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O-Benzoquinone

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Name

O-Benzoquinone

EINECS
CAS No. 583-63-1 Density 1.256g/cm3
PSA 34.14000 LogP 0.25060
Solubility Melting Point 65°C (rough estimate)
Formula C6H4 O2 Boiling Point 213.3°Cat760mmHg
Molecular Weight 108.10 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 Molecular Structure of 583-63-1 (3,5-Cyclohexadiene-1,2-dione) Hazard Symbols
Synonyms

o-Benzoquinone(8CI); 1,2-Benzoquinone; o-Quinone

 

O-Benzoquinone Synthetic route

120-80-9

benzene-1,2-diol

583-63-1

ortoquinone

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium acetate In water; acetonitrile Electrochemical reaction;A 90%
B n/a
33802-06-1

di-tert-butyliminoxyl

120-80-9

benzene-1,2-diol

583-63-1

ortoquinone

Conditions
ConditionsYield
at -30℃;80%
108-95-2

phenol

583-63-1

ortoquinone

Conditions
ConditionsYield
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
ConditionsYield
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; methanol at 70℃; for 4h; pH=10;A 22%
B 17%
C 71%
255-37-8

benzo[1,4]dioxine

A

583-63-1

ortoquinone

B

120-80-9

benzene-1,2-diol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
19021-48-8

1,2-benzosemiquinone anion radical

A

583-63-1

ortoquinone

B

120-80-9

benzene-1,2-diol

Conditions
ConditionsYield
With sodium azide; phosphate buffer; dinitrogen monoxide In water Mechanism; Rate constant; Irradiation;
71-43-2

benzene

583-63-1

ortoquinone

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With pyridine; oxygen; iron(III) octaethyl porphirin In ethanol at 24.9℃; under 760 Torr; Product distribution; Mechanism; Irradiation; var. of catalyst, base, pH;
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
ConditionsYield
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;
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
ConditionsYield
copper In benzene Oxidation;
120-80-9

benzene-1,2-diol

Ce(SO4)2

Ce(SO4)2

583-63-1

ortoquinone

60-29-7

diethyl ether

120-80-9

benzene-1,2-diol

silver oxide

silver oxide

583-63-1

ortoquinone

120-80-9

benzene-1,2-diol

A

583-63-1

ortoquinone

B

24-

24-

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With ammonium metavanadate; sulfuric acid In hydrogenchloride; water for 0.333333h; Product distribution; micro determination;
95-54-5

1,2-diamino-benzene

A

583-63-1

ortoquinone

B

N2

N2

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With ammonium metavanadate; sulfuric acid In hydrogenchloride; water for 0.25h; Product distribution; micro determination;
591-27-5

m-Hydroxyaniline

A

583-63-1

ortoquinone

B

106-51-4

p-benzoquinone

C

N2

N2

Conditions
ConditionsYield
With ammonium metavanadate; sulfuric acid In hydrogenchloride; water for 0.166667h; Product distribution; micro determination;
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
ConditionsYield
With potassium bromate; sulfuric acid In water at 25℃; for 24h; Product distribution; Mechanism; periodic electrochemical reaction;
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
ConditionsYield
at 320 - 490℃;
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
ConditionsYield
at 320 - 490℃;
583-63-1

ortoquinone

4726-84-5

alanine amide

14003-34-0

3-methylquinoxalin-2-ol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With potassium hydroxide In water91%
583-63-1

ortoquinone

C56H76N4P2

C70H84N4O2P2

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;90.5%
583-63-1

ortoquinone

120-80-9

benzene-1,2-diol

Conditions
ConditionsYield
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
ConditionsYield
With potassium hydroxide In tetrahydrofuran for 5h; Inert atmosphere; Reflux;86%
61922-09-6

phosphorohydrazidic acid diisopropyl ester

583-63-1

ortoquinone

C12H19N2O4P

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
Stage #1: ortoquinone; [(η5-C5Me5)2U(η2-C2(SiMe3)2)] In toluene at 20℃; Inert atmosphere; Schlenk technique;
Stage #2: benzene Solvent;
84%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
A 65%
B n/a
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
ConditionsYield
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
ConditionsYield
With acetic acid In ethanol at 40℃; for 16h;63%
583-63-1

ortoquinone

24850-33-7

allyltributylstanane

1126-61-0

4-allylpyrocatechol

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

1.    

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.

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