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O-Benzoquinone

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Name

O-Benzoquinone

EINECS N/A
CAS No. 583-63-1 Density 1.256g/cm3
PSA 34.14000 LogP 0.25060
Solubility N/A 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 N/A Appearance N/A
Safety A poison. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. Risk Codes N/A
Molecular Structure Molecular Structure of 583-63-1 (2-benzoquinone) Hazard Symbols N/A
Synonyms

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

Article Data 89

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%

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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