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123-30-8

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123-30-8 Usage

description

4-Aminophenol (or para-aminophenol or p-aminophenol) is the organic compound with the formula H2NC6H4OH, belongs to the class of organic compounds known as aniline and substituted anilines.Typically available as a white powder, it was commonly used as a developer for black-and-white film, marketed under the name Rodinal.Reflecting its slightly hydrophilic character, the white powder is moderately soluble in alcohols and can be recrystallized from hot water. In the presence of a base, it oxidizes readily. The methylated derivatives N-methylaminophenol and N,N-dimethylaminophenol are of commercial value.The compound is one of three isomeric aminophenols, the other two being 2-aminophenol and 3-aminophenol.

Chemical Properties

Different sources of media describe the Chemical Properties of 123-30-8 differently. You can refer to the following data:
1. 4-Aminophenol is a white or light yellow-brown crystals. It is slightly soluble in water and ethanol but insoluble in benzene and chloroform. It will quickly exhibit brown color after being dissolved in alkaline solution.
2. o-Aminophenol appears as colorless needles or as white crystalline substance turning tan to brown on exposure to air. slightly soluble in water and ethanol, insoluble in benzene and chloroform, and quickly turns brown when dissolved in lye.

Uses

Different sources of media describe the Uses of 123-30-8 differently. You can refer to the following data:
1. 4-Aminophenol is widely used in the synthesis of pharmaceuticals, dyes and other organic products and is mainly for the synthesis of paracetamol, clofibrate ketone, vitamin B1 and compound nicotinamide. It can be used for the production of Sulphur Blue FBG and weak acid dyes such as yellow 5G.The product is the intermediate of pharmaceutical intermediates, dyes and other fine chemicals. It can be used for the production of paracetamol, azo dyes, sulfur dyes, acid dyes, fur dye and developer, antioxidants as well as oil additive.It can be used for gold assay as well as determination of copper, iron, magnesium, vanadium, nitrite and cyanate, antioxidants.p-Aminophenol is an oxidative hair dye precursor. It is incorporated in oxidative hair dye formulations and in the bottle on the market at a maximum concentration of 1.8% and is typically mixed in a 1:1 ratio with an oxidative agent thereby reaching a concentration of 0.9% for in use application.
2. 4-Aminophenol is suitable for use in the synthesis of 2,2-bis(4-aminophenoxy) benzonitrile [4-APBN], a monomer required for the preparation of series of polyamides and poly(amide-imide)s. It may be used as derivatization reagent to improve the ionization of aliphatic and aromatic aldehydes by paper spray ionization mass spectrometry.

Preparation

Different sources of media describe the Preparation of 123-30-8 differently. You can refer to the following data:
1. 5 g of phenylhydroxylamine are slowly added to 100 ml of 50% sulphuric acid, cooled in a freezing mixture, 500 ml of water poured in, and the whole boiled until a sample, tested with chromic acid solution, gives a smell of quinone and no smell of nitrobenzene. The liquid is neutralised with sodium bicarbonate, saturated with common salt, and extracted with ether. The ether is removed by evaporation, and the residue washed with cold water and dissolved in hot water. The solution is filtered hot, and cooled, and the 4-aminophenol again extracted with ether. Yield almost theoretical. Colourless crystals; somewhat soluble in water; m.p. 185° C.Systematic organic chemistry, by W. M. Cumming, 209, 1937.
2. Conventionally 4-aminophenol was manufactured using iron-acid reduction of p-nitrobenzene. Reduction using iron-acid is a multi-step process. The modern method is the catalytic dehydrogenation of nitrobenzene to 4-aminophenol using a noble metal catalyst in the presence of an acidic medium. This method also produces aniline as a side-product. The advantage of a reduction using a noble metal catalyst is that it involves a single step reaction, an environment friendly and more efficient process, as there is no evolution of an environmentally harmful gas. Moreover, the side-product aniline is also a valuable chemical.synthesis of 4-aminophenol

Toxicity and protection

It is toxic. The p-amino phenol has double toxicity of both aniline and phenol. Absorption of it through the skin can cause dermatitis as well as cause methemoglobinemia and asthma. The contact of its hydrochloride with the skin can cause severe itching or eczema. Subcutaneous injection-cats-half lethal dose-LD50: 37mg/kg.

Description

4-Aminophenol, also known as 4-hydroxyaniline, is an organic building block. Its quantification in water samples upto the detection limit of 8×10-10mol l-1 has been proposed by employing single-wall carbon nanotubes (SWNT)-nafion film coated glassy carbon electrodes. It is present as the main contaminant in pharmaceutical formulations of paracetamol. High-performance liquid chromatographic (HPLC) method with amperometric detection has been reported for its determination in various analgesic formulations. It has been reported to be formed from the reduction of 4-nitrophenol (Nip) under metal-free conditions catalyzed by N-doped graphene (NG).

Application

The main and the most significant use of 4-Aminophenol is for the manufacturing of Paracetamol, an analgesic and antipyretic drug. In addition to paracetamol, it is a key element in the synthesis of pharmaceutical ingredients and important industrial chemicals like Acebutolol, Ambroxol, Sorafenib and so on.p-aminophenol is widely used in preparation of fabric dyes and hair dyes, and is also used as a developing agent in photography for creating black and white images. It acts as a corrosion inhibitor in paints and as anti-corrosive lubricating agent in 2-cycle engines. It is also used as a wood stain, giving rose-like colour to timber. p-Aminophenol is one of key ingredients for synthesis of rubber antioxidants. Moreover, it is often used as a reagent for analysing metals like Copper, Magnesium, Vanadium and Gold, compounds like Nitrites and Cyanates, and antioxidants.

Definition

ChEBI: 4-aminophenol is an amino phenol (one of the three possible isomers) which has the single amino substituent located para to the phenolic -OH group. It has a role as a metabolite and an allergen.

Synthesis Reference(s)

Synthesis, p. 285, 1971Tetrahedron Letters, 34, p. 2441, 1993 DOI: 10.1016/S0040-4039(00)60436-7

General Description

P-aminophenol appears as white or reddish-yellow crystals or light brown powder. Turns violet when exposed to light. (NTP, 1992)

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Heat (decomposition forming HCN, nitrous vapors, CO); water (CO2); reacts violently with acids, bases, alcohols and amines causing fire and explosion hazards [Handling Chemicals Safely 1980 p. 647].

Health Hazard

p-Aminophenol is of moderately low toxicity but has caused dermal sensitization and kidney injury; the potential for producing methemoglobin is of relatively minor importance. The oral LD50 in rats was 671 mg/kg.1 Effects included central nervous system depression. A solution of 2.5% applied to abraded skin of rabbits was a mild irritant.1 p- Aminophenol caused dermal sensitization in guinea pigs, and skin sensitization has been reported in humans.2,3 The dermal LD50 in rabbits was greater than 8 g/kg, which strongly suggests that absorption through the skin is minimal.4 Single nonlethal acute doses in rats produced proximal renal tubular necrosis of the pars recta.

Fire Hazard

Flash point data are not available for 4-Aminophenol. 4-Aminophenol is probably combustible.

Flammability and Explosibility

Nonflammable

Contact allergens

This hair dye is frequently implicated in contact dermatitis in hairdressers, customers, or people sensitized to para-phenylenediamine, by the way of “blackhenna” temporary tattoos.

Safety Profile

Poison by ingestion, subcutaneous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. An allergen and skin and eye irritant. Mutation data reported. Can cause contact dermatitis, bronchial asthma, and methemoglobinemia with cyanosis. When heated to decomposition it emits toxic fumes of NOx,.

Potential Exposure

Workers may be exposed to oAminophenol during its use as a chemical intermediate; in the manufacture of azo and sulfur dyes; and in the photographic industry. There is potential for consumer exposure to o-Aminophenol because of its use in dyeing hair, fur, and leather. The compound is a constituent of 75 registered cosmetic products suggesting the potential for widespread consumer exposure. p-Aminophenol is used mainly as a dye, dye intermediate and as a photographic developer; and in small quantities in analgesic drug preparation. Consumer exposure to p-aminophenol may occur from use as a hairdye or as a component in cosmetic preparations. m-Aminophenol is used mainly as a dye intermediate.

Shipping

UN2512 Aminophenols (o-; m-; p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials

Purification Methods

Crystallise it from EtOH, then water, excluding oxygen. It sublimes at 110o/0.3mm. It has been purified by chromatography on alumina with a 1:4 (v/v) mixture of absolute EtOH/*benzene as eluent. [Beilstein 13 IV 1014.]

Incompatibilities

These phenol/cresol materials can react with oxidizers; reaction may be violent. Incompatible with strong reducing substances such as alkali metals, hydrides, nitrides, and sulfides. Flammable gas (H2) may be generated, and the heat of the reaction may cause the gas to ignite and explode. Heat may be generated by the acidbase reaction with bases; such heating may initiate polymerization of the organic compound. Reacts with boranes, alkalies, aliphatic amines, amides, nitric acid, sulfuric acid. Phenols are sulfonated very readily (e.g., by concentrated sulfuric acid at room temperature). These reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid and can explode when heated. Many phenols form metal salts that may be detonated by mild shock.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Check Digit Verification of cas no

The CAS Registry Mumber 123-30-8 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 3 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 123-30:
(5*1)+(4*2)+(3*3)+(2*3)+(1*0)=28
28 % 10 = 8
So 123-30-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2

123-30-8 Well-known Company Product Price

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  • Alfa Aesar

  • (A13581)  4-Aminophenol, 98%   

  • 123-30-8

  • 50g

  • 170.0CNY

  • Detail
  • Alfa Aesar

  • (A13581)  4-Aminophenol, 98%   

  • 123-30-8

  • 250g

  • 328.0CNY

  • Detail
  • Alfa Aesar

  • (A13581)  4-Aminophenol, 98%   

  • 123-30-8

  • 1000g

  • 579.0CNY

  • Detail
  • Alfa Aesar

  • (A13581)  4-Aminophenol, 98%   

  • 123-30-8

  • 5000g

  • 2308.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1148)  4-Aminophenol (Acetaminophen RCK)  pharmaceutical secondary standard; traceable to USP

  • 123-30-8

  • PHR1148-1G

  • 804.73CNY

  • Detail
  • Sigma-Aldrich

  • (35837)  4-Aminophenol  PESTANAL®, analytical standard

  • 123-30-8

  • 35837-1G

  • 194.22CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001563)  MesalazineimpurityA  European Pharmacopoeia (EP) Reference Standard

  • 123-30-8

  • Y0001563

  • 1,880.19CNY

  • Detail
  • USP

  • (1021204)  4-Aminophenol  United States Pharmacopeia (USP) Reference Standard

  • 123-30-8

  • 1021204-100MG

  • 4,662.45CNY

  • Detail

123-30-8SDS

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 4-aminophenol

1.2 Other means of identification

Product number -
Other names 4-NH2-Phenol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:123-30-8 SDS

123-30-8Synthetic route

4-nitro-phenol
100-02-7

4-nitro-phenol

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With copper(I) chloride; potassium borohydride In methanol for 0.166667h; Ambient temperature;100%
With palladium diacetate; carbon monoxide; triphenylphosphine In water; acetic acid at 56℃; under 532 Torr; for 14h;100%
With hydrazine hydrate In ethanol at 80℃;100%
aniline
62-53-3

aniline

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With dihydrogen peroxide In water at 20℃; for 1.66667h; Reagent/catalyst; UV-irradiation; Green chemistry; regioselective reaction;100%
With dihydrogen peroxide; polymer 1-A In methanol for 0.05h; Ambient temperature;4.9%
With dihydrogen peroxide; polymer 1-A In methanol for 0.05h; Product distribution; Kinetics; Ambient temperature; various catalysts were used;4.9%
4-acetaminophenol
103-90-2

4-acetaminophenol

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With ammonium bromide; ethylenediamine at 70℃; for 5h; Reagent/catalyst; Temperature; Microwave irradiation;100%
With ammonium bromide; ethylenediamine at 70℃; for 5h; Microwave irradiation; Inert atmosphere; neat (no solvent);99%
With ammonium iodide; hydrazine hydrate at 50℃; for 12h; Inert atmosphere; Sealed tube;97%
carbamate de methyle et de N(hydroxy-4 phenyle)
54840-09-4

carbamate de methyle et de N(hydroxy-4 phenyle)

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With 3-azapentane-1,5-diamine at 130℃; for 12h; Sealed tube;99%
4-azidophenol
24541-43-3

4-azidophenol

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 20℃; chemoselective reaction;98%
With aluminium(III) iodide In benzene for 0.166667h; Reduction; Heating;93%
With gallium(III) triflate; potassium iodide In acetonitrile at 60℃; for 1h; Inert atmosphere; Green chemistry; chemoselective reaction;93%
4-(trimethylsilyloxy)aniline
36309-42-9

4-(trimethylsilyloxy)aniline

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;98%
With nano magnetic sulfated zirconia (Fe3O4 at ZrO2/SO42-) In neat (no solvent) at 20℃; for 0.25h; Green chemistry;83%
With Kaolinitic clay; water for 0.0416667h; Irradiation; microwave;63%
4-N-tert-butoxycarbonylaminophenol
54840-15-2

4-N-tert-butoxycarbonylaminophenol

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With water at 100℃; for 2h; Inert atmosphere;97%
With water at 150℃; for 2h; Subcritical conditions;95%
HY-Zeolite In dichloromethane for 2h; Heating;92%
With 3-butyl-l-methyl-1H-imidazol-3-iumtrifloroacetate In 1,4-dioxane; water at 70 - 72℃; for 2h;82%
With H-β zeolite In dichloromethane for 10h; Heating;71%
4-bromo-phenol
106-41-2

4-bromo-phenol

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With ammonium hydroxide at 20℃; for 10h; Catalytic behavior;96%
With ammonia; triethylamine In water at 20℃; for 8h;95%
With ammonium hydroxide at 20℃; for 12h; Catalytic behavior;94%
4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With zinc In methanol at 25℃; for 0.166667h; Inert atmosphere;96%
With magnesium In methanol at 25℃; for 0.2h; Inert atmosphere;95%
With sodium dithionite; water In dimethyl sulfoxide at 20℃; pH=7.4; Kinetics; phosphate buffer;
With hydrogenchloride; tin(ll) chloride
With sodium hydroxide; zinc
4-Iodophenol
540-38-5

4-Iodophenol

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry;95%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 50℃; for 23h; Inert atmosphere;90%
With copper(I) oxide; ammonium hydroxide; potassium carbonate at 140℃; for 13h; Inert atmosphere;80%
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; liquid NH3;57%
(4-aminophenyl)boronic acid
89415-43-0

(4-aminophenyl)boronic acid

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With iron(III) oxide; oxygen In tetrahydrofuran Irradiation;95%
With iron(III) oxide; oxygen In tetrahydrofuran at 20℃; Irradiation;95%
With dihydrogen peroxide In water at 20℃; chemoselective reaction;95%
4-(2,4-Dimethyl-benzyloxy)-phenylamine
84253-23-6

4-(2,4-Dimethyl-benzyloxy)-phenylamine

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 3040 Torr; for 15h;94%
p-nitrosophenol
104-91-6

p-nitrosophenol

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With titanium(III) chloride In 1,4-dioxane at 20℃; for 4h; Product distribution; var. substituted nitrosobenzenes;93%
With nickel; methyl cyclohexane at 100 - 125℃; under 73550.8 - 110326 Torr; Hydrogenation;
With hydrogenchloride; tin
tert-butyldimethyl(4-nitrophenoxy)silane
117635-44-6

tert-butyldimethyl(4-nitrophenoxy)silane

A

4-amino-phenol
123-30-8

4-amino-phenol

B

4-[(tert-butyldimethylsilyl)oxy]aniline
111359-74-1

4-[(tert-butyldimethylsilyl)oxy]aniline

Conditions
ConditionsYield
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran; water at 20℃; for 0.5h;A 7%
B 92%
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;A 7%
B 92%
p-aminophenyl acetate
13871-68-6

p-aminophenyl acetate

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With amberlyst-15 In methanol at 20℃; for 3h;90%
4-(benzylamino)phenol
103-14-0

4-(benzylamino)phenol

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With ammonium formate; zinc In ethylene glycol for 0.05h; microwave irradiation;90%
With ammonium formate; magnesium In ethylene glycol for 0.05h; microwave irradiation;90%
4-[[tris(propan-2-yl)silyl]oxy]aniline
1016987-47-5

4-[[tris(propan-2-yl)silyl]oxy]aniline

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With potassium acetate In water; N,N-dimethyl-formamide at 70℃; for 22h;90%
benzyl 4-nitrophenyl ether
1145-76-2

benzyl 4-nitrophenyl ether

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h; Catalytic behavior; Reagent/catalyst;89%
With Pd(0)EnCat; ammonium formate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Irradiation; microwave;20%
benzyl 4-nitrophenyl carbonate
13795-24-9

benzyl 4-nitrophenyl carbonate

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.25h; chemoselective reaction;89%
benzyl 4-nitrophenyl ether
1145-76-2

benzyl 4-nitrophenyl ether

A

p-benzyloxyaniline
6373-46-2

p-benzyloxyaniline

B

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In various solvent(s) at 25℃; for 10h;A 88%
B 7%
ammonium acetate
631-61-8

ammonium acetate

hydroquinone
123-31-9

hydroquinone

A

4-acetaminophenol
103-90-2

4-acetaminophenol

B

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With acetic acid at 160 - 230℃; for 15h; Temperature; Autoclave; Inert atmosphere;A 88%
B n/a
4-(N-Benzyloxycarbonylamino)phenol
7107-59-7

4-(N-Benzyloxycarbonylamino)phenol

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With methylmagnesium bromide; hydrogen; palladium diacetate; nickel diacetate In water at 45℃; for 19h;88%
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.25h; chemoselective reaction;86%
(4-aminophenyl)boronic acid
89415-43-0

(4-aminophenyl)boronic acid

oxygen
80937-33-3

oxygen

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With triethanolamine In water at 20℃; for 18h; Sonication; Irradiation; Green chemistry;88%
3-(4-nitro-phenoxymethyl)-benzoic acid ethyl ester

3-(4-nitro-phenoxymethyl)-benzoic acid ethyl ester

A

ethyl 3-methylbenzoate
120-33-2

ethyl 3-methylbenzoate

B

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With magnesium In methanol at 20℃; for 5h;A n/a
B 87%
4-[(tert-butyldimethylsilyl)oxy]aniline
111359-74-1

4-[(tert-butyldimethylsilyl)oxy]aniline

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With lithium acetate In water; N,N-dimethyl-formamide at 70℃; for 24h; Inert atmosphere;87%
With sodium cyanide In ethanol; water at 80℃; for 38h; chemoselective reaction;27.3%
4-nitro-phenol
100-02-7

4-nitro-phenol

acetic anhydride
108-24-7

acetic anhydride

A

4-acetaminophenol
103-90-2

4-acetaminophenol

B

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With sodium tetrahydroborate; chloro-trimethyl-silane In methanol; water for 0.25h; Reagent/catalyst; Irradiation;A 86%
B 13%
nitrobenzene
98-95-3

nitrobenzene

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With palladium diacetate; carbon monoxide; triphenylphosphine In sulfuric acid; butan-1-ol at 56℃; under 532 Torr; for 30h;85%
With sulfuric acid; Pt/Al2O3; hydrogen; cetyltrimethylammonim bromide; zinc(II) sulfate In water at 120℃; under 7500.75 Torr; for 4h; Reagent/catalyst; Pressure;83%
With formic acid; sulfate-doped zirconia; cetyltrimethylammonim bromide at 150℃; for 6h; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube;51.3%
4-amino-phenol
123-30-8

4-amino-phenol

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-{[(4-chlorophenyl)methylidene]amino}phenol
1749-05-9

4-{[(4-chlorophenyl)methylidene]amino}phenol

Conditions
ConditionsYield
for 24h; Ambient temperature;100%
With piperidine In ethanol Condensation; Heating;85%
With dodecatungstosilic acid; phosphorus pentoxide In neat (no solvent, solid phase) at 20℃;82%
succinic acid anhydride
108-30-5

succinic acid anhydride

4-amino-phenol
123-30-8

4-amino-phenol

4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid
62558-67-2

4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid

Conditions
ConditionsYield
With sodium dodecyl-sulfate In methanol; water at 20℃; for 0.583333h;100%
With sodium dodecyl-sulfate In water87%
In water at 50℃;86%
trimethylsilyl isocyanate
1118-02-1

trimethylsilyl isocyanate

4-amino-phenol
123-30-8

4-amino-phenol

(4-Trimethylsilanyloxy-phenyl)-urea
100238-66-2

(4-Trimethylsilanyloxy-phenyl)-urea

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20 - 50℃; for 2h;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4-amino-phenol
123-30-8

4-amino-phenol

4-N-tert-butoxycarbonylaminophenol
54840-15-2

4-N-tert-butoxycarbonylaminophenol

Conditions
ConditionsYield
With triethylamine In methanol at 22℃; for 14h;100%
With guanidine hydrochloride In ethanol at 35 - 40℃; for 0.0166667h;100%
In tetrahydrofuran at 0℃; for 12h;100%
phenylene-1,2-diisothiocyanate
71105-17-4

phenylene-1,2-diisothiocyanate

4-amino-phenol
123-30-8

4-amino-phenol

1-(4-hydroxyanilino-thiocarbonyl)-benzimidazolidine-2-thione
75644-26-7

1-(4-hydroxyanilino-thiocarbonyl)-benzimidazolidine-2-thione

Conditions
ConditionsYield
for 1h; Solid phase reaction; cyclization; addition;100%
In acetonitrile for 0.5h; Ambient temperature;81%
2,6-dimethyl-4-oxo-5-phenyl-1,3-oxazinium perchlorate
63673-58-5

2,6-dimethyl-4-oxo-5-phenyl-1,3-oxazinium perchlorate

4-amino-phenol
123-30-8

4-amino-phenol

perchlorate 2,6-dimethyl-5-phenyl-1-(4'-hydroxyphenyl)-4-oxopyrimidinium
122664-34-0

perchlorate 2,6-dimethyl-5-phenyl-1-(4'-hydroxyphenyl)-4-oxopyrimidinium

Conditions
ConditionsYield
In acetic acid for 48h; Ambient temperature;100%
In acetic acid for 0.5h; Heating;94%
triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

4-amino-phenol
123-30-8

4-amino-phenol

4-[[tris(propan-2-yl)silyl]oxy]aniline
1016987-47-5

4-[[tris(propan-2-yl)silyl]oxy]aniline

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 26h; Inert atmosphere;100%
With 1H-imidazole for 26h; Inert atmosphere;85%
With 1H-imidazole In dichloromethane at 15℃; for 12h;73.9%
4-amino-phenol
123-30-8

4-amino-phenol

4-amino(2H4)phenol
70237-44-4

4-amino(2H4)phenol

Conditions
ConditionsYield
Stage #1: 4-amino-phenol With diclazuril; water-d2 at 175℃; for 0.333333h; microwave irradiation;
Stage #2: With water
100%
With hydrogen chloride In water-d2 at 28 - 180℃; for 42h; Inert atmosphere; Sealed tube; Microwave irradiation;50%
With hydrogenchloride; water-d2 In water-d2 at 180℃; for 7h; Microwave irradiation;
4-amino-phenol
123-30-8

4-amino-phenol

4-hydroxybenzenediazonium tetrafluoroborate

4-hydroxybenzenediazonium tetrafluoroborate

Conditions
ConditionsYield
With acetic acid; isopentyl nitrite In ethanol; water at -10℃; for 1.5h;100%
With sodium tetrafluoroborate; perchloric acid; sodium nitrite In water at -10℃; for 24h;
With tetrafluoroboric acid; isopentyl nitrite In ethanol at 0℃; for 1h;
4-amino-phenol
123-30-8

4-amino-phenol

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

4-(4-nitrophenoxy)aniline
6149-33-3

4-(4-nitrophenoxy)aniline

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 90℃;100%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 12h;71%
With potassium carbonate In dimethyl sulfoxide at 70℃;67%
4-amino-phenol
123-30-8

4-amino-phenol

7-benzyloxy-4-chloro-6-methoxyquinazoline
162364-72-9

7-benzyloxy-4-chloro-6-methoxyquinazoline

4-((7-(benzyloxy )-6-methoxyquinazolin-4-yl)oxy)aniline
516526-37-7

4-((7-(benzyloxy )-6-methoxyquinazolin-4-yl)oxy)aniline

Conditions
ConditionsYield
With sodium hydroxide; tetrabutyl-ammonium chloride In water; butanone for 2h; Heating / reflux;100%
With sodium hydroxide; tetrabutyl-ammonium chloride In water; butanone for 2h; Heating / reflux;100%
Stage #1: 4-amino-phenol With sodium hydride In dimethyl sulfoxide; mineral oil at 17 - 25℃; for 0.166667h; Inert atmosphere;
Stage #2: 7-benzyloxy-4-chloro-6-methoxyquinazoline In dimethyl sulfoxide; mineral oil at 22 - 90℃; for 1h; Inert atmosphere;
91%
4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine
871024-38-3

4-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

4-amino-phenol
123-30-8

4-amino-phenol

4-[(5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl)oxy]aniline
919278-08-3

4-[(5-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-yl)oxy]aniline

Conditions
ConditionsYield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 16h; Product distribution / selectivity;100%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 110℃; for 3h; Product distribution / selectivity;60%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 110℃; for 2h;60%
1-benzyloxymethyl-4-chloro-1H-pyrazolo[3,4-b]pyridine
924909-13-7

1-benzyloxymethyl-4-chloro-1H-pyrazolo[3,4-b]pyridine

4-amino-phenol
123-30-8

4-amino-phenol

4-(1-benzyloxymethyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline
924909-14-8

4-(1-benzyloxymethyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline

Conditions
ConditionsYield
Stage #1: 4-amino-phenol With potassium tert-butylate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 20℃; for 1h;
Stage #2: 1-benzyloxymethyl-4-chloro-1H-pyrazolo[3,4-b]pyridine In 1-methyl-pyrrolidin-2-one at 80℃; for 0.5h;
100%
4-amino-phenol
123-30-8

4-amino-phenol

3-(triethoxypropyl) isocyanate
24801-88-5

3-(triethoxypropyl) isocyanate

1-(3-(triethoxysilyl)propyl)-3-(4-hydroxyphenyl)urea
1028843-30-2

1-(3-(triethoxysilyl)propyl)-3-(4-hydroxyphenyl)urea

Conditions
ConditionsYield
In chloroform at 80℃; for 5h;100%
In chloroform at 80℃; for 5h;95%
1-chloro-4-(4-methoxyphenyl)phthalazine
128615-83-8

1-chloro-4-(4-methoxyphenyl)phthalazine

4-amino-phenol
123-30-8

4-amino-phenol

4-(4-(4-methoxyphenyl)phthalazin-1-ylamino)phenol hydrochloride
1071584-40-1

4-(4-(4-methoxyphenyl)phthalazin-1-ylamino)phenol hydrochloride

Conditions
ConditionsYield
In iso-butanol at 100℃;100%
In iso-butanol at 100℃;
4-amino-phenol
123-30-8

4-amino-phenol

2,4-Dihydroxybenzaldehyde
95-01-2

2,4-Dihydroxybenzaldehyde

4-((4-hydroxyphenylimino)methyl)benzene-1,3-diol
111279-02-8

4-((4-hydroxyphenylimino)methyl)benzene-1,3-diol

Conditions
ConditionsYield
With acetic acid In ethanol for 2h; Reflux; Inert atmosphere;100%
3,5-dihydroxybenzaldehyde
26153-38-8

3,5-dihydroxybenzaldehyde

4-amino-phenol
123-30-8

4-amino-phenol

(E)-5{(4-hydroxyphenylimino)methyl}benzene-1,3-diol

(E)-5{(4-hydroxyphenylimino)methyl}benzene-1,3-diol

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 3h;100%
In water at 25℃; for 2h;92%
In water at 20℃; for 2h;
4-amino-phenol
123-30-8

4-amino-phenol

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

C9H13N2O(1+)*Cl(1-)
2350-69-8

C9H13N2O(1+)*Cl(1-)

Conditions
ConditionsYield
With trichlorophosphate at 20℃; Cooling with ice;100%
3,5-dihydroxybenzaldehyde
26153-38-8

3,5-dihydroxybenzaldehyde

4-amino-phenol
123-30-8

4-amino-phenol

5-[(4-hydroxy-phenylimino)-methyl]-benzene-1,3-diol
1365617-17-9

5-[(4-hydroxy-phenylimino)-methyl]-benzene-1,3-diol

Conditions
ConditionsYield
With sodium sulfate In dichloromethane at 20℃; for 1h;100%
With sodium sulfate In dichloromethane at 20℃; for 3h; Solvent; Reagent/catalyst; Inert atmosphere;93%
4-amino-phenol
123-30-8

4-amino-phenol

N-Cyanoguanidine
127099-85-8, 780722-26-1

N-Cyanoguanidine

1-carbamimidamido-N-(4-hydroxyphenyl)methanimidamide hydrochloride
116604-04-7

1-carbamimidamido-N-(4-hydroxyphenyl)methanimidamide hydrochloride

Conditions
ConditionsYield
In acetonitrile at 150℃; for 4.5h; Inert atmosphere;100%
trimethylsilyl isocyanate
1118-02-1

trimethylsilyl isocyanate

4-amino-phenol
123-30-8

4-amino-phenol

1-(4-hydroxyphenyl)urea
1566-41-2

1-(4-hydroxyphenyl)urea

Conditions
ConditionsYield
In tetrahydrofuran at 65℃; for 6h;100%
bromo-4 chloro-3 pyridine
73583-41-2

bromo-4 chloro-3 pyridine

4-amino-phenol
123-30-8

4-amino-phenol

4-((3-chloropyridin-4-yl)oxy)aniline

4-((3-chloropyridin-4-yl)oxy)aniline

Conditions
ConditionsYield
Stage #1: 4-amino-phenol With potassium tert-butylate In N,N-dimethyl acetamide at 20℃; for 0.5h;
Stage #2: bromo-4 chloro-3 pyridine In N,N-dimethyl acetamide at 85℃; for 4h;
100%
2-((4-chlorobenzyl)oxy)-5-fluorobenzaldehyde

2-((4-chlorobenzyl)oxy)-5-fluorobenzaldehyde

4-amino-phenol
123-30-8

4-amino-phenol

4-((2-((4-chlorobenzyl)oxy)-5-fluorobenzyl)amino)phenol

4-((2-((4-chlorobenzyl)oxy)-5-fluorobenzyl)amino)phenol

Conditions
ConditionsYield
Stage #1: 2-((4-chlorobenzyl)oxy)-5-fluorobenzaldehyde; 4-amino-phenol With acetic acid In methanol at 20℃; Inert atmosphere;
Stage #2: With sodium cyanoborohydride In methanol Inert atmosphere;
99.8%
iminodicarboxylic acid di-tert-butyl ester
51779-32-9

iminodicarboxylic acid di-tert-butyl ester

4-amino-phenol
123-30-8

4-amino-phenol

4-N-tert-butoxycarbonylaminophenol
54840-15-2

4-N-tert-butoxycarbonylaminophenol

Conditions
ConditionsYield
In tetrahydrofuran for 12h; Inert atmosphere;99.46%
acetic anhydride
108-24-7

acetic anhydride

4-amino-phenol
123-30-8

4-amino-phenol

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With sodium dodecyl-sulfate In water99%
With silica gel for 0.5h; Time; Milling;99%
With sulfuric acid supported on poly(4-vinylpyridine) (P4VP) In dichloromethane at 20℃; for 1.25h;98%
acetic anhydride
108-24-7

acetic anhydride

4-amino-phenol
123-30-8

4-amino-phenol

4-acetoxyacetanilide
2623-33-8

4-acetoxyacetanilide

Conditions
ConditionsYield
With silver trifluoromethanesulfonate at 60℃; for 0.05h; neat (no solvent);99%
With 2,3-dihydro-5,7-bismethyl-1,4-diazepine monohydroperchlorate In neat (no solvent) at 40℃; for 1h;99%
With pyridine at 100℃;90%
4-amino-phenol
123-30-8

4-amino-phenol

Benzoyl isothiocyanate
532-55-8

Benzoyl isothiocyanate

N1-Benzoyl-N2-<4-hydroxyphenyl>thiourea
5461-34-7

N1-Benzoyl-N2-<4-hydroxyphenyl>thiourea

Conditions
ConditionsYield
In acetone for 0.5h; Heating;99%
In acetone at 20℃; for 1h; Sonication;91%
In acetone Ambient temperature;71%

123-30-8Relevant articles and documents

A New Class of 1-Aryl-5,6-dihydropyrrolo[2,1-a]isoquinoline Derivatives as Reversers of P-Glycoprotein-Mediated Multidrug Resistance in Tumor Cells

Nevskaya, Alisa A.,Matveeva, Maria D.,Borisova, Tatiana N.,Niso, Mauro,Colabufo, Nicola A.,Boccarelli, Angelina,Purgatorio, Rosa,de Candia, Modesto,Cellamare, Saverio,Voskressensky, Leonid G.,Altomare, Cosimo D.

, p. 1588 - 1596 (2018)

A number of aza-heterocyclic compounds, which share the 5,6-dihydropyrrolo[2,1-a]isoquinoline (DHPIQ) scaffold with members of the lamellarin alkaloid family, were synthesized and evaluated for their ability to reverse in vitro multidrug resistance in cancer cells through inhibition of P-glycoprotein (P-gp) and/or multidrug-resistance-associated protein 1. Most of the investigated DHPIQ compounds proved to be selective P-gp modulators, and the most potent modulator, 8,9-diethoxy-1-(3,4-diethoxyphenyl)-3-(furan-2-yl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carbaldehyde, attained sub-micromolar inhibitory potency (IC50: 0.19 μm). Schiff bases prepared by the condensation of some 1-aryl-DHPIQ aldehydes with p-aminophenol also proved to be of some interest, and one of them, 4-((1-(4-fluorophenyl)-5,6-dihydro-8,9-dimethoxypyrrolo[2,1-a]isoquinolin-2-yl)methyleneamino)phenol, had an IC50 value of 1.01 μm. In drug combination assays in multidrug-resistant cells, some DHPIQ compounds, at nontoxic concentrations, significantly increased the cytotoxicity of doxorubicin in a concentration-dependent manner. Studies of structure–activity relationships and investigation of the chemical stability of Schiff bases provided physicochemical information useful for molecular optimization of lamellarin-like cytotoxic drugs active toward chemoresistant tumors as well as nontoxic reversers of P-gp-mediated multidrug resistance in tumor cells.

Green synthesis of the Ag/HZSM-5 nanocomposite by using Euphorbia heterophylla leaf extract: A recoverable catalyst for reduction of organic dyes

Tajbakhsh, Mahmood,Alinezhad, Heshmatollah,Nasrollahzadeh, Mahmoud,Kamali, Taghi A.

, p. 258 - 265 (2016)

During this paper, the Ag/HZSM-5 nanocomposite has been successfully synthesized by using an aqueous extract of Euphorbia heterophylla leaves as a stabilizing and reducing agent. The green synthesized Ag/HZSM-5 nanocomposite was characterized by FT-IR (Fourier transform infrared spectroscopy), FESEM (field emission scanning electron microscopy), EDS (energy dispersion X-ray spectroscopy), UV-vis, XRD (X-ray powder diffraction) and elemental mapping. The Ag/HZSM-5 nanocomposite was found to be efficient nanocatalyst for the reduction of organic dyes such as Methylene blue (MB), Congo red (CR), Rhodamine B (RhB) and 4-nitrophenol (4-NP) in water at room temperature. The catalytic activities of the nanocatalyst in reactions were monitored by using UV-vis spectroscopy. Interestingly, the Ag/HZSM-5 catalyst can be easily recovered and reused several times without any significant loss of catalytic efficiency.

Monooxygenase-like activity of methemoglobin with sodium sulfite as an efficient reductant

Song, Yonghong,Yang, Chi-Ming,Kluger, Ronald

, p. 4365 - 4366 (1993)

-

Synthesis of a superparamagnetic ultrathin FeCO3 nanorods-enzyme bionanohybrid as a novel heterogeneous catalyst

Benavente, Rocio,Lopez-Tejedor, David,Palomo, Jose M.

, p. 6256 - 6259 (2018)

Herein we report a straightforward synthesis of an ultrathin protein-iron(ii) carbonate nanorods (FeCO3-NRs) heterogeneous bionanohybrid at room temperature and in aqueous media. The enzyme induced the in situ formation of well-dispersed FeCO3 NRs on a protein network. The addition of NaBH4 as a reducing agent allowed us to obtain nanorods (5 × 40 nm) with superparamagnetic properties. This bionanohybrid showed excellent catalytic results in reduction, oxidation and C-C bond reactions.

Green Route for the Preparation of p-Aminophenol from Nitrobenzene by Catalytic Hydrogenation in Pressurized CO2/H2O System

Zhang, Tingting,Jiang, Jingyang,Wang, Yanhua

, p. 2050 - 2054 (2015)

The preparation of p-aminophenol from nitrobenzene by one-pot catalytic hydrogenation and in situ acid-catalyzed Bamberger rearrangement was first realized in a pressurized CO2/H2O system. By employing Pt-Sn/Al2O3 as catalyst, nitrobenzene could be converted to p-aminophenol with selectivity as high as 85% when the reaction was carried out at 140°C under 5.5 MPa CO2 and 0.2 MPa H2. This new protocol is environmentally benign because it is fully rid of the use of mineral acid by the application of self-neutralizable carbonic acid.

Nickel nanoparticle/carbon catalysts derived from a novel aqueous-synthesized metal-organic framework for nitroarene reduction

Martín-Jimeno, F. Julian,Martínez-Alonso, Amelia,Paredes, Juan I.,Suárez-García, Fabián,Tascón, Juan M. D.

, (2021)

Carbon-supported, non-noble metal-based catalysts derived from metal-organic frameworks (MOFs) are attractive alternatives to noble metal-based systems, but typical syntheses of the starting MOFs are not desirable from an environmental and practical perspective (e.g., they rely on non-innocuous organic solvents and long reaction times). Here, we report the preparation of a Ni-based MOF in aqueous medium, at moderate temperature (95 °C) and in a short reaction time (2 g?1 depending on the carbonization temperature applied to the MOF, as well as high Ni contents (between ~36 and 57 wt%). Notwithstanding the latter, the metal was homogeneously distributed throughout the carbon matrix in the hybrid and was quite resistant to extensive agglomeration and sintering, even at temperatures as high as 1000 °C. With increasing carbonization temperature, the Ni component was seen to go through different crystal phases, i.e., Ni3C phase → Ni hexagonal close-packed phase → Ni face-centered cubic phase. The results of the catalytic tests suggested the former and latter phases to be the most active towards the reduction of 4-NP, with catalytic activity values as high as 0.039 mol4-NP molNi?1 min?1.

Magnetic rod-based metal-organic framework metal composite as multifunctional nanostirrer with adsorptive, peroxidase-like and catalytic properties

Meteku, Benjamin Edem,Huang, Jiankun,Zeng, Jingbin,Aslam, Sobia,Zhang, Yu,Zhang, Xue,Cui, Bingwen,Wen, Cong-ying,Yan, Zifeng

, p. 3245 - 3251 (2021)

Although magnetic stirring is frequently used to enhance the kinetics for adsorption, chemical and biochemical reactions, the introduction of stirrers inevitably leads to the adsorption of analytes and thus interferes with the efficiency of the chemical process or reaction. In this work, magnetic Fe3O4 nanorods with tunable length-to-diameter ratio were synthesized via a hydrothermal method and used as templates for the in-situ depositing of MIL-100(Fe) and gold nanoparticles. Such nanorod-based material can not only function as an adsorbent, nanozyme, and a heterogeneous catalyst for corresponding applications but also serve as a magnetic nanostirrer to enhance kinetics. As a proof-of-concept, the capture of bacteria pathogen, mimic-peroxidase-based colorimetric detection of hydrogen peroxide, and the catalytic reduction of selected organic pollutants were conducted using the as-synthesized Fe3O4@MIL-100(Fe)-Au nanostirrer with and without magnetic field. The results show that the rates of bacteria capture, mimetic enzyme reaction and catalysis were tremendously expedited. We believe this magnetic field-assisted approach holds great promise for future applications, because, not only does it eliminate the use of external magnetic stirrers and thereby decrease the risk of foreign pollution but also, is adaptable for nanoscale reaction systems where conventional stirring is not applicable due to size limitations.

-

Matsumura,Sone

, p. 1406 (1931)

-

Spectrophotometric determination of paracetamol with microwave assisted alkaline hydrolysis

Xu, Chunli,Li, Baoxin

, p. 1861 - 1864 (2004)

A novel and rapid spectrophotometric method for the determination of paracetamol is proposed in this paper. The proposed method is based on the microwave assisted alkaline hydrolysis of paracetamol to p-aminophenol that reacts with S2- in the presence of Fe3+ as oxidant to produce a methylene blue-like dye having an absorptivity maximum at 540nm. The experiment showed that paracetamol could be hydrolysed quantitatively to p-aminophenol in only 1.5min under radiation power 640W using a microwave in NaOH medium. The system obeys Beer's law in the range of 0-3.0×10 -4moll-1 paracetamol. The molar absorptivity and Sandell's sensitivity were found to be 3.2×103lmol-1cm -1 and 0.047μgcm-2, respectively. The relative standard deviation (n=11) was 1.7% for 8.0×10-5moll-1 paracetamol. The method has been applied successfully to analysis of paracetamol in pharmaceutical preparation.

Highly efficient Au/TiO2 catalyst for one-pot conversion of nitrobenzene to p-aminophenol in water media

Zou, Luyao,Cui, Yuanyuan,Dai, Weilin

, p. 257 - 262 (2014)

Au/TiO2 catalyst is firstly reported to be efficient in the hydrogenation of nitrobenzene to produce p-aminophenol with a high PAP selectivity of 81% and overall yield more than 63%. The catalyst is also quite stable and can be reused for at least 4 times with only slight decrease in activity.

Carbonization of Co-BDC MOF results in magnetic C@Co nanoparticles that catalyze the reduction of methyl orange and 4-nitrophenol in water

Ahsan, Md. Ariful,Fernandez-Delgado, Olivia,Deemer, Eva,Wang, Huiyao,El-Gendy, Ahmed A.,Curry, Michael L.,Noveron, Juan C.

, (2019)

Herein we report a simple, facile and green technique for the preparation of magnetic cobalt nanoparticles (NPs) embedded on porous carbon (C@Co) nanocatalyst using MOFs template and explored for the catalytic reduction of Methyl orange (MO) and 4-Nitroph

Ir/C and Brφnsted acid functionalized ionic liquids an efficient catalytic system for hydrogenation of nitrobenzene to: P -aminophenol

Wang, Hong,Jiang, Taotao,Ma, Lei,Wang, Hanbing,Xu, Xiaoliang,Lu, Chunshan,Li, Xiaonian

, p. 31663 - 31670 (2017)

In this study, we found that the phenylhydroxylamine intermediate could desorb more easily from an Ir surface than from a Pt surface, which is beneficial for inhibiting the over-hydrogenation of phenylhydroxylamine to aniline. On the other hand, the Brφnsted acid functionalized ionic liquids with sulfonic acid and bisulfate anions were acidic enough to catalyze the Bamberger rearrangement to form p-aminophenol from phenylhydroxylamine. On this basis, a new catalytic system constructed by Ir/C and Brφnsted acid functionalized ionic liquid was applied, for the first time, to the one-pot hydrogenation of nitrobenzene to p-aminophenol. Our results indicate that the PAP selectivity of Ir/C and [SO3H-bmim][HSO4] Brφnsted functionalized ionic liquid was far more than that of the traditional Pt/C and sulfuric acid catalyst system. Furthermore, the dually functionalized ionic liquid ([HSO3-b-N-Bu3][HSO4]) can be used simultaneously as an acid catalyst and also as a surfactant, due to its higher lipophilicity. Therefore, our new catalytic system has unique advantages in the hydrogenation of nitrobenzene to p-aminophenol.

Adsorption driven formate reforming into hydride and tandem hydrogenation of nitrophenol to amine over PdO: Xcatalysts

Zhu, Xiaohui,Liang, Shipan,Chen, Shuang,Liu, Xiangdong,Li, Renhong

, p. 8332 - 8338 (2020)

Due to their high toxicity and non-biodegradability, efficient reduction of nitroarenes to amines is of great practical importance, yet it still remains a significant challenge. Herein, we report PdO/PdO2 nanoparticles uniformly supported on titanate nanotubes (PdOx/TiNTs) for catalyzing the tandem dehydrogenation of sodium formate (SF) and hydrogenation of p-nitrophenol (PNP) to p-aminophenol (PAmP) under mild conditions. Notably, SF adsorption is mainly driven by the hydrogen bonding interactions between the H atom in SF and surface Pd sites, which factually makes the interface of PdOx/TiNT-SF an effective platform for C-H activation. Meanwhile, it is also found that the efficiency of the hydrogenation reaction depends on the reduction rate of the nitro group to nitroso group, and the O atoms adjacent to Pd are considered as the essential sites that facilitate this process. On the basis of the above two effects, the PdOx/TiNT catalyst shows unprecedented catalytic activity (turnover frequency, TOF, is 45.6 h-1) and good selectivity (~100%) during PNP reduction at room temperature. This work deepens our understanding on tandem catalytic (de)hydrogenation systems, and will benefit the design of heterogeneous catalysts for the production of industrially important chemicals.

Kinetic rotating droplet electrochemistry: A simple and versatile method for reaction progress kinetic analysis in microliter volumes

Challier, Lylian,Miranda-Castro, Rebeca,Marchal, Damien,Noel, Vincent,Mavre, Francois,Limoges, Benoiit

, p. 14215 - 14228 (2013)

Here, we demonstrate a new generic, affordable, simple, versatile, sensitive, and easy-to-implement electrochemical kinetic method for monitoring, in real time, the progress of a chemical or biological reaction in a microdrop of a few tens of microliters, with a kinetic time resolution of ca. 1 s. The methodology is based on a fast injection and mixing of a reactant solution (1-10 μL) in a reaction droplet (15-50 μL) rapidly rotated over the surface of a nonmoving working electrode and on the recording of the ensuing transient faradaic current associated with the transformation of one of the components. Rapid rotation of the droplet was ensured mechanically by a rotating rod brought in contact atop the droplet. This simple setup makes it possible to mix reactants efficiently and rotate the droplet at a high spin rate, hence generating a well-defined hydrodynamic steady-state convection layer at the underlying stationary electrode. The features afforded by this new kinetic method were investigated for three different reaction schemes: (i) the chemical oxidative deprotection of a boronic ester by H2O2, (ii) a biomolecular binding recognition between a small target and an aptamer, and (iii) the inhibition of the redox-mediated catalytic cycle of horseradish peroxidase (HRP) by its substrate H2O2. For the small target/aptamer binding reaction, the kinetic and thermodynamic parameters were recovered from rational analysis of the kinetic plots, whereas for the HRP catalytic/inhibition reaction, the experimental amperometric kinetic plots were reproduced from numerical simulations. From the best fits of simulations to the experimental data, the kinetics rate constants primarily associated with the inactivation/reactivation pathways of the enzyme were retrieved. The ability to perform kinetics in microliter-size samples makes this methodology particularly attractive for reactions involving low-abundance or expensive reagents.

Synthesis of glucose-mediated Ag-γ-Fe2O3 multifunctional nanocomposites in aqueous medium - a kinetic analysis of their catalytic activity for 4-nitrophenol reduction

Kaloti, Mandeep,Kumar, Anil,Navani, Naveen K.

, p. 4786 - 4799 (2015)

This paper reports the synthesis of γ-Fe2O3 supported Ag nanoparticles (NPs) in aqueous medium by following a green approach. The presence of Fe2O3 in the gamma phase and silver in the nanocomposite has been confirmed by Raman spectroscopy, EDAX and XPS analyses. The presence of Ag in the nanocomposite is also indicated by UV spectroscopy. In the process of in situ generation of glucose mediated Ag NPs on the γ-Fe2O3 matrix, the size of γ-Fe2O3 nanoclusters reduced from 11.6 ± 1.6 to 9 ± 1 nm as was estimated from HRTEM analysis. Glucose served as an effective stabilizer for both Ag and γ-Fe2O3 in the nanocomposite. At lower concentrations of Ag (0.15-1.2 μM) the reduction of 4-nitrophenol (4-Nip) follows pseudo-first-order kinetics and the second order rate constant for this process was found to be 5.28 × 103 dm3 mol-1 s-1. Whereas, at higher concentrations (3.2-28.9 μM), it follows zero-order kinetics and occurred with a rate constant of 1 × 10-2 mol dm-3 s-1. The amount of silver in the nanocomposite is found to influence the kinetics of the catalytic reduction in a complex scheme following the Langmuir-Hinshelwood mechanism. The recyclability of the as-synthesized nanocomposite up to 7 cycles and the catalytic effect even at a very low silver concentration (0.15 μM) associated with high surface area and superparamagnetism suggest it to be a cost effective and environmentally friendly potential catalytic system.

Magnetic Fe3O4/graphene oxide/copper-based nanocomposite as a reusable catalyst for the reduction of 4-nitrophenol

Zabihzadeh, Mehdi,Shirini, Farhad,Tajik, Hassan,Shokri, Zahra,Karami, Shiva

, p. 121 - 127 (2020)

In the present investigation, Fe3O4/Graphene oxide/Pr–NH2–CuII was reported as a novel magnetically recoverable nanocomposite and characterized using various analytical techniques such as FT-IR spectroscopy, field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray spectroscopy (EDX), vibrating sample magnetometry (VSM), X-ray diffraction (XRD), and inductively coupled plasma (ICP). The catalytic performance of the synthesized catalyst was evaluated in the reduction of 4-nitrophenol to 4-aminophenol by an excess amount of sodium borohydride as the source of hydrogen in aqueous solution. The reaction was monitored by UV-vis spectroscopy at ambient temperature. Magnetic nature of the catalyst led to its simple recovery by a permanent magnet and excellent recyclability without appreciable loss of the catalytic activity.

Gold-Catalyzed Dearomative Spirocyclization of N-Aryl Alkynamides for the Synthesis of Spirolactams

Vacala, Taylor L.,Carlson, Paul R.,Arreola-Hester, Asa,Williams, Chloé G.,Makhoul, Evana W.,Vadola, Paul A.

, p. 1493 - 1501 (2018)

A catalytic redox-neutral method for the synthesis of spirolactams proceeding through the dearomative spirocyclization of N-aryl alkynamides is reported. In contrast to stoichiometric activating agents employed for related transformations, we show that the use of 5 mol % of Au(PPh3)Cl and AgOTf in dichloroethane at 50-80 °C leads to selective spirocyclization, furnishing the products in yields of 35-87%. The substrate scope of the reaction is good, with both electron-donating and electron-withdrawing groups being tolerated around the arene ring, as well as substitution at the amide nitrogen. The identity of the para-alkoxy group on the arene ring is key to achieving selectivity for spirocyclization over alternative mechanistic pathways. While the presence of a para-methoxy group leads to trace amounts of the desired spirolactams, the para-tert-butoxy or para-hydroxy substrate analogues furnish the spirolactams in good yield with high selectivity.

Preparation of bimetallic metal-organic framework microflowers by spray method

Zhang, Liying,Li, Linlin,Bai, Xiaojue,Xia, Mingjian,Shao, Lei,Wang, Tieqiang,Zhang, Xuemin,Li, Yunong,Qi, Xuan,Fu, Yu

, p. 175 - 177 (2019)

The NiCo-MOF microflowers are fabricated by a rapid spray method, which are assembled by 2D NiCo-MOF nanosheets with uniform crystal morphology and homogeneous dispersion of Ni and Co. Because of their large exposed active sites and nanoscale thickness, the NiCo-MOF microflowers exhibit good catalytic performance for the reduction of 4-nitrophenol.

Transfer Hydrogenation of Nitroarenes Catalyzed by CoCu Anchored on Nitrogen-doped Porous Carbon

Liu, Xiaotong,Zhang, Longkang,Wang, Junmin,Shang, Ningzhao,Gao, Shutao,Wang, Chun,Gao, Yongjun

, (2020)

The non-precious metal catalysts with high catalytic activity is extremely desirable but still full of challenges. In this paper, CoCu bimetal immobilized on nitrogen-doped porous carbon (CoCu-N-C) was prepared by an effective ligand-stabilized pyrolysis strategy. CoCu-N-C exhibited excellent catalytic efficiency for the transfer hydrogenation of nitroarenes with ammonia borane as hydrogen source, which can be ascribed to the well dispersed metal nanoparticles, the synergetic interaction of CoCu bimetal and nitrogen-doped carbon. The durability and recyclability experiments of the recycled CoCu-N-C catalyst indicated that no obvious change in catalytic performance was observed after five consecutive cycles. To gain insight into the catalytic mechanism of CoCu-N-C for the hydrogenation reaction, density functional theory calculations was also conducted. This work provides an universal approach for constructing highly efficient non-precious metal heterogeneous catalysts and which may find diverse high performance applications.

Flavhemoglobin: A Semisyntheic Hydroxylase Acting in the Absence of Reductase

Kokubo, Toshio,Sassa, Shigeru,Kaiser, E. T.

, p. 606 - 607 (1987)

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Synthesis of p-aminophenol by catalytic hydrogenation of nitrobenzene

Rode,Vaidya,Chaudhari

, p. 465 - 470 (1999)

The present work describes the preparation of p-aminophenol via single-step catalytic hydrogenation of nitrobenzene in acid medium. A conventional method of synthesis of p-aminophenol is a two-step reaction involving iron-acid reduction of p-nitrophenol. This method causes serious effluent disposal problems due to the stoichiometric use of iron-acid, which leads to the formation of Fe-FeO sludge (?2 kg/kg of product) in the process, which cannot be recycled. The single-step hydrogenation of nitrobenzene was carried out using platinum catalyst, and the process conditions were optimized. Complete conversion of nitrobenzene was achieved with selectivity to p-aminophenol as high as 75% under the best set of conditions. Furthermore, the catalyst can be easily recovered and efficiently recycled giving the TON as high as 1.38 κ' 10.5 This paper presents studies on the effect of various process parameters such as temperature, hydrogen pressure, and substrate and acid concentration on the rate of reaction and selectivity to p-aminophenol.

Contrasting effect of isoflurane on drug metabolism: Decreased type I and increased type II substrate metabolism in guinea pig liver microsomes

Mustafizur Rahman,Fujii, Kohyu,Kawamoto, Masashi,Yuge, Osafumi

, p. 331 - 337 (1996)

Inhalation anaesthetics might affect perioperative drug elimination by altering drug distribution, hepatic blood flow or drug metabolism. The in vitro effects of isoflurane on aniline hydroxylation and aminopyrine N-demethylation were investigated with guinea pig liver microsomes to assess the role of isoflurane on oxidative drug metabolism through the hepatic mixed-function oxidase system, p-Aminophenol and formaldehyde were measured spectrophotometrically as metabolic products of aniline hydroxylation and aminopyrine N-demethylation, respectively, where the reaction mixture consisted of a microsomal suspension, NADPH, aminopyrine or aniline, with or without isoflurane. The rate of cytochrome P-450 reduction by NADPH affected in the presence of isoflurane was investigated by spectrometric measurement of the CO-cytochrome P-450 complex formation at various times. Due to the addition of isoflurane, the V(max) values for aniline hydroxylation evidently increased except in high isoflurane concentration (3.33 mM) and for aminopyrine N-demethylation the value was significantly low only in the presence of a high isoflurane concentration, whereas the K(m) values significantly decreased in aniline hydroxylation and increased in aminopyrine N-demethylation, and isoflurane also accelerated the rate of cytochrome P-450 reduction by NADPH. These results reflect the inhibition of aminopyrine N-demethylation and activation of aniline hydroxylation in the presence of isoflurane as a consequence of isoflurane-accelerated cytochrome P-450 reduction by NADPH and/or drug-enzyme binding properties, and may have implications on the metabolism of perioperatively administered drugs during isoflurane anaesthesia.

Designed Meso-macroporous Silica Framework Impregnated with Copper Oxide Nanoparticles for Enhanced Catalytic Performance

Kanwar, Rohini,Bhar, Rekha,Mehta, Surinder Kumar

, p. 2087 - 2095 (2018)

The template efficacy of solid lipid nanoparticles for generating porous silica materials with the amalgamation of Cu-functionalized cetylpyridinium chloride (CPC; as a co-emulsifier and as a metal source for generation of CuO oxide nanoparticles) has bee

Catalytically Active Bimetallic Nanoparticles Supported on Porous Carbon Capsules Derived from Metal-Organic Framework Composites

Yang, Hui,Bradley, Siobhan J.,Chan, Andrew,Waterhouse, Geoffrey I. N.,Nann, Thomas,Kruger, Paul E.,Telfer, Shane G.

, p. 11872 - 11881 (2016)

We report a new methodology for producing monometallic or bimetallic nanoparticles confined within hollow nitrogen-doped porous carbon capsules. The capsules are derived from metal-organic framework (MOF) crystals that are coated with a shell of a secondary material comprising either a metal-tannic acid coordination polymer or a resorcinol-formaldehyde polymer. Platinum nanoparticles are optionally sandwiched between the MOF core and the shell. Pyrolysis of the MOF-shell composites produces hollow capsules of porous nitrogen-doped carbon that bear either monometallic (Pt, Co, and Ni) or alloyed (PtCo and PtNi) metal nanoparticles. The Co and Ni components of the bimetallic nanoparticles are derived from the shell surrounding the MOF crystals. The hollow capsules prevent sintering and detachment of the nanoparticles, and their porous walls allow for efficient mass transport. Alloyed PtCo nanoparticles embedded in the capsule walls are highly active, selective, and recyclable catalysts for the hydrogenation of nitroarenes to anilines.

High amplification rates from the association of two enzymes confined within a nanometric layer immobilized on an electrode: Modeling and illustrating example

Limoges, Benoit,Marchal, Damien,Mavre, Francois,Saveant, Jean-Michel

, p. 6014 - 6015 (2006)

Electrochemical responses (e.g., chronoamperometric) obtained with an immobilized enzyme that produces an electroactive species may be used to quantitate the amount of enzyme or the concentration of its substrate. It is shown, on theoretical and experimental bases, that product-to-substrate coupling with a second enzyme co-immobilized with the first within one or within a small number of monolayers, allows high amplification rates (higher than 1000), avoids membrane transport limitations, and lends itself to precise kinetic analyses that provide guidelines for optimization of the analytical sensitivity. Very large amplification factors, as large as several thousands, can be reached experimentally, in agreement with appropriately derived theoretical predictions, thus opening the route to the rational design of high-performance substrate sensing or affinity assays applications. Copyright

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter

supporting information, p. 133 - 146 (2021/11/04)

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Surface Roughness Effects of Pd-loaded Magnetic Microspheres on Reduction Kinetics of Nitroaromatics

An, Seonghwi,Manivannan, Shanmugam,Viji, Mayavan,Shim, Min Suk,Hwang, Byeong Hee,Kim, Kyuwon

supporting information, p. 894 - 899 (2021/05/06)

Metal nanoparticles decoration on magnetically active semiconductor materials is a common strategy to improve the colloidal stability, catalyst harvesting, and reuse. In this study, a surfactant-free solvothermal method followed by a heat treatment to pre

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