (1980),590.

O-Benzoquinone Safety Profile

A poison. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

O-Benzoquinone Specification

1,2-Benzoquinone, also cyclohexa-3,5-diene-1,2-dione, is a ketone, with formula C₆H₄O₂. It is one of the two isomers of quinone, the other being 1,4-benzoquinone. 1,2-Benzoquinone is produced on oxidation of catechol or by ortho oxidation of a phenol.

Product Name

2-benzoquinone

Synthetic route

O-Benzoquinone Chemical Properties

O-Benzoquinone Production

O-Benzoquinone Toxicity Data With Reference

O-Benzoquinone Safety Profile

O-Benzoquinone Specification

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