Welcome to LookChem.com Sign In|Join Free

CAS

  • or

120-80-9

Post Buying Request

120-80-9 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

120-80-9 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 120-80-9 differently. You can refer to the following data:
1. Off-white powder
2. Catechol is a white crystalline solid. Turns brown on contact with light and air.

Uses

Different sources of media describe the Uses of 120-80-9 differently. You can refer to the following data:
1. Pyrocatechol is used in photography, in dyeing fur, and as a topical antiseptic.
2. In photography; dyeing fur; as reagent.
3. In the manufacture of rubber antioxidants and monomer inhibitors to stop radical polymerization; in dyes, as a photographic developer; in formulations for pharmaceuticals, perfumes, inks, and insecticides

Production Methods

Pyrocatechol may be obtained by the fusion of o-phenolsulfonic acid with alkali, by heating chorophenol with a solution of sodium hydroxide at 200°C in an autoclave, or by cleavage of the methyl ether group of guaiacol (obtained from beechwood tar) with hydriodic acid.

Definition

A colourless crystalline PHENOL containing two hydroxyl groups. It is used in photographic developing.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 4275, 1980 DOI: 10.1021/jo01310a003

General Description

Solid; white; odorless. Sinks and mixes with water.

Air & Water Reactions

Turns brown on exposure to air and light, especially when moist. Water soluble. Aqueous solutions soon turn brown on exposure to air and light.

Reactivity Profile

POISONOUS GASES MAY BE PRODUCED WHEN HEATED. Pyrocatechol may form toxic fumes at high temperatures. [USCG, 1999]. Pyrocatechol can react with acid chlorides, acid anhydrides, bases and oxidizing agents. Pyrocatechol reacts violently on contact with concentrated nitric acid. Pyrocatechol acts as a reducing agent .

Hazard

Strong irritant. Toxic by skin absorption. Eye and upper respiratory tract irritant, and der- matitis. Possible carcinogen.

Health Hazard

Different sources of media describe the Health Hazard of 120-80-9 differently. You can refer to the following data:
1. DUST: Irritating to eyes, nose and throat. If inhaled will cause coughing or difficult breathing. SOLID: Will burn skin and eyes. Harmful if swallowed.
2. Acute oral and percutaneous toxicity of pyrocatechol is greater than that of phenol; inhalation toxicity is less than that of phenol. The toxic symptoms include weakness, muscular pain, dark urine, tremor, dyspnea, and convulsions. Large amounts can produce degenerative changes in renal tubules. Large doses can cause death due to respiratory failure. Skin contact can cause eczematous dermatitis.LD50 value, oral (rats): 260 mg/kg LD50 value, skin (rabbits): 800 mg/kg.

Fire Hazard

Combustible. POISONOUS GASES MAY BE PRODUCED WHEN HEATED. May form toxic fumes at high temperatures.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by ingestion, subcutaneous, intraperitoneal, intravenous, and parenteral routes. Moderately toxic by skin contact. Experimental reproductive effects. Can cause dermatitis on skin contact. An allergen. Human mutation data reported. Questionable carcinogen. Systemic effects sirmlar to those of phenol. Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. Hypergolic reaction with concentrated nitric acid. To fight fire, use water, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also PHENOL.

Potential Exposure

Used as a chemical intermediate; pharmaceutical and veterinary drug; as an antiseptic; in photography; in dyestuff manufacture and application. It is also used in electroplating, in the formulation of specialty inks; in antioxidants; and light stabilizers.

Carcinogenicity

Pyrocatechol has been extensively studied for its role in carcinogenesis of the rat glandular stomach; it was concluded that pyrocatechol is carcinogenic. When rats and mice were administered 0.8% pyrocatechol in their feed for life, there was an increase in glandular stomach adenocarcinoma in both male and female rats. Pyrocatechol also caused hyperplasia of the glandular stomach in both rats and mice, a mechanism that could cause promotion of carcinogen-initiated cells; no effects on the esophagus or urinary bladder were reported. There were no cutaneous neoplasms when pyrocatechol was applied in dermal studies. Pyrocatechol may be classified as a cocarcinogen because it enhanced the number and/or incidence of lesions in the stomach induced by several carcinogenic nitrosamines and cutaneous neoplasms when administered dermally together with several carcinogens.

Shipping

UN 2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Crystallise catechol from *benzene or toluene and sublime it in vacuo. [Rozo et al. Anal Chem 58 2988 1986, Beilstein 6 IV 5557.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Check Digit Verification of cas no

The CAS Registry Mumber 120-80-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 0 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 120-80:
(5*1)+(4*2)+(3*0)+(2*8)+(1*0)=29
29 % 10 = 9
So 120-80-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H

120-80-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A10164)  Catechol, 99%   

  • 120-80-9

  • 250g

  • 187.0CNY

  • Detail
  • Alfa Aesar

  • (A10164)  Catechol, 99%   

  • 120-80-9

  • 1000g

  • 524.0CNY

  • Detail
  • Alfa Aesar

  • (A10164)  Catechol, 99%   

  • 120-80-9

  • 5000g

  • 1837.0CNY

  • Detail
  • Sigma-Aldrich

  • (430749)  Pyrocatechol  purified by sublimation, ≥99.5%

  • 120-80-9

  • 430749-5G

  • 730.08CNY

  • Detail

120-80-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name catechol

1.2 Other means of identification

Product number -
Other names 1,2-dihydroxybenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Catechol is used as a photographic developer, a developer for fur dyes, as an intermediate for antioxidants in rubber and lubricating oils, in polymerization inhibitors, and in pharmaceuticals.
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:120-80-9 SDS

120-80-9Synthetic route

phenol
108-95-2

phenol

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

benzene-1,2-diol

Conditions
ConditionsYield
With dihydrogen peroxide; MgAlZr0.1-HT In Petroleum ether at 79.9℃; for 8h;100%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In methanol; chloroform at -25℃; for 0.333333h;97%
With tert.-butylhydroperoxide In water; acetonitrile at 70℃; for 6h; Catalytic behavior; Temperature; Solvent;89%
1,3-benzodioxol-2-one
2171-74-6

1,3-benzodioxol-2-one

isopropyl alcohol
67-63-0

isopropyl alcohol

A

bis-2-propyl carbonate
6482-34-4

bis-2-propyl carbonate

B

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

benzene-1,2-diol

Conditions
ConditionsYield
With sodium methylate In neat (no solvent) at 100℃; under 1500.15 Torr; for 5h; Inert atmosphere; Autoclave;A 67%
B 100%
With sodium methylate at 100℃; for 5h; Temperature; Autoclave; Inert atmosphere;A 90 %Chromat.
B n/a
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

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

benzene-1,2-diol

Conditions
ConditionsYield
With 1,3-dimethyl-2-imidazolidinone; sodium hexamethyldisilazane In tetrahydrofuran at 185℃; for 12h; further reagent: LDA;99%
With sodium di(ethyl)amine In N,N,N,N,N,N-hexamethylphosphoric triamide; benzene for 12h; Heating;85%
With aluminium(III) iodide In carbon disulfide for 7h; Heating; Var. solvent, time and substrate reagent ratio;80%
2-methoxy-phenol
90-05-1

2-methoxy-phenol

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

benzene-1,2-diol

Conditions
ConditionsYield
Stage #1: 2-methoxy-phenol With pyridine; iodine; aluminium In acetonitrile for 18h; Reflux;
Stage #2: With hydrogenchloride In water; acetonitrile at 20℃;
99%
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Autoclave; Inert atmosphere; Green chemistry;97%
With aluminium(III) iodide; calcium oxide In acetonitrile at 80℃; for 18h; Reagent/catalyst;94%
2,2-dimethyl-1,3-benzodioxole
14005-14-2

2,2-dimethyl-1,3-benzodioxole

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

benzene-1,2-diol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 18h; Catalytic behavior; Reagent/catalyst; Solvent;99%
With indium(III) triflate In water; acetonitrile at 120℃; for 0.5h; Microwave irradiation;91%
With sodium di(ethyl)amine In N,N,N,N,N,N-hexamethylphosphoric triamide; benzene for 12h; Heating;88%
6H,11H-dibenzo<14>dioxocin
116915-91-4

6H,11H-dibenzo<14>dioxocin

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

benzene-1,2-diol

Conditions
ConditionsYield
With hydrogen; palladium hydroxide - carbon In ethanol under 760 Torr;99%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

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

benzene-1,2-diol

Conditions
ConditionsYield
With glycolic Acid; copper hydroxide; sodium hydroxide In water; dimethyl sulfoxide at 120℃; for 6h; Inert atmosphere; Schlenk technique;99%
With β-D-glucose; copper(II) acetate monohydrate; potassium hydroxide In water; dimethyl sulfoxide at 20 - 120℃; for 16h;83%
salicylaldehyde
90-02-8

salicylaldehyde

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

benzene-1,2-diol

Conditions
ConditionsYield
With dihydrogen peroxide at 20℃; for 0.666667h; Time; Dakin Phenol Oxidation; Green chemistry;98%
With dihydrogen peroxide In water at 20℃; for 2h; Dakin Phenol Oxidation; Green chemistry;98%
With 7,8-difluoro-1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine; dihydrogen peroxide; sodium hydrogencarbonate In methanol; water at 20℃; for 1h; Dakin oxidation;92%
1,2-bis(trimethylsilyloxy)benzene
5075-52-5

1,2-bis(trimethylsilyloxy)benzene

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

benzene-1,2-diol

Conditions
ConditionsYield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;98%
2-ethoxyanisole
17600-72-5

2-ethoxyanisole

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

benzene-1,2-diol

Conditions
ConditionsYield
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Autoclave; Inert atmosphere; Green chemistry;98%
With water; hydrogen bromide; Aliquat 336 at 105℃; for 9h; Catalytic behavior;72%
1,2-dimethoxybenzene
91-16-7

1,2-dimethoxybenzene

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

benzene-1,2-diol

Conditions
ConditionsYield
With 1,3-dimethyl-2-imidazolidinone; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 185℃; for 12h;97%
With hydrogen iodide at 25℃; for 24h; Inert atmosphere;96%
With aluminium(III) iodide In acetonitrile for 0.5h; Heating; Var. solvent, time and substrate reagent ratio;93%
1-(4-hydroxy-3-methoxyphenyl)propan-1-ol
6997-34-8

1-(4-hydroxy-3-methoxyphenyl)propan-1-ol

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

benzene-1,2-diol

Conditions
ConditionsYield
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Sealed tube; Inert atmosphere;97%
2-Iodophenol
533-58-4

2-Iodophenol

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

benzene-1,2-diol

Conditions
ConditionsYield
With copper(l) iodide; 8-quinolinol; potassium hydroxide In water; dimethyl sulfoxide; tert-butyl alcohol at 100℃; for 48h; Inert atmosphere;95%
Stage #1: 2-Iodophenol With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In water; dimethyl sulfoxide at 20 - 100℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; Inert atmosphere;
86%
With basolite C300; potassium hydroxide In water; dimethyl sulfoxide at 125℃; for 12h;84%
2-Ethoxyphenol
94-71-3

2-Ethoxyphenol

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

benzene-1,2-diol

Conditions
ConditionsYield
With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 18h;95%
With aluminium(III) iodide; dimethyl sulfoxide In acetonitrile at 80℃; for 18h;95%
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h;72%
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h;72%
With oxygen; copper(II) perchlorate; ascorbic acid In water; acetone at 60℃; for 20h;25%
2-allyloxyphenol
1126-20-1

2-allyloxyphenol

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

benzene-1,2-diol

Conditions
ConditionsYield
With boron dimethyl-trifluoro sulphide In dichloromethane at 0℃; for 0.0833333h;95%
2-hydroxyphenyl boronic acid
89466-08-0

2-hydroxyphenyl boronic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

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

benzene-1,2-diol

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;95%
2-(2-phenylethoxy)phenol
33130-24-4

2-(2-phenylethoxy)phenol

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

benzene-1,2-diol

Conditions
ConditionsYield
With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 18h;95%
With aluminium(III) iodide; dimethyl sulfoxide In acetonitrile at 80℃; for 18h;95%
With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 18h;93%
N-(phenoxy)acetamide
5661-50-7

N-(phenoxy)acetamide

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

benzene-1,2-diol

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; malonic acid In methanol at 25℃; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;95%
2-Isopropoxyphenol
4812-20-8

2-Isopropoxyphenol

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

benzene-1,2-diol

Conditions
ConditionsYield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;94%
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;94%
With aluminium(III) iodide; calcium oxide In acetonitrile at 80℃; for 18h;94%
2-bromo-6-hydroxycyclohex-2-en-1-one

2-bromo-6-hydroxycyclohex-2-en-1-one

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

benzene-1,2-diol

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene93%
O-benzylcatechol
6272-38-4

O-benzylcatechol

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

benzene-1,2-diol

Conditions
ConditionsYield
With aluminium(III) iodide; dimethyl sulfoxide In acetonitrile at 80℃; for 18h;93%
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h;63%
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h;63%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

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

benzene-1,2-diol

Conditions
ConditionsYield
With Na-X zeolite In water at 200℃; for 1h; Autoclave;91%
With Cocos nucifera juice at 20℃; for 48h; Inert atmosphere;88%
With cucumber juice at 30 - 35℃; for 48h; Inert atmosphere; Green chemistry;85%
4-tert-Butylcatechol
98-29-3

4-tert-Butylcatechol

A

4-tert-butyltoluene
98-51-1

4-tert-butyltoluene

B

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

benzene-1,2-diol

Conditions
ConditionsYield
With Nafion-H; toluene for 2h; Heating;A 97 % Chromat.
B 91%
4-tert-Butylcatechol
98-29-3

4-tert-Butylcatechol

toluene
108-88-3

toluene

A

4-tert-butyltoluene
98-51-1

4-tert-butyltoluene

B

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

benzene-1,2-diol

Conditions
ConditionsYield
With Nafion-H for 2h; Heating;A 97 % Chromat.
B 91%
4-oxo-cyclohexyl 2,2-dimethylpropanoate
165105-99-7

4-oxo-cyclohexyl 2,2-dimethylpropanoate

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

benzene-1,2-diol

Conditions
ConditionsYield
With iodine; oxygen; dimethyl sulfoxide at 80℃; for 12h;91%
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;
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

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

benzene-1,2-diol

Conditions
ConditionsYield
With sodium percarbonate In tetrahydrofuran; water; N,N-dimethyl-formamide for 8h; ultrasonication;90%
With sulfuric acid; dihydrogen peroxide; boric acid In tetrahydrofuran; water at 20℃; for 36h; Oxidation;90%
1-acetoxy-6-oxocyclohexa-2,4-dienyl propanoate
75724-54-8

1-acetoxy-6-oxocyclohexa-2,4-dienyl propanoate

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

benzene-1,2-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 1h; Heating;90%
3,4-dihydro-2H-benzo[b][1,4]dioxepine
7216-18-4

3,4-dihydro-2H-benzo[b][1,4]dioxepine

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

benzene-1,2-diol

Conditions
ConditionsYield
With aluminum (III) chloride In benzene for 4h; Solvent; Time; Temperature; Reflux;90%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

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

1,2-diamino-benzene

Phenazin
92-82-0

Phenazin

Conditions
ConditionsYield
In water at 210℃; for 0.25h; Microwave irradiation;100%
at 200℃;
at 200 - 210℃; in geschlossenen Rohr;
With potassium dichromate; acetic acid for 24h; Reflux;
benzene-1,2-diol
120-80-9

benzene-1,2-diol

phenylboronic acid
98-80-6

phenylboronic acid

2-phenyl-1,3,2-benzodioxaborole
5747-23-9

2-phenyl-1,3,2-benzodioxaborole

Conditions
ConditionsYield
at 80℃; for 1h;100%
for 0.166667h; Schlenk technique;96%
In dichloromethane; ethyl acetate at 20℃;81%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

1-bromo-3,4-dihydroxybenzene
17345-77-6

1-bromo-3,4-dihydroxybenzene

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 3.5h; Heating;100%
With tetrafluoroboric acid diethyl ether; N-Bromosuccinimide In acetonitrile at -30 - 20℃;100%
With N-Bromosuccinimide; tetrafluoroboric acid In diethyl ether; acetonitrile regioselective reaction;100%
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%
dichloromethylenedimethyliminium chloride
33842-02-3, 529510-96-1

dichloromethylenedimethyliminium chloride

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

benzene-1,2-diol

Benzo[1,3]dioxol-2-ylidene-dimethyl-ammonium; chloride
36156-21-5

Benzo[1,3]dioxol-2-ylidene-dimethyl-ammonium; chloride

Conditions
ConditionsYield
at -20℃; for 1h; ball mill;100%
In dichloromethane for 1h; Heating;
benzene-1,2-diol
120-80-9

benzene-1,2-diol

1-dodecylbromide
143-15-7

1-dodecylbromide

1,2-bisdodecyloxybenzene
42244-53-1

1,2-bisdodecyloxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetone for 48h; Williamson ether synthesis; Reflux;100%
With potassium carbonate In acetone for 48h; Heating;95%
With potassium carbonate; potassium iodide In acetone for 48h; Reflux;95%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

ethyl bromoacetate
105-36-2

ethyl bromoacetate

ethyl 2-<2-<(ethoxycarbonyl)methoxy>phenoxy>acetate
52376-09-7

ethyl 2-<2-<(ethoxycarbonyl)methoxy>phenoxy>acetate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 120h;100%
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetonitrile for 8h; Heating;95%
With potassium carbonate In N,N-dimethyl-formamide at 75 - 80℃; for 1.5h;90%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

1-(benzenesulfonyl)-3-methylimidazolium triflate
142841-88-1

1-(benzenesulfonyl)-3-methylimidazolium triflate

1,2-bis<(benzenesulfonyl)oxy>benzene
3905-43-9

1,2-bis<(benzenesulfonyl)oxy>benzene

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In tetrahydrofuran 1) 0 deg C, 30 min, 2) RT, 6 h;100%
(3-methyl-2-butenyl)trimethoxysilane
72142-16-6

(3-methyl-2-butenyl)trimethoxysilane

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

benzene-1,2-diol

triethylamine
121-44-8

triethylamine

triethylammonium bis(catecholato)(3-methyl-2-butenyl)siliconate
114571-77-6

triethylammonium bis(catecholato)(3-methyl-2-butenyl)siliconate

Conditions
ConditionsYield
at 45℃; for 5h;100%
allyltrimethoxysilane
2551-83-9

allyltrimethoxysilane

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

benzene-1,2-diol

triethylamine
121-44-8

triethylamine

triethylammonium bis(pyrocatecholato)allylsilicate
114612-18-9

triethylammonium bis(pyrocatecholato)allylsilicate

Conditions
ConditionsYield
for 5h; room temperature to 40 deg C;100%
at 40℃; for 4h; Inert atmosphere; Sealed tube;55%
(2-methyl-2-propenyl)trimethoxysilane
125715-25-5

(2-methyl-2-propenyl)trimethoxysilane

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

benzene-1,2-diol

triethylamine
121-44-8

triethylamine

triethylammonium bis(catecholato)(2-methyl-2-propenyl)siliconate
125715-30-2

triethylammonium bis(catecholato)(2-methyl-2-propenyl)siliconate

Conditions
ConditionsYield
at 45℃; for 5h;100%
2-Butenyltrimethoxysilane
13436-83-4

2-Butenyltrimethoxysilane

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

benzene-1,2-diol

triethylamine
121-44-8

triethylamine

triethylammonium bis(catecholato)-2-butenylsiliconate

triethylammonium bis(catecholato)-2-butenylsiliconate

Conditions
ConditionsYield
at 45℃; for 5h;100%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

1,1-dichloro-5-aza-2,8-dioxa-1-phosphaV-dibenzo<9,9',11,11'-tetra-tert-butyl>-bicyclo<3.3.0>octadiene
161868-74-2

1,1-dichloro-5-aza-2,8-dioxa-1-phosphaV-dibenzo<9,9',11,11'-tetra-tert-butyl>-bicyclo<3.3.0>octadiene

C34H44NO4P

C34H44NO4P

Conditions
ConditionsYield
In benzene for 24h; Ambient temperature;100%
3,4-Difluorobenzonitrile
64248-62-0

3,4-Difluorobenzonitrile

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

benzene-1,2-diol

2-cyanodibenzo[1,4]dioxine
234113-44-1

2-cyanodibenzo[1,4]dioxine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; toluene at 125 - 130℃;100%
With potassium carbonate In N,N-dimethyl-formamide; toluene at 130 - 135℃; Etherification; cyclization;98%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

C6-C4 carboxylic acids; C6-C4 aldehydes; C6-C4 ketones; mixture of

C6-C4 carboxylic acids; C6-C4 aldehydes; C6-C4 ketones; mixture of

Conditions
ConditionsYield
With ozone In water at 20℃; for 0.1h; pH=2; Oxidation; Formation of xenobiotics;100%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

triphenyl(1,2-phenylenedioxy)phosphorane
62785-50-6

triphenyl(1,2-phenylenedioxy)phosphorane

Conditions
ConditionsYield
at 70 - 80℃; for 2h;100%
(E)-(2-(phenyldiazenyl)phenyl)boronic acid
866252-03-1

(E)-(2-(phenyldiazenyl)phenyl)boronic acid

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

benzene-1,2-diol

2-[2-(phenylazo)phenyl]-1,3,2-benzodioxaborole

2-[2-(phenylazo)phenyl]-1,3,2-benzodioxaborole

Conditions
ConditionsYield
In toluene for 4h; Heating;100%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

tetraethylene glycol monoacrylate
19812-60-3

tetraethylene glycol monoacrylate

CH2CHC(O)(OCH2CH2)4OB(O2C6H4)

CH2CHC(O)(OCH2CH2)4OB(O2C6H4)

Conditions
ConditionsYield
Stage #1: benzene-1,2-diol With Trimethyl borate In acetonitrile at 60℃; for 1h;
Stage #2: tetraethylene glycol monoacrylate In acetonitrile for 2h; Further stages.;
100%
diethylzinc
557-20-0

diethylzinc

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

benzene-1,2-diol

A

ethane
74-84-0

ethane

B

zinc pyrocatecholate
10586-34-2

zinc pyrocatecholate

Conditions
ConditionsYield
react. of the educts in a molar ratio of 1:1;A 100%
B n/a
boric acid
11113-50-1

boric acid

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

benzene-1,2-diol

triphenylhydroxysilane
791-31-1

triphenylhydroxysilane

2-triphenylsiloxy-1,3,2-benzodioxaborole
82172-55-2

2-triphenylsiloxy-1,3,2-benzodioxaborole

Conditions
ConditionsYield
In benzene byproducts: H2O; azeotropic removal of water; elem. anal.;100%
Trimethyl borate
121-43-7

Trimethyl borate

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

benzene-1,2-diol

tetraethylene glycol monoacrylate
19812-60-3

tetraethylene glycol monoacrylate

CH2CHC(O)(OCH2CH2)4OB(O2C6H4)

CH2CHC(O)(OCH2CH2)4OB(O2C6H4)

Conditions
ConditionsYield
In acetonitrile stirring of catechol and B(OMe)3 at 60 °C for 1h, addn of tetraethylene glycol monoacrylate, 2 h stirring; cooling, vac. evapn. at 40 °C for 24 h;100%
(E)-dihydroxy(2-{[4-(trifluoromethyl)phenyl]azo}phenyl)borane
1048382-97-3

(E)-dihydroxy(2-{[4-(trifluoromethyl)phenyl]azo}phenyl)borane

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

benzene-1,2-diol

(E)-2-(2-{[4-(trifluoromethyl)phenyl]azo}phenyl)-1,3,2-benzodioxaborole

(E)-2-(2-{[4-(trifluoromethyl)phenyl]azo}phenyl)-1,3,2-benzodioxaborole

Conditions
ConditionsYield
In toluene for 16h; Heating;100%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

N-(trimethoxysilylmethyl)hexahydroazepin-2-one
76128-65-9

N-(trimethoxysilylmethyl)hexahydroazepin-2-one

dicyclohexylammonium bis(1,2-catecholato-O,O')-[(2-oxohexahydroazepin-1-yl)methyl-C,O]silicate

dicyclohexylammonium bis(1,2-catecholato-O,O')-[(2-oxohexahydroazepin-1-yl)methyl-C,O]silicate

Conditions
ConditionsYield
In o-xylene at 130 - 140℃;100%
triethylene glucol monomethyl ether
112-35-6

triethylene glucol monomethyl ether

lithium tetramethanolatoborate
6867-35-2

lithium tetramethanolatoborate

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

benzene-1,2-diol

C20H34BO10(1-)*Li(1+)

C20H34BO10(1-)*Li(1+)

Conditions
ConditionsYield
Stage #1: triethylene glucol monomethyl ether; lithium tetramethanolatoborate for 24h; Reflux; Inert atmosphere;
Stage #2: benzene-1,2-diol for 24h; Reflux; Inert atmosphere;
100%
9,9-didodecylfluorene-2,7-diboronic acid
480424-86-0

9,9-didodecylfluorene-2,7-diboronic acid

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

benzene-1,2-diol

C49H64B2O4
1446012-94-7

C49H64B2O4

Conditions
ConditionsYield
In toluene Reflux; Inert atmosphere;100%
boric acid
11113-50-1

boric acid

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

benzene-1,2-diol

tris(catecholato)diboron
37737-62-5

tris(catecholato)diboron

Conditions
ConditionsYield
In toluene Dean-Stark; Reflux;100%
2,2'-dihydroxy-1,1'-binaphthyl-3,3'-diboronic acid

2,2'-dihydroxy-1,1'-binaphthyl-3,3'-diboronic acid

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

benzene-1,2-diol

C32H20B2O6

C32H20B2O6

Conditions
ConditionsYield
With sodium sulfate In toluene at 50℃; Reflux;100%
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

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

benzene-1,2-diol

o-(1-methoxyethoxy)-phenol
51487-87-7

o-(1-methoxyethoxy)-phenol

Conditions
ConditionsYield
With trifluoroacetic acid In dimethylsulfoxide-d6 at 20℃; for 1h;100%
Triisopropyl borate
5419-55-6

Triisopropyl borate

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

benzene-1,2-diol

C23H22BNO3

C23H22BNO3

Conditions
ConditionsYield
In toluene at 80℃; for 1h; Inert atmosphere;100%
Stage #1: Triisopropyl borate; benzene-1,2-diol In toluene Inert atmosphere; Reflux;
Stage #2: (S)-diphenylprolinol In toluene at 80℃; for 1h; Inert atmosphere; Reflux;
100%

120-80-9Related news

Highly sensitive and stable laccase based amperometric biosensor developed on nano-composite matrix for detecting Pyrocatechol (cas 120-80-9) in environmental samples09/03/2019

The present study aims at fabricating a laccase based amperometric biosensor for detection of pyrocatechol in environmental samples. Trametes versicolor laccase was co-immobilized in a nanocomposite matrix comprising of osmium tetroxide on poly 4-vinylpyridine, multiwalled carbon nanotubes, Nafi...detailed

Pyrocatechol (cas 120-80-9) as a surface capping molecule on rutile TiO2 (110)09/02/2019

A ‘cap and dip’ method of adsorbing ruthenium di-2,2′-bipyridyl-4,4′-dicarboxylic acid diisocyanate (N3 dye) on a rutile TiO2 (110) surface was investigated using pyrocatechol as a capping molecule. This method involves cleaning the rutile surface in ultra-high vacuum (UHV), depositing pyroc...detailed

Boron removal using chelating resins with Pyrocatechol (cas 120-80-9) functional groups08/31/2019

Owing to broad applications of boron products in many industries, boron waste pollutes the groundwater and leads to a chain of environment and health problems. In this research, a new kind of chelating resins with pyrocatechol functional group was developed, which could be used in various condit...detailed

Kinetics of deposition and stability of Pyrocatechol (cas 120-80-9) –FeIII coordinated films08/30/2019

Metal coordination between polyphenols and metal cations like Fe3 + allows to produce conformal homogeneous and robust coatings on a vast variety of materials. The deposition kinetics and the stability of the obtained films are however only poorly investigated. In the present article it is shown...detailed

Electrodeposition of Pyrocatechol (cas 120-80-9) based films: Influence of potential scan rate, Pyrocatechol (cas 120-80-9) concentration and pH08/28/2019

Films based on catechols constitute a novel class of surface functionalization methods. Those films are produced by a complexation mechanism with metal cations. The deposition of films is accompagnied with the formation of colloids in solution. As an alternative, herein an electrochemical method...detailed

120-80-9Relevant articles and documents

Titanium Substitution in Silicon-free Molecular Sieves: Anatase-free TAPO4-5 and TAPO4-11 Synthesis and Characterisation for Hydroxylation of Phenol

Ulagappan, N.,Krishnasamy, V.

, p. 373 - 374 (1995)

Titanium-substituted ALPO4-5 and ALPO4-11 are synthesised using a modified procedure; they catalyse the hydroxylation of phenol to the extent of ca. 32percent, with good selectivity to catechol.

New hydrotalcite-like anionic clays containing Zr4+ in the layers

Velu,Ramaswamy, Veda,Ramani,Chanda, Bhanu M.,Sivasanker

, p. 2107 - 2108 (1997)

New hydrotalcite-like anionic clays containing Zr4+ in the brucite-like layers are synthesised by a simple coprecipitation technique; these materials show very interesting properties as catalysts for liquid-phase hydroxylation of phenol with H2O2.

An iron-based micropore-enriched silica catalyst:: In situ confining of Fe2O3 in the mesopores and its improved catalytic properties

Long, Saifu,Zhou, Shijian,Yang, Fu,Lu, Kangchao,Xi, Tao,Kong, Yan

, p. 76064 - 76074 (2016)

Surface exposed catalytic active species are thought to be responsible for overall catalytic activity and selectivity. In this paper, controllable contents of iron oxides were in situ introduced into the inner surface of anionic surfactant-templated mesop

Heterogeneous Nitrogen-doped Graphene Catalysed HOO? Generation via a Non-radical Mechanism for Base-free Dakin Reaction

Sun, Wei,Gao, Lingfeng,Sun, Xu,Yang, Hua,Zheng, Gengxiu

, p. 5210 - 5216 (2019)

A heterogeneous nitrogen-doped graphene catalytic pathway for H2O2 activation to generate alkaline hydrogen peroxide (HOO?) through a non-radical mechanism was reported. Remarkably, the heterogeneous catalytic procedure has been used for the evergreen and environmentally Dakin reaction without using any transition metals, homogeneous bases, ligands, additives or promoters, completely. The study of catalyst structure and catalytic activities indicate that the most active sites are created by the graphitic N atoms at zig-zag edges of the sheets. In addition, N as dopant element changes the reactivity of the neighbour C atoms, and leads to the formation of carbon-hydroperoxide (C?(HOOH)) and C?O* (C?O?) transition state species on the graphene surface in catalytic the reaction. (Figure presented.).

Application of advanced oxidation processes for removing salicylic acid from synthetic wastewaters

Chen, Xue Ming,da Silva, Djalma Ribeiro,Martínez-Huitle, Carlos A.

, p. 101 - 104 (2010)

In this study, advanced oxidation processes (AOPs) such as anodic oxidation (AO), UV/H2O2 and Fenton processes (FP) were investigated for the degradation of salicylic acid (SA) in lab-scale experiments. Boron-doped diamond (BDD) film electrodes using Ta as substrates were employed for AO of SA. In the case of FP and UV/H2O2, most favorable experimental conditions were determined for each process and these were used for comparing with AO process. The study showed that the FP was the most effective process under acidic conditions, leading to the highest rate of SA degradation in a very short time interval. However, the results showed that Ta/BDD films had high electrocatalytic activity for complete degradation of SA; even if it employs more time for complete elimination of the SA respect to FP. Additionally, AO led to a sixfold acceleration of the oxidation rate compared with the UV/H2O2 process. Finally a rough comparison of the specific energy consumption shows that AO process reduced the energy consumption by at least 90% compared with the UV/H2O2 process.

Mechanistic investigations in ultrasound-assisted biodegradation of phenanthrene

Kashyap, Niharika,Roy, Kuldeep,Moholkar, Vijayanand S.

, (2020)

This study has addressed the biodegradation of polycyclic aromatic hydrocarbon, phenanthrene using Candida tropicalis. Optimization using central composite statistical design yielded optimum experimental parameters as: pH = 6.2, temperature = 33.4 °C, mechanical shaking = 190 rpm and % inoculum = 9.26% v/v. Sonication of biodegradation mixture at 33 kHz and 10% duty cycle in log phase (12 h per day for 4 days) resulted in a 25% enhancement in phenanthrene removal. Profiles of specific growth rate (μ) and specific degradation rate (q) versus initial substrate concentration were fitted to Haldane substrate inhibition model. Both μ and q showed maxima for initial concentration of 100 mg L?1. Kinetic analysis of degradation profiles showed higher biomass yield coefficient and smaller decay coefficient in presence of sonication. Expression of total intracellular proteins in control and test experiments were analyzed using SDS–PAGE. This analysis revealed overexpression of enzyme catechol 2,3-dioxygenase (in meta route metabolism) during sonication which is involved in ring cleavage of phenanthrene. Evaluation of cell viability after sonication by flow cytometry analysis revealed > 80% live cells. These effects are attributed to enhanced cellular transport induced by intense microturbulence generated by sonication.

-

Popoff,Theander

, p. 1576 (1970)

-

-

Mc Kagne

, p. 2447 (1971)

-

Biocatalytic Methyl Ether Cleavage: Characterization of the Corrinoid-Dependent Methyl Transfer System from Desulfitobacterium hafniense

Richter, Nina,Farnberger, Judith E.,Pompei, Simona,Grimm, Christopher,Skibar, Wolfgang,Zepeck, Ferdinand,Kroutil, Wolfgang

, p. 2688 - 2695 (2019)

The ether functionality represents a very common motif in organic chemistry and especially the methyl ether is commonly found in natural products. Its formation and cleavage can be achieved via countless chemical procedures. Nevertheless, since in particular the cleavage often involves harsh reaction conditions, milder alternatives are highly demanded. Very recently, we have reported on a biocatalytic shuttle catalysis concept for reversible cleavage and formation of phenolic O-methyl ethers employing a corrinoid-dependent methyl transferase system from the anaerobic organism Desulfitobacterium hafniense. Here we report the technical study of this system, focusing on the demethylation of guaiacol as model reaction. The optimal buffer-, pH-, temperature- and cofactor-preferences were determined as well as the influence of organic co-solvents. Beside methyl cobalamin also hydroxocobalamin turned out to be a suitable cofactor species, although the latter required activation. Various O-methyl phenyl ethers were successfully demethylated with conversions up to 82% at 10 mM substrate concentration. (Figure presented.).

Sodium Percarbonate: A Convenient Reagent for the Dakin Reaction

Kabalka, G. W.,Reddy, N. K.,Narayana, C.

, p. 865 - 866 (1992)

Sodium percarbonate, a readily available, inexpensive and easy to handle reagent efficiently oxidizes hydroxylated benzaldehydes and hydroxylated acetophenones to hydroxyphenols.

Binuclear furanyl-azine metal complexes encapsulated in NaY zeolite as efficiently heterogeneous catalysts for phenol hydroxylation

Ku?niarska-Biernacka,Raposo,Batista,Soares,Pereira,Parpot,Oliveira,Skiba,Jartych,Fonseca,Neves

, (2020)

Two different methods A and B were used for preparing binuclear furanyl-azine metal complexes encapsulated in NaY zeolite. These new heterogeneous catalysts based on Fe(II) or Cu(II) complexes with a metal/ligand molar ratio of 2:1, were characterized by different spectroscopic techniques and chemical analysis which confirm the presence of the metal complexes inside the supercages of the zeolite. M?ssbauer spectroscopy technique analysis confirms the presence of the Fe3+- complexes in octahedral coordination. The new heterogeneous catalysts were catalytic evaluated by phenol hydroxylation and compared with the encapsulated metal furanyl-azine complexes in NaY zeolite. The zeolite themselves do not present any activity and the presence of the metal complexes improve their activity. All heterogeneous catalysts enhance higher conversion of phenol to catechol.

Biodegradation of phenol by Chlamydomonas reinhardtii

Ghanotakis, Demetrios F.,Mavroudakis, Leonidas,Nazos, Theocharis T.,Pergantis, Spiros A.

, p. 383 - 395 (2020)

The data presented in this particular study demonstrate that the biodegradation of phenol by Chlamydomonas reinhardtii is a dynamic bioenergetic process mainly affected by the production of catechol and the presence of a growth-promoting substrate in the culture medium. The study focused on the regulation of the bioenergetic equilibrium resulting from production of catechol after phenol oxidation. Catechol was identified by HPLC-UV and HPLC-ESI-MS/MS. Growth measurements revealed that phenol is a growth-limiting substrate for microalgal cultures. The Chlamydomonas cells proceed to phenol biodegradation because they require carbon reserves for maintenance of homeostasis. In the presence of acetic acid (a growth-promoting carbon source), the amount of catechol detected in the culture medium was negligible; apparently, acetic acid provides microalgae with sufficient energy reserves to further biodegrade catechol. It has been shown that when microalgae do not have sufficient energy reserves, a significant amount of catechol is released into the culture medium. Chlamydomonas reinhardtii acts as a versatile bioenergetic machine by regulating its metabolism under each particular set of growth conditions, in order to achieve an optimal balance between growth, homeostasis maintenance and biodegradation of phenol. The novel findings of this study reveal a paradigm showing how microalgal metabolic versatility can be used in the bioremediation of the environment and in potential large-scale applications.

Structural and electrochemical properties of lutetium bis-octachloro-phthalocyaninate nanostructured films. Application as voltammetric sensors

Alessio,Apetrei,Rubira,Constantino,Medina-Plaza,De Saja,Rodrguez-Mndez

, p. 6754 - 6763 (2014)

Thin films of the bis[2,3,9,10,16,17,23,24-octachlorophthalocyaninate] lutetium(III) complex (LuPc2Cl32) have been prepared by the Langmuir-Blodgett and the Langmuir-Schaefer (LS) techniques. The influence of the chlorine substituents in the structure of the films and in their spectroscopic, electrochemical and sensing properties has been evaluated. The -A isotherms exhibit a monolayer stability greater than the observed in the unsubstituted analogue (LuPc2), being easily transferred to solid substrates, also in contrast to LuPc2. The LB and LS films present a linear growth forming stratified layers, monitored by UV-VIS absorption spectroscopy. The latter also revealed the presence of L LuPc2Cl32in the form of monomers and aggregates in both films. The FTIR data showed that the L LuPc2Cl32molecules present a non-preferential arrangement in both films. Monolayers of LB and LS were deposited onto 6 nm Ag island films to record surface-enhanced resonance Raman scattering (SERRS), leading to enhancement factors close to 2×103Finally, LB and LS films deposited onto ITO glass have been successfully used as voltammetric sensors for the detection of catechol. The improved electroactivity of the LB and LS films has been confirmed by the reduction of the overpotential of the oxidation of catechol. The enhancement of the electrocatalytic effect observed in LB and LS films is the result of the nanostructured arrangement of the surface which increases the number of active sites. The sensors show a limit of detection in the range of 10?5 mol/L.

Polymer supported nickel complex: Synthesis, structure and catalytic application

Sutar, Alekha Kumar,Maharana, Tungabidya,Das, Yasobanta,Rath, Prasanta

, p. 1695 - 1705 (2014)

In the present investigation, a new synthetic route for a novel recyclable free [3-MOBdMBn-Ni] and polystyrene-anchored [P-3-MOBdMBn-Ni] nickel complexes is presented. The free and polymer-anchored metal complexes were synthesized by the reaction of nickel (II) with one molar equivalent of unsupported N N'-bis (2-Hydroxy-3-methoxybenzaldehyde) 4-Methylbenzene-1,2-diamine (3-MOBdMBn) or polymer-supported (P-3-MOBdMBn) Schiff-base ligand in methanol under nitrogen atmosphere. The advantages of these polymer-supported catalysts are the low cost of catalyst and recyclability up to six times, due to easy availability of materials and simple synthetic route. The higher efficiency of complexation of nickel on the polymer-anchored 3-MOBdMBn Schiff base than the unsupported analogue is another advantage of this catalyst system. The structural study reveals that nickel(II) complex of 3-MOBdMBn is square planar in geometry. The catalytic activity of nickel complex towards the oxidation of phenol was investigated in the presence of hydrogen peroxide. Experimental results indicate that the reactivity of P-3-MOBdMBn-Ni was dramatically affected by the polymer support compared to free 3-MOBdMBn-Ni. The rates of oxidation (Rp) for unsupported and supported catalysts are 1.37 × 10-6 mole dm-3 s-1 and 2.33 × 10-6 mole dm-3 s-1 respectively. [Figure not available: see fulltext.]

-

Howe,Rao

, p. 2436 (1968)

-

ACYLATED FLAVANOLS AND PROCYANIDINS FROM SALIX SIEBOLDIANA

Hsu, Feng-Lin,Nonaka, Gen-Ichiro,Nishioka, Itsuo

, p. 2089 - 2092 (1985)

An homologous series of acylated flavan-3-ols and procyanidins have been isolated, together with the known procyanidins B-1, B-3 and trimer, from the bark of Salix sieboldiana.Chemical and spectroscopic evidence led to the assignments of their structures as the 3-O-(1,6-dihydroxy-2-cyclohexene-1-carboxylic acid ester) of (+)-catechin and the 1-hydroxy-6-oxo-2-cyclohexene carboxylic acid esters of (+)-catechin and procyanidins B-1, B-3 and trimer.Key Word Index - Salix sieboldiana; Salicaceae; bark; acylated flavan-3-ols; acylated procyanidins; 1-hydroxy-6-oxo-2-cyclohexene-1-carboxylic acid; 1,6-dihydroxy-2-cyclohexene-1-carboxylic acid .

Effects of tetrahydropterines on the generation of quinones catalyzed by tyrosinase

Garcia-Molina, Francis,Munoz-Munoz, Joseph Louis,Martinez-Ortiz, Francis,Tudela, Joseph,Garcia-Canovas, Francis,Rodriguez-Lopez, Joseph Neptune

, p. 1108 - 1109 (2010)

Tetrahydrobiopterine (6BH4) can diminish the oxidative stress undergone by keratinocytes and melanocytes by reducing the o-quinones generated by the oxidation of the corresponding o-diphenols. We found that 6BH4 and their analogs reduced all the o-quinones studied. The formal potentials of different quinone/diphenol pairs indicate that the o-quinones with withdrawing groups are more potent oxidants than those with donating groups.

Transition metal coordination polymers: Synthesis and catalytic study for hydroxylation of phenol and benzene

Abbo, Hanna S.,Titinchi, Salam J.J.

, p. 148 - 155 (2012)

New coordination polymers of Ni(II) and Cu(II) of the polymeric salen-type Schiff base ligand derived from the condensation of 5,5′-methylene bis-(salicyaldehyde) with 1,2-diaminopropane yielded N,N′-1,2- propylenebis(5-methylenesalicylidenamine) abbrevia

Single-Crystal-to-Single-Crystal [2 + 2] Photodimerization Involving B←N Coordination with Generation of a Thiophene Host

Campillo-Alvarado, Gonzalo,Li, Changan,Feng, Zhiting,Hutchins, Kristin M.,Swenson, Dale C.,H?pfl, Herbert,Morales-Rojas, Hugo,Macgillivray, Leonard R.

, p. 2197 - 2201 (2020)

We report on B←N coordination to support a single-crystal-to-single-crystal reaction in the solid state. A [2 + 2] photodimerization is achieved with face-to-face π-stacks of monotopic B←N adducts composed of a phenylboronic acid catechol ester and an alkene with a terminal thiophene group. The photoreaction generates a ditopic B-adduct involving a head-to-tail cyclobutane regio- and stereoselectively. The photodimerization is accompanied by an increase in the tetrahedral character of the B atom. The resulting boron enables channel confinement of chloroform upon recrystallization.

Copper(II)-Catalyzed Reactions of Activated Aromatics

Puzari,Baruah, Jubaraj B.

, p. 2344 - 2349 (2000)

The catalytic reaction of cis-bisglycinato copper(II) monohydrate in the presence of hydrogen peroxide leads to hydroxylation of phenol to give catechol and hydroquinone (1:1.2 ratio) in good yield. 2,6-Dimethylphenol can be hydroxylated by hydrogen peroxide and a catalytic amount of cis-bisglycinato copper(II) monohydrate to give an aggregate of 1,4-dihydroxy-2,6-dimethylbenzene and 2,6-dimethylphenol. A similar reaction of o-cresol gives 2,5-dihydroxytoluene. The reactivity of cis-bisglycinato copper(II) monohydrate in hydrogen peroxide with o-cresol is 4.5 times faster than that of a similar reaction by trans-bisglycinato copper(II) monohydrate. A catalytic reaction of cis-bisglycinato copper(II) monohydrate with aniline in aqueous hydrogen peroxide gives polyanilines in the form of pernigraniline with different amounts of Cu(OH)2 attached to them. The two major components of polyanilines obtained have Mn values of 1040 and 1500, respectively. Resistance of films of these polyanilines increases with temperatures from 40°C to a maximum value at 103°C and then decreases in the region of 103-150°C, showing the property of a thermoelectric switch. The aggregate prepared from hydroxylation of 2,6-dimethylphenol shows a similar property in the region of 30-180°C.

Imidazolium-Based Ionic Liquids as Efficient Reagents for the C?O Bond Cleavage of Lignin

Thierry, Marina,Majira, Amel,Pégot, Bruce,Cezard, Laurent,Bourdreux, Flavien,Clément, Gilles,Perreau, Fran?ois,Boutet-Mercey, Stéphanie,Diter, Patrick,Vo-Thanh, Giang,Lapierre, Catherine,Ducrot, Paul-Henri,Magnier, Emmanuel,Baumberger, Stéphanie,Cottyn, Betty

, p. 439 - 448 (2018)

The demethylation of lignin in ionic liquids (ILs) was investigated by using pure lignin model monomers and dimers together with dioxane-isolated lignins from poplar, miscanthus, and maize. Different methylimidazolium ILs were compared and the samples were treated with two different heating processes: microwave irradiation and conventional heating in a sealed tube. The conversion yield and influence of the treatment on the lignin structure were assessed by 31P NMR spectroscopy, size-exclusion chromatography, and thioacidolysis. The acidic methylimidazolium IL [HMIM]Br was shown to be an effective combination of solvent and reagent for the demethylation and depolymerization of lignin. The relatively mild reaction conditions, the clean work-up, and the ability to reuse the IL makes the described procedure an attractive and new green method for the conversion of lignin to produce phenol-rich lignin oligomers.

Selective oxidation of phenol and benzoic acid in water via home-prepared TiO2 photocatalysts: Distribution of hydroxylation products

Bellardita, Marianna,Augugliaro, Vincenzo,Loddo, Vittorio,Megna, Bartolomeo,Palmisano, Giovanni,Palmisano, Leonardo,Puma, Maria Angela

, p. 79 - 89 (2012)

The hydroxylation of phenol (a substrate containing an electron donor group) and of benzoic acid (a substrate containing an electron withdrawing group) has been carried out by the photocatalytic method in aqueous suspensions containing commercial or home prepared TiO2 samples. The aim of the work was to study the distribution of hydroxylation products when different photocatalysts were used and to correlate the selectivity to some physico-chemical features of the powders. The samples were characterized by X-ray diffraction, thermogravimetry, determination of crystalline phase percentage, specific surface area and zero charge point. The photoreactivity results indicate that the products of the primary oxidation of phenol are the ortho- and para-mono-hydroxy derivatives while those of benzoic acid are all the mono-hydroxy derivatives independently of the catalyst. The selectivity toward mono-hydroxy derivatives shows a strong dependence on catalyst hydroxylation and crystallinity degrees: the highest selectivity values were obtained by using the commercial samples that resulted the least hydroxylated and the most crystalline ones. A kinetic model, taking into account the mineralization and the partial oxidation reaction routes, is proposed by using the Langmuir-Hinshelwood model.

-

Kiprianow,Ssytsch

, (1933)

-

Role of catechol in the radical reduction of B-alkylcatecholboranes in presence of methanol

Povie, Guillaume,Villa, Giorgio,Ford, Leigh,Pozzi, Davide,Schiesser, Carl H.,Renaud, Philippe

, p. 803 - 805 (2010)

Mechanistic investigations on the previously reported reduction of B-alkylcatecholboranes in the presence of methanol led to the disclosure of a new mechanism involving catechol as a reducing agent. More than just revising the mechanism of this reaction, we disclose here the surprising role of catechol, a chain breaking antioxidant, which becomes a source of hydrogen atoms in an efficient radical chain process.

Determination of catalytic oxidation products of phenol by RP-HPLC

Qiao, Jun-Qin,Yuan, Na,Tang, Chang-Jin,Yang, Jing,Zhou, Jian,Lian, Hong-Zhen,Dong, Lin

, p. 549 - 558 (2012)

A reversed-phase high-performance liquid chromatography (RP-HPLC) with ultraviolet detection was established for the determination of phenol, catechol, hydroquinone, and p-benzoquinone in the reaction solution of catalytic oxidation of phenol using hydrogen peroxide as the oxidant and copper-doped FeSBA-15 zeolite as the catalyst. Separation was accomplished on a reversed-phase C18 column, and the elution condition was optimized by changing the composition of the mobile phase. A good resolution of all of the relative components in the reaction solution was achieved when the mobile phase was methanol-water-1% acetic acid aqueous solution = 10:50:40 (v/v/v). The concentrations of phenol, catechol, hydroquinone, and p-benzoquinone were determined in 11 different reaction solutions by the external standard method. The proposed HPLC method was simple, accurate, reliable, and suitable for tracing the amount of target products during the catalytic oxidation reaction of phenol. The results can provide data support for evaluating the properties of catalysts, and, thus, guide the selection of catalysts for the industrial production of dihydric phenol. Springer Science+Business Media B.V. 2011.

Multi-Enzymatic Cascade Reactions for the Synthesis of cis,cis-Muconic Acid

Di Nardo, Giovanna,Gazzola, Silvia,Gilardi, Gianfranco,Pollegioni, Loredano,Rosini, Elena,Valetti, Francesca,Vignali, Elisa

, p. 114 - 123 (2021/10/07)

Lignin valorization allows the generation of a number of value-added products such as cis,cis-muconic acid (ccMA), which is widely used for the synthesis of chemicals for the production of biodegradable plastic materials. In the present work, we reported the first multi-enzymatic, one-pot bioconversion process of vanillin into ccMA. In details, we used four sequential reactions catalyzed by xanthine oxidase, O-demethylase LigM (and the tetrahydrofolate-regeneration enzyme methyl transferase MetE), decarboxylase AroY (based on the use of E. coli transformed cells) and catechol 1,2-dioxygenase CatA. The optimized lab-scale procedure allowed to reach, for the first time, the conversion of 5 mM vanillin into ccMA in ~30 h with a 90% yield: this achievement represents an improvement in terms of yields and time when compared to the use of a whole-cell system. This multi-enzymatic system represents a sustainable alternative for the production of a high value added product from a renewable resource. (Figure presented.).

The role of remote flavin adenine dinucleotide pieces in the oxidative decarboxylation catalyzed by salicylate hydroxylase

Brand?o, Tiago A. S.,Nagem, Ronaldo A. P.,Pereira, Mozart S.,Richard, John P.,de Araújo, Simara S.

, (2021/12/30)

Salicylate hydroxylase (NahG) has a single redox site in which FAD is reduced by NADH, the O2 is activated by the reduced flavin, and salicylate undergoes an oxidative decarboxylation by a C(4a)-hydroperoxyflavin intermediate to give catechol. We report experimental results that show the contribution of individual pieces of the FAD cofactor to the observed enzymatic activity for turnover of the whole cofactor. A comparison of the kinetic parameters and products for the NahG-catalyzed reactions of FMN and riboflavin cofactor fragments reveal that the adenosine monophosphate (AMP) and ribitol phosphate pieces of FAD act to anchor the flavin to the enzyme and to direct the partitioning of the C(4a)-hydroperoxyflavin reaction intermediate towards hydroxylation of salicylate. The addition of AMP or ribitol phosphate pieces to solutions of the truncated flavins results in a partial restoration of the enzymatic activity lost upon truncation of FAD, and the pieces direct the reaction of the C(4a)-hydroperoxyflavin intermediate towards hydroxylation of salicylate.

One-pot production of phenazine from lignin-derived catechol

He, Zhimin,Qi, Wei,Ren, Tianyu,Yan, Ning

supporting information, p. 1224 - 1230 (2022/02/17)

Upgrading lignin-derived monomeric products is crucial in bio-refineries to effectively utilize lignin. Herein, we report a simple strategy to convert catechol to phenazine, a useful N-heterocycle three-aromatic-ring compound, whose current synthetic procedure is complex via a petroleum-derived feedstock. The reaction uses catechol as the sole carbon source and aqueous ammonia as reaction media and a nitrogen source. Without additional solvents, phenazine was obtained in 67% yield in the form of high purity crystals (>97%) over a Pd/C catalyst after a one-pot-two-stage reaction. When cyclohexane was used as a co-solvent in the first step, a higher yield (81%) and purity (>99%) were achieved. Mechanistic investigations involving control experiments and an isotope labeling study reveal that hydrogenation, amination, coupling and dehydrogenation reactions are the key steps leading to phenazine formation. The conversion of other lignin-derived catechols highlights that the protocol is extendable to produce substituted phenazines.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 120-80-9