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583-63-1 Usage

Definition

ChEBI: A benzoquinone resulting from the formal oxidation of catechol.

Safety Profile

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

Check Digit Verification of cas no

The CAS Registry Mumber 583-63-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 3 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 583-63:
(5*5)+(4*8)+(3*3)+(2*6)+(1*3)=81
81 % 10 = 1
So 583-63-1 is a valid CAS Registry Number.

583-63-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2-benzoquinone

1.2 Other means of identification

Product number -
Other names 1,2-Benzoquinone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:583-63-1 SDS

583-63-1Synthetic route

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

benzene-1,2-diol

ortoquinone
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%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

ortoquinone
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%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

ortoquinone
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
2-amino-phenol
95-55-6

2-amino-phenol

ortoquinone
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;
3-hydroxy-2-phenyl-1H-inden-1-one
13031-53-3

3-hydroxy-2-phenyl-1H-inden-1-one

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

benzene-1,2-diol

A

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

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

B

ortoquinone
583-63-1

ortoquinone

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

di-tert-butyliminoxyl

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

benzene-1,2-diol

ortoquinone
583-63-1

ortoquinone

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

phenol

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

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

A

ortoquinone
583-63-1

ortoquinone

B

2-methoxy-phenol
90-05-1

2-methoxy-phenol

C

Veratric acid
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%
benzo[1,4]dioxine
255-37-8

benzo[1,4]dioxine

A

ortoquinone
583-63-1

ortoquinone

B

benzene-1,2-diol
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
2,9,11,12,13-Pentaoxa-tricyclo[8.2.1.03,8]trideca-3,5,7-triene
110851-16-6

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

A

ortoquinone
583-63-1

ortoquinone

B

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

benzene-1,2-diol

Conditions
ConditionsYield
In dichloromethane at -78℃; for 1h; Irradiation;A 29%
B 51%
salicylic alcohol
90-01-7

salicylic alcohol

A

ortoquinone
583-63-1

ortoquinone

B

3-hydroxymethyl-o-benzoquinone

3-hydroxymethyl-o-benzoquinone

C

salicylaldehyde
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%
1,2-benzosemiquinone anion radical
19021-48-8

1,2-benzosemiquinone anion radical

A

ortoquinone
583-63-1

ortoquinone

B

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

benzene-1,2-diol

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

benzene

ortoquinone
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;
phenol
108-95-2

phenol

A

ortoquinone
583-63-1

ortoquinone

B

p-benzoquinone
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.
benzene
71-43-2

benzene

A

ortoquinone
583-63-1

ortoquinone

B

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

benzene-1,2-diol

C

hydroquinone
123-31-9

hydroquinone

D

p-benzoquinone
106-51-4

p-benzoquinone

E

phenol
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;
phenol
108-95-2

phenol

A

ortoquinone
583-63-1

ortoquinone

B

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

benzene-1,2-diol

C

hydroquinone
123-31-9

hydroquinone

D

p-benzoquinone
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;
ethyl 2-diazo-3-oxo-3-phenylpropanoate
28383-65-5

ethyl 2-diazo-3-oxo-3-phenylpropanoate

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

benzene-1,2-diol

A

ortoquinone
583-63-1

ortoquinone

B

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

ethyl 3-oxo-3-phenylpropionate

Conditions
ConditionsYield
copper In benzene Oxidation;
water
7732-18-5

water

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

benzene-1,2-diol

Ce(SO4)2

Ce(SO4)2

ortoquinone
583-63-1

ortoquinone

diethyl ether
60-29-7

diethyl ether

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

benzene-1,2-diol

silver oxide

silver oxide

ortoquinone
583-63-1

ortoquinone

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

benzene-1,2-diol

A

ortoquinone
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.);
anthranilic acid
118-92-3

anthranilic acid

A

ortoquinone
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;
meta-aminobenzoic acid
99-05-8

meta-aminobenzoic acid

A

ortoquinone
583-63-1

ortoquinone

B

p-benzoquinone
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;
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

ortoquinone
583-63-1

ortoquinone

B

N2

N2

Conditions
ConditionsYield
With ammonium metavanadate; sulfuric acid In hydrogenchloride; water for 0.25h; Product distribution; micro determination;
2-amino-phenol
95-55-6

2-amino-phenol

A

ortoquinone
583-63-1

ortoquinone

B

N2

N2

Conditions
ConditionsYield
With ammonium metavanadate; sulfuric acid In hydrogenchloride; water for 0.166667h; Product distribution; micro determination;
m-phenylenediamine
108-45-2

m-phenylenediamine

A

ortoquinone
583-63-1

ortoquinone

B

p-benzoquinone
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;
m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

A

ortoquinone
583-63-1

ortoquinone

B

p-benzoquinone
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;
phenol
108-95-2

phenol

A

4-bromo-phenol
106-41-2

4-bromo-phenol

B

2,4-dibromophenol
615-58-7

2,4-dibromophenol

C

2-hydroxybromobenzene
95-56-7

2-hydroxybromobenzene

D

ortoquinone
583-63-1

ortoquinone

E

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

benzene-1,2-diol

F

2,4,6-tribromophenol
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;
o-xylene
95-47-6

o-xylene

air

air

molybdenum (VI)-oxide /kieselguhr

molybdenum (VI)-oxide /kieselguhr

A

phthalic anhydride
85-44-9

phthalic anhydride

B

ortoquinone
583-63-1

ortoquinone

C

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

methylammonium carbonate

Conditions
ConditionsYield
at 320 - 490℃;
o-xylene
95-47-6

o-xylene

air

air

vanadium

vanadium

A

phthalic anhydride
85-44-9

phthalic anhydride

B

ortoquinone
583-63-1

ortoquinone

C

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

methylammonium carbonate

Conditions
ConditionsYield
at 320 - 490℃;
ortoquinone
583-63-1

ortoquinone

alanine amide
4726-84-5

alanine amide

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

3-methylquinoxalin-2-ol

Conditions
ConditionsYield
With sodium hydroxide In methanol Reagent/catalyst; Solvent; Inert atmosphere; Reflux;93.2%
ortoquinone
583-63-1

ortoquinone

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

4-Bromo-benzene-1,2-diamine

2-bromophenazine
3331-28-0

2-bromophenazine

Conditions
ConditionsYield
With sulfuric acid In ethanol at 65℃; for 4h;92.6%
ortoquinone
583-63-1

ortoquinone

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

2-chloro-5-methyl-4-nitroaniline

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

2-chloro-5-methyl-1,4-phenylenediamine

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

ortoquinone

C56H76N4P2

C56H76N4P2

C70H84N4O2P2

C70H84N4O2P2

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

ortoquinone

benzene-1,2-diol
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;
ortoquinone
583-63-1

ortoquinone

2-aminopropanamide hydrochloride
80222-96-4

2-aminopropanamide hydrochloride

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

3-methylquinoxalin-2-ol

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

phosphorohydrazidic acid diisopropyl ester

ortoquinone
583-63-1

ortoquinone

C12H19N2O4P

C12H19N2O4P

Conditions
ConditionsYield
In diethyl ether at 25 - 30℃;85%
ortoquinone
583-63-1

ortoquinone

2-Mercaptobenzothiazole
149-30-4

2-Mercaptobenzothiazole

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

2-(1,3-benzothiazol-2-ylsulfanyl)benzene-1,4-diol

Conditions
ConditionsYield
In ethanol at 20℃; for 3h; Addition; reduction;85%
ortoquinone
583-63-1

ortoquinone

[(η5-C5Me5)2U(η2-C2(SiMe3)2)]

[(η5-C5Me5)2U(η2-C2(SiMe3)2)]

benzene
71-43-2

benzene

[((η5-C5Me5)2U)2(μ-o-O2C6H4)2]*C6H6

[((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%
ortoquinone
583-63-1

ortoquinone

3-phenyl-4-amino-5-mercapto-1,2,4-triazole
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

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

Conditions
ConditionsYield
In ethanol; chloroform at -25℃; for 4h; Addition;80%
1-trimethylsilyloxy-1,2-diphenylethylene
72223-17-7

1-trimethylsilyloxy-1,2-diphenylethylene

ortoquinone
583-63-1

ortoquinone

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

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

Conditions
ConditionsYield
triphenylmethyl perchlorate In dichloromethane at -45℃; 2-3 h;68%
ortoquinone
583-63-1

ortoquinone

p-toluidine
106-49-0

p-toluidine

A

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

(4-methylphenyl)-hydroquinone

B

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

p-tolyl-[1,4]benzoquinone

Conditions
ConditionsYield
A 65%
B n/a
cyclooctyne
1781-78-8

cyclooctyne

ortoquinone
583-63-1

ortoquinone

Tricyclo<8.2.2.02,9>tetradeca-2(9),13-dien-11,12-dion
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%
ortoquinone
583-63-1

ortoquinone

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

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

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

1,4-bis((trimethylsilyl)ethynyl)phenazine

Conditions
ConditionsYield
With acetic acid In ethanol at 40℃; for 16h;63%
ortoquinone
583-63-1

ortoquinone

allyltributylstanane
24850-33-7

allyltributylstanane

4-allylpyrocatechol
1126-61-0

4-allylpyrocatechol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at -78℃;62%
ortoquinone
583-63-1

ortoquinone

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

benzene-1,2-diol

triethylamine
121-44-8

triethylamine

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

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

Conditions
ConditionsYield
With phosphorous; copper dichloride In benzene for 3.5h; Heating;60%
ortoquinone
583-63-1

ortoquinone

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

((1,3-diphenylprop-1-en-2-yl)oxy)trimethylsilane

1-(3,4-Dihydroxy-phenyl)-1,3-diphenyl-propan-2-one
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%
3,4,5-trimethoxyphenol
642-71-7

3,4,5-trimethoxyphenol

ortoquinone
583-63-1

ortoquinone

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

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

4-methoxynaphth-1-ol

ortoquinone
583-63-1

ortoquinone

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

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%
1-phenyl-1-trimethylsiloxypropene
37471-46-8

1-phenyl-1-trimethylsiloxypropene

ortoquinone
583-63-1

ortoquinone

2-(3,4-Dihydroxy-phenyl)-1-phenyl-propan-1-one
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%
ortoquinone
583-63-1

ortoquinone

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

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

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

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%

583-63-1Relevant articles and documents

Kinetic characterization of the oxidation of chlorogenic acid by polyphenol oxidase and peroxidase. Characteristics of the o-quinone

Munoz,Garcia-Molina,Varon,Rodriguez-Lopez,Garcia-Ruiz,Garcia-Canovas,Tudela

, p. 920 - 928 (2007)

Chlorogenic acid is the major diphenol of many fruits, where it is oxidized enzymatically by polyphenol oxidase (PPO) or peroxidase (POD) to its o-quinone. In spectrophotometric studies of chlorogenic acid oxidation with a periodate ratio of [CGA]0/[lO4-]0 0/[IO4-]0 > 1, the o-quinone was characterized as follows: λmax at 400 nm and ε = 2000 and 2200 M-1 cm-1 at pH 4.5 and 7.0, respectively. In studies of o-quinone generated by the oxidation of chlorogenic acid using a periodate at ratio of [CGA]0/[lO4-]0 > 1, a reaction with the remaining substrate was detected, showing rate constants of k = 2.73 ± 0.17 M-1 s-1 and k = 0.05 ± 0.01 M-1 s-1 at the above pH values. A Chronometric spectrophotometric method is proposed to kinetically characterize the action of the PPO or POD on the basis of measuring the time it takes for a given amount of ascorbic acid to be consumed in the reaction with the o-quinone. The kinetic constants of mushroom PPO and horseradish POD are determined.

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Dawson,Nelson

, p. 245,246 (1938)

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Mentasti et al.

, p. 537,539-540 (1975)

Alzheimer's disease related copper(II)-β-amyloid peptide exhibits phenol monooxygenase and catechol oxidase activities

Da Silva, Giordano F. Z.,Ming, Li-June

, p. 5501 - 5504 (2005)

(Chemical Equation Presented) A gray area in gray matter: The Cu II complex of a truncated β-amyloid, CuAβ1-20, catalyzes the oxidation of catechol and the hydroxylation and oxidation of phenol (see picture) with dramatic rate accelerations (≈ 10 5-106-fold increases). The Cu-oxygen chemistry of CuAβ may offer both a better understanding of the chemical effect in the brains of patients who suffer from Alzheimer's disease as well as possible treatment strategies of this disease.

How well should the active site and the specific recognition be defined for proficient catalysis? - Effective and cooperative polyphenol/catechol oxidation and oxidative dna cleavage by a copper(II)-binding and H-bonding copolymer

Lykourinou, Vasiliki,Hanafy, Ahmed I.,Da Silva, Giordano F. Z.,Bisht, Kirpal S.,Larsen, Randy W.,Livingston, Brian T.,Angerhofer, Alexander,Ming, Li-June

, p. 2584 - 2592 (2008)

Despite the mainly inhomogeneous and unstructured nature of linear polymers, the CuII complex of a vinylpyridine-acrylamide copolymer exhibits very efficient 2-electron catalysis toward the oxidation of catechol and derivatives to form quinones with and without 80 mM (0.27%) H 2O2, showing remarkable (0.114-2.67) × 10 5 and (2.83-9.60) × 104-fold rate enhancements, respectively, in terms of first-order rate constant relative to auto-oxidation of the substrates in an aqueous environment under mild conditions. Metal-binding profiles suggest the presence of cooperativity in the catalysis. The oxidation catalysis is inhibited by the di-copper tyrosinase specific kojic acid. Moreover, electron paramagnetic resonance spectra reveal magnetic interaction of the CuII ions. On the basis of the results, the catalysis by this CuII-polymer seems to be consistent with the mechanism of type-3 di-copper oxidases. This complex also shows effective single- and double-stranded DNA cleavage in the presence of 1.0% H2O2. These studies suggest this CuII-polymer complex can serve as a unique chemical nuclease and a versatile chemical system for further exploration of Cu-oxygen chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Pyridinium Chlorochromate Supported on Montmorillonite–KSF as a Versatile Oxidant under Ball Milling Conditions

Hosseinzadeh, Rahman,Narimani, Erfan,Mavvaji, Mohammad

, p. 461 - 471 (2021/08/09)

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Dearomatization of Electron-Deficient Phenols to ortho-Quinones: Bidentate Nitrogen-Ligated Iodine(V) Reagents

Xiao, Xiao,Greenwood, Nathaniel S.,Wengryniuk, Sarah E.

supporting information, p. 16181 - 16187 (2019/11/05)

Despite their broad utility, the synthesis of ortho-quinones remains a significant challenge, in particular, access to electron-deficient derivatives remains an unsolved problem. Reported here is the first general method for the synthesis of electron-deficient ortho-quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen-ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)-HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho-quinone products was examined, resulting in a facile one-pot synthesis of catechols, as well as the incorporation of a variety of heteroatom nucleophiles. This method represents the first synthetic application of Bi(N)-HVIs and demonstrates their potential as a platform for the further development of highly reactive, but also highly tunable, I(V) reagents.

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