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| CAS No.: | 583-63-1 |
|---|---|
| Name: | 2-benzoquinone |
| Article Data: | 89 |
| Molecular Structure: | |
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| Formula: | C6H4 O2 |
| Molecular Weight: | 108.097 |
| Synonyms: | o-Benzoquinone(8CI); 1,2-Benzoquinone; o-Quinone |
| Density: | 1.256g/cm3 |
| Melting Point: | 65°C (rough estimate) |
| Boiling Point: | 213.3°Cat760mmHg |
| Flash Point: | 76.4°C |
| Safety: | A poison. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. |
| PSA: | 34.14000 |
| LogP: | 0.25060 |
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| 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% |
| 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% |
| 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 |
| 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; |
| Conditions | Yield |
|---|---|
| With sodium acetate In water; acetonitrile Electrochemical reaction; | A 90% B n/a |
| Conditions | Yield |
|---|---|
| at -30℃; | 80% |
| 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 | Yield |
|---|---|
| With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; methanol at 70℃; for 4h; pH=10; | A 22% B 17% C 71% |
| 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 | Yield |
|---|---|
| In dichloromethane at -78℃; for 1h; Irradiation; | A 29% B 51% |
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Chemistry
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) :.png)
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.
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.
Toxicity Data With Reference
| 1. | mmo-sat 100 ng/plate | BECTA6 Bulletin of Environmental Contamination and Toxicology. 24 (1980),590. |
Safety Profile
A poison. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
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.