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100-02-7

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100-02-7 Usage

Description

4-Nitrophenol (also called p-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of hydroxyl group on the benzene ring. 4-Nitrophenol shows two polymorphs in the crystalline state. The alpha form is colorless pillars, unstable at room temperature, and stable toward sunlight. The beta form is yellow pillars, stable at room temperature, and gradually turns red upon irradiation of sunlight. Usually 4-nitrophenol exists as a mixture of these two forms. Generally, 4-nitrophenol is used in manufacturing of drugs (e.g., acetaminophen), fungicides, methyl and ethyl parathion insecticides, and dyes, and to darken leather.

Chemical Properties

Yellow to tan crystals or powder (mixed α- and β-forms), The (metastable) α-form crystallizes from toluene above 63°C, and the yellow, prismatic β-form crystallizes from toluene below 63°C. 4-Nitrophenol is not steam volatile and is much more soluble in water (30 % at 100°C) than the ortho isomer.

Uses

4-Nitrophenol is used in dyestuff and pesticide synthesis, as a fungicide, bactericide, and wood preservative, as a chemical indicator, and as a substrate for experiments on cytochrome P450 2E1.

Preparation

4-Nitrophenol was synthesized from p-nitrochlorobenzene by hydrolysis and acidification. Add 2320-2370L of sodium hydroxide solution with a concentration of 137-140g/L to the hydrolysis pot, and then add 600kg of molten p-nitrochlorobenzene. Heat to 152℃, pressure in the pot is 0.4MPa, then stop heating, the hydrolysis reaction exotherm makes the temperature and pressure rise naturally to 165℃, about 0.6MPa. keep 3h and take sample to check the end point of the reaction, after the reaction is finished, the hydrolysate is cooled to 120℃. Add 600L water and 50L concentrated sulfuric acid to the crystallization pot, press into the above hydrolysis and cool to about 50℃, add concentrated sulfuric acid to make the Congo red test paper purple, continue to cool to 30℃, filter, centrifuge to shake off the water, get more than 90% of 4-nitrophenol about 500kg, 92% yield.

Application

4-Nitrophenol (4-NP) is used to manufacture pharmaceuticals, fungicides, insecticides, and dyes and to darken leather. Indicator in 0.1% alcohol solution. pH: 5.6 colorless, 7.6 yellow. It can be used to prepare 4-aminophenol (4-AP), a key intermediate for the manufacture of analgesic and antipyretic drugs.

Definition

ChEBI: 4-nitrophenol is a member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group. It has a role as a human xenobiotic metabolite and a mouse metabolite. It is a conjugate acid of a 4-nitrophenolate.

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 1607, 1986 DOI: 10.1016/S0040-4039(00)84326-9

General Description

4-nitrophenol appears as a white to light yellow crystalline solid. Contact may severely irritate skin and eyes. Poisonous by ingestion and moderately toxic by skin contact.

Air & Water Reactions

Soluble in hot water and more dense than water.

Reactivity Profile

4-Nitrophenol is a slightly yellow, crystalline material, moderately toxic. Mixtures with diethyl phosphite may explode when heated. Decomposes exothermally, emits toxic fumes of oxides of nitrogen [Lewis, 3rd ed., 1993, p. 941]. Decomposes violently at 279°C and will burn even in absence of air [USCG, 1999]. Solid mixtures of the nitrophenol and potassium hydroxide (1:1.5 mol) readily deflagrate [Bretherick, 5th Ed., 1995].

Hazard

Toxic by ingestion.

Health Hazard

Acute inhalation or ingestion of 4-nitrophenol in humans causes headaches, drowsiness, nausea, and cyanosis. Contact with the eyes causes irritation.A study examining the acute effects of 4-nitrophenol from inhalation exposure in rats reported an increase in methemoglobin and corneal opacity. Tests involving acute exposure of rats and mice have shown 4-nitrophenol to have high toxicity from oral and dermal exposure.

Flammability and Explosibility

Nonflammable

Safety Profile

4-Nitrophenol is used to manufacture drugs, fungicides, insecticides, and dyes and to darken leather. Acute (short-term) inhalation or ingestion of 4-nitrophenol in humans causes headaches, drowsiness, nausea, and cyanosis (blue color in lips, ears, and fingernails). Contact with eyes causes irritation in humans. No information is available on the chronic (long-term) effects of 4-nitrophenol in humans or animals from inhalation or oral exposure. No information is available on the reproductive, developmental, or carcinogenic effects of 4-nitrophenol in humans. EPA has not classified 4-nitrophenol for potential carcinogenicity.

Metabolic pathway

4-[U-14C]Nitrophenol is conjugated as its b-glucoside (ca 22% of applied 14C) and gentiobioside, glc- b(126)-glc-b-4-nitrophenol (ca 64%), while about 7% of the parent remains unchanged in cell suspension cultures of Datura stramonium (L.). Gal-b-4-nitrophenol is found to be a minor metabolite.

Purification Methods

Crystallise 4-nitrophenol from water (which may be acidified, e.g. with N H2SO4 or 0.5N HCl), EtOH, aqueous MeOH, CHCl3, *benzene or pet ether, then dry it in vacuo over P2O5 at 25o. It can be sublimed at 60o/10-4mm. The 4-nitrobenzoate had m 159o (from EtOH). [Beilstein 6 IV 1279.]

Toxicity evaluation

The major hazards has been encountered in the use and handling of 4-nitrophenolstem from its toxicologic properties. 4-Nitrophenol irritates the eyes, skin, and respiratory tract. It may also cause inflammation of those parts. It has a delayed interaction with blood and forms methemoglobin which is responsible for methemoglobinemia, potentially causing cyanosis, confusion, and unconsciousness. When ingested, it causes abdominal pain and vomiting. Prolonged contact with skin may cause allergic response.

Check Digit Verification of cas no

The CAS Registry Mumber 100-02-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 100-02:
(5*1)+(4*0)+(3*0)+(2*0)+(1*2)=7
7 % 10 = 7
So 100-02-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H/p-1

100-02-7 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Alfa Aesar

  • (A14376)  4-Nitrophenol, 99%   

  • 100-02-7

  • 250g

  • 221.0CNY

  • Detail
  • Alfa Aesar

  • (A14376)  4-Nitrophenol, 99%   

  • 100-02-7

  • 1000g

  • 410.0CNY

  • Detail
  • Alfa Aesar

  • (A14376)  4-Nitrophenol, 99%   

  • 100-02-7

  • 5000g

  • 1763.0CNY

  • Detail
  • Supelco

  • (40056)  4-Nitrophenolsolution  certified reference material, 5000 μg/mL in methanol

  • 100-02-7

  • 000000000000040056

  • 533.52CNY

  • Detail

100-02-7SDS

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-nitrophenol

1.2 Other means of identification

Product number -
Other names 4-Nitrophenol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. 4-Nitrophenol is used to manufacture drugs (e.g., acetaminophen), fungicides, methyl and ethyl parathion insecticides, and dyes and to darken leather.
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:100-02-7 SDS

100-02-7Synthetic route

1-allyloxy-4-nitrobenzene
1568-66-7

1-allyloxy-4-nitrobenzene

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃;100%
With chloro-trimethyl-silane; sodium cyanoborohydride In acetonitrile at 20℃; for 0.25h; ether cleavage;95%
With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 1h;94%
1-(methoxymethoxy)-4-nitrobenzene
880-03-5

1-(methoxymethoxy)-4-nitrobenzene

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1h;100%
With diphosphorus tetraiodide In dichloromethane at 0℃; for 0.75h;92%
With bismuth(III) chloride In water; acetonitrile at 50℃; for 3h;92%
With Montmorillonite K 10 In benzene at 50℃; for 72h;20%
trans-2-(p-nitrophenoxy)-6-carboxytetrahydropyran
133754-19-5

trans-2-(p-nitrophenoxy)-6-carboxytetrahydropyran

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With sodium hydroxide; potassium chloride at 50℃; Rate constant; Mechanism; var. pH; other acetals; other solvent; rate constant vs. pH;100%
4-nitrophenol acetate
830-03-5

4-nitrophenol acetate

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 8h;100%
With ammonium acetate In methanol at 20℃; for 2h;99%
With Vigna unguiculata powder In water; isopropyl alcohol at 30℃; for 72h;99%
4-nitrophenyl methylsulphonylmethanesulphonate
13165-89-4

4-nitrophenyl methylsulphonylmethanesulphonate

benzylamine
100-46-9

benzylamine

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

N-benzyl (methylsulfonyl)methanesulfonamide

N-benzyl (methylsulfonyl)methanesulfonamide

Conditions
ConditionsYield
With pH 13 In water at 25℃;A n/a
B 100%
With potassium hydroxide at 25℃; Rate constant; also with benzylamine buffers; var. conc.;
1-(1,1-dimethyl-allyloxy)-4-nitro-benzene

1-(1,1-dimethyl-allyloxy)-4-nitro-benzene

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 24h;100%
tert-Butyl 4-nitrophenyl carbonate
13303-10-1

tert-Butyl 4-nitrophenyl carbonate

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With erbium(III) triflate In ethanol for 25h; Microwave irradiation;100%
With methanol; carbon tetrabromide; triphenylphosphine for 12h; Reflux;92%
With zinc diacetate; water-d2; N-ethyl-N,N-diisopropylamine; tris(2-benzylaminoethyl)amine In dimethylsulfoxide-d6 at 21.84℃; Kinetics; Reagent/catalyst;
4-nitrophenylboronic acid
24067-17-2

4-nitrophenylboronic acid

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With water; oxygen; sodium sulfite at 50℃; for 1h; Green chemistry;100%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 30h; Irradiation; Green chemistry;99%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile for 48h; Irradiation;99%
4-nitro-aniline
100-01-6

4-nitro-aniline

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With water; sodium hydroxide at 150℃; for 0.1h; Autoclave;100%
Stage #1: 4-nitro-aniline With tetrafluoroboric acid In water at 20℃; for 0.0333333h;
Stage #2: With sodium nitrite In water at 0℃; for 0.5h;
Stage #3: With copper(I) oxide; copper(II) sulfate In water at 0 - 20℃; for 0.5h;
87%
Stage #1: 4-nitro-aniline With sulfuric acid In water
Stage #2: With sulfuric acid; sodium nitrite In water at 0 - 5℃; for 0.166667h; Heating;
60%
2-phenylethanol
60-12-8

2-phenylethanol

p-nitrophenyl sulfate
1080-04-2

p-nitrophenyl sulfate

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

2-phenylethyl sulfate

2-phenylethyl sulfate

Conditions
ConditionsYield
With arylsulfate sulfotransferase from Desulfitobacterium hafniense In acetone at 30℃; for 96h; pH=9; Kinetics; pH-value; Green chemistry; Enzymatic reaction; regioselective reaction;A n/a
B 100%
4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With β-D-glucose; copper(II) acetate monohydrate; potassium hydroxide In water; dimethyl sulfoxide at 20 - 120℃; for 24h;99%
With tetra(n-butyl)ammonium hydroxide; water at 100℃; for 4h;96%
Stage #1: 4-chlorobenzonitrile With sodium hydroxide In water at 170℃; under 3750.38 Torr; for 8h; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 80℃; for 1h; pH=1.5; Temperature; pH-value; Pressure; Reagent/catalyst;
96.7%
para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
Stage #1: para-nitrophenyl bromide With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole In 1,4-dioxane; water at 100℃; for 20h; Inert atmosphere;
Stage #2: With hydrogenchloride In 1,4-dioxane; water at 20℃; Inert atmosphere;
99%
With β-D-glucose; copper(II) acetate monohydrate; potassium hydroxide In water; dimethyl sulfoxide at 20 - 120℃; for 24h;99%
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;99%
1-[(2-methoxyethoxy)methoxy]-4-nitrobenzene
198829-77-5

1-[(2-methoxyethoxy)methoxy]-4-nitrobenzene

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1.5h;99%
With diphosphorus tetraiodide In dichloromethane 0 degC, 25 min and room temp., 5 min;92%
4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With 2-(methylsulfonyl)ethyl alcohol; sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;99%
With sodium hydroxide In dimethyl sulfoxide at 80℃; for 12h;90%
With methyl propargyl alcohol; potassium tert-butylate In dimethyl sulfoxide at 125℃; for 0.0333333h; microwave irradiation;78%
tert-butyldimethyl(4-nitrophenoxy)silane
117635-44-6

tert-butyldimethyl(4-nitrophenoxy)silane

Cs2CO3

Cs2CO3

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 20℃; for 0.5h;99%
para-nitrophenyl triflate
17763-80-3

para-nitrophenyl triflate

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With tetraethylammonium hydroxide In 1,4-dioxane at 20℃; for 1h;99%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With β-D-glucose; copper(II) acetate monohydrate; potassium hydroxide In water; dimethyl sulfoxide at 20 - 120℃; for 16h;99%
With copper(I) oxide; N-phenylpicolinamide; sodium hydroxide In water; dimethyl sulfoxide at 160℃; for 0.166667h; Microwave irradiation;98%
With basolite C300; potassium hydroxide In water; dimethyl sulfoxide at 125℃; for 12h;96%
2-(4-nitrophenoxy)tetrahydropyran
20443-91-8

2-(4-nitrophenoxy)tetrahydropyran

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With montmorillonite K-10 In methanol at 40 - 50℃; for 0.4h;98%
With methanol; zirconium(IV) chloride at 20℃; for 5h;86%
With acid-washed bentonite In acetone at 40 - 50℃; for 0.333333h;86.7%
para-methoxynitrobenzene
100-17-4

para-methoxynitrobenzene

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With lithium chloride In N,N-dimethyl-formamide for 24h; Heating;98%
With water; hydrogen bromide; Aliquat 336 at 105℃; for 3.5h; Catalytic behavior;97%
With copper(I) oxide; sodium methylate In methanol at 185℃; for 12h; Autoclave;87%
tert-butyldimethyl(4-nitrophenoxy)silane
117635-44-6

tert-butyldimethyl(4-nitrophenoxy)silane

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With water; potassium carbonate In ethanol at 75℃; for 2h;98%
With triethylamine N-oxide In methanol for 0.5h;96%
With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 10h;96%
4-nitrophenyl 4-methylbenzenesulfonate
1153-45-3

4-nitrophenyl 4-methylbenzenesulfonate

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With cerium(III) chloride; sodium iodide In acetonitrile for 4h; tosylate cleavage; Heating;98%
With tetraethylammonium hydroxide In 1,4-dioxane at 20℃; for 24h;92%
With potassium fluoride on basic alumina for 0.1h; Substitution; microwave irradiation;86%
C22H15NO5
1093198-55-0

C22H15NO5

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In ethanol; benzene at 20℃; for 0.5h;98%
p-nitrophenyl sulfate
1080-04-2

p-nitrophenyl sulfate

Leu-enkephalin
58822-25-6

Leu-enkephalin

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

sulfated [Leu5]-enkephalin
80632-52-6

sulfated [Leu5]-enkephalin

Conditions
ConditionsYield
With arylsulfate sulfotransferase from Desulfitobacterium hafniense In aq. buffer at 30℃; for 144h; pH=8; Green chemistry; Enzymatic reaction; regioselective reaction;A n/a
B 98%
4-nitrophenylboronic acid
24067-17-2

4-nitrophenylboronic acid

oxygen
80937-33-3

oxygen

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With methylene blue; N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 7h; Schlenk technique; Irradiation;98%
4-(4'-Nitrophenoxy)-2,3,5,6-tetrafluoropyridine
83235-15-8

4-(4'-Nitrophenoxy)-2,3,5,6-tetrafluoropyridine

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether; Methyl thioglycolate In water; acetonitrile at 50℃; for 2h;98%
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene
171364-83-3

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With [Rh2(bpy)2(μ-OAc)2(OAc)2]; oxygen; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide under 760.051 Torr; for 18h; Irradiation;98%
With dihydrogen peroxide In ethanol at 20℃; for 0.5h; pH=9.2;
p-nitrophenyl methanesulfonate
20455-07-6

p-nitrophenyl methanesulfonate

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With tetraethylammonium hydroxide In 1,4-dioxane at 20℃; for 3h;97%
With sodium azide; copper(ll) sulfate pentahydrate; water; sodium carbonate; sodium L-ascorbate; L-proline In dimethyl sulfoxide at 70℃; for 24h;71%
4<(2-methyl-2-propenyl)oxy>-1-nitrobenzene
86497-88-3

4<(2-methyl-2-propenyl)oxy>-1-nitrobenzene

4-nitro-phenol
100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 24h;97%
(E)-N-butyl-3-(4-nitrophenoxy)-N-(2-(6-(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazin-3-yl)pyridin-3-yl)acrylamide

(E)-N-butyl-3-(4-nitrophenoxy)-N-(2-(6-(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazin-3-yl)pyridin-3-yl)acrylamide

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

6-butyl-3-(pyridin-2-yl)pyridazino[4,3-c][1,5]naphthyridin-5(6H)-one

6-butyl-3-(pyridin-2-yl)pyridazino[4,3-c][1,5]naphthyridin-5(6H)-one

Conditions
ConditionsYield
With Dess-Martin periodane In chloroform-d1 for 0.333333h;A 87%
B 97%
(E)-O-p-nitrophenyl-2,4-dinitrobenzaldoxime

(E)-O-p-nitrophenyl-2,4-dinitrobenzaldoxime

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

2,4-dinitrobenzonitrile
4110-33-2

2,4-dinitrobenzonitrile

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 25℃; for 7h; Kinetics; Reagent/catalyst;A n/a
B 96%
With triethylamine hydrochloride; triethylamine In water; acetonitrile at 25℃; Rate constant; different Et3N concentrations and compositions of solvent mixtures;
With sodium ethanolate In ethanol at 25℃; Kinetics; Further Variations:; Reagents; Elimination;
isocyanate de chlorosulfonyle
1189-71-5

isocyanate de chlorosulfonyle

4-nitro-phenol
100-02-7

4-nitro-phenol

N-<<(4-nitrophenyl)oxy>carbonyl>sulfamyl chloride
89692-65-9

N-<<(4-nitrophenyl)oxy>carbonyl>sulfamyl chloride

Conditions
ConditionsYield
In diethyl ether for 2h;100%
With benzene
In benzene
In dichloromethane at 20℃; for 1.5h;
With benzene
4-nitro-phenol
100-02-7

4-nitro-phenol

2-bromo-4-nitrophenol
5847-59-6

2-bromo-4-nitrophenol

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 8.5h; Heating;100%
With N-benzyl-N,N-dimethyl anilinium peroxodisulfate; potassium bromide In acetonitrile for 8h; Reflux; regioselective reaction;97%
With N-Bromosuccinimide; fluorosulphonic acid In acetonitrile at 20℃; for 48h;95%
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%
4-nitro-phenol
100-02-7

4-nitro-phenol

acetic anhydride
108-24-7

acetic anhydride

4-nitrophenol acetate
830-03-5

4-nitrophenol acetate

Conditions
ConditionsYield
K5 In acetonitrile at 20℃; for 0.333333h;100%
With SBA-15-Ph-Pr-SO3H at 20℃; for 0.833333h;100%
With magnesium(II) perchlorate at 20℃; for 1.5h;99%
4-nitro-phenol
100-02-7

4-nitro-phenol

benzoyl chloride
98-88-4

benzoyl chloride

p-nitrophenylbenzoate
959-22-8

p-nitrophenylbenzoate

Conditions
ConditionsYield
With pyridine at 0 - 20℃; Inert atmosphere;100%
With 4-(dimethylamino)pyridine hydrochloride In toluene at 110℃; for 6h;98%
With sodium hydride In tetrahydrofuran at 20℃; for 1h;97%
4-nitro-phenol
100-02-7

4-nitro-phenol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

p-nitrophenyl methanesulfonate
20455-07-6

p-nitrophenyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 0.75h;100%
With triethylamine In dichloromethane at 0 - 20℃;98%
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry;97%
4-nitro-phenol
100-02-7

4-nitro-phenol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-nitrophenyl 4-methylbenzenesulfonate
1153-45-3

4-nitrophenyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
Stage #1: 4-nitro-phenol; p-toluenesulfonyl chloride With potassium carbonate In acetone at 20 - 25℃; for 2.5h;
Stage #2: With hydrogenchloride In water; acetone
100%
With triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;99%
With potassium carbonate for 0.0833333h; microwave irradiation;98%
4-nitro-phenol
100-02-7

4-nitro-phenol

tetradecanoyl chloride
112-64-1

tetradecanoyl chloride

p-nitrophenyl myristate
14617-85-7

p-nitrophenyl myristate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 1h; Ambient temperature;100%
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
In 1,4-dioxane; pyridine for 2h; Ambient temperature;83%
With iodine; magnesium; benzene
4-nitro-phenol
100-02-7

4-nitro-phenol

Stearoyl chloride
112-76-5

Stearoyl chloride

4-nitrophenyl stearate
14617-86-8

4-nitrophenyl stearate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 1h; Ambient temperature;100%
With triethylamine In tetrahydrofuran at 0℃; for 1h;100%
In 1,4-dioxane; pyridine for 2h; Ambient temperature;65%
With iodine; magnesium; benzene
4-nitro-phenol
100-02-7

4-nitro-phenol

oxalyl dichloride
79-37-8

oxalyl dichloride

p-Nitrophenyl chloroglyoxylate
78974-67-1

p-Nitrophenyl chloroglyoxylate

Conditions
ConditionsYield
for 20h; Heating;100%
for 16h; Heating;
4-nitro-phenol
100-02-7

4-nitro-phenol

N-methylphosphoroamidodichloridate
36598-86-4

N-methylphosphoroamidodichloridate

C7H8ClN2O4P
82960-74-5

C7H8ClN2O4P

Conditions
ConditionsYield
With triethylamine In diethyl ether for 0.5h; Ambient temperature;100%
4-nitro-phenol
100-02-7

4-nitro-phenol

ethylphosphoramidic acid dichloride
61056-26-6

ethylphosphoramidic acid dichloride

C8H10ClN2O4P
82960-75-6

C8H10ClN2O4P

Conditions
ConditionsYield
With triethylamine In diethyl ether at 0℃; for 0.5h;100%
4-nitro-phenol
100-02-7

4-nitro-phenol

propyl-amidophosphoryl chloride
53931-67-2

propyl-amidophosphoryl chloride

C9H12ClN2O4P
82960-76-7

C9H12ClN2O4P

Conditions
ConditionsYield
With triethylamine In diethyl ether at 0℃; for 0.5h;100%
4-nitro-phenol
100-02-7

4-nitro-phenol

fluorodinitroacetonitrile
15562-09-1

fluorodinitroacetonitrile

p-nitrophenyl fluorodinitroacetimidate
75767-62-3

p-nitrophenyl fluorodinitroacetimidate

Conditions
ConditionsYield
In diethyl ether; dichloromethane at 60℃; under 7500600 Torr; for 55h;100%
4-nitro-phenol
100-02-7

4-nitro-phenol

N-Cbz-L-Phe
1161-13-3

N-Cbz-L-Phe

N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester
2578-84-9

N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester

Conditions
ConditionsYield
With N,N'-Bis(2-oxo-3-oxazolidinyl)phosphorodiamidic azide; triethylamine In dichloromethane100%
With pyridine; 2,6-di-tert-butyl-4-methyl-phenol In benzene for 12h;81%
With pyridine; diphenyl hydrogen phosphite; mercury dichloride
4-nitro-phenol
100-02-7

4-nitro-phenol

dabsyl chloride
56512-49-3

dabsyl chloride

4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid 4-nitro-phenyl ester
146303-71-1

4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid 4-nitro-phenyl ester

Conditions
ConditionsYield
With carbonate-bicarbonate buffer In acetone; acetonitrile 1.) 15 min, 2.) reflux;100%
With carbonate-bicarbonate buffer In acetone for 0.5h; Heating;
4-nitro-phenol
100-02-7

4-nitro-phenol

3-<(5-chlorosalicylidene)aminomethyl>benzoic acid

3-<(5-chlorosalicylidene)aminomethyl>benzoic acid

p-nitrophenyl 3-<(5-chlorosalicylidene)aminomethyl>benzoate

p-nitrophenyl 3-<(5-chlorosalicylidene)aminomethyl>benzoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane100%
4-nitro-phenol
100-02-7

4-nitro-phenol

3-<(benzyloxycarbonyl)aminomethyl>benzoic acid
89760-77-0

3-<(benzyloxycarbonyl)aminomethyl>benzoic acid

p-nitrophenyl 3-<(benzyloxycarbonyl)aminomethyl>benzoate
89760-78-1

p-nitrophenyl 3-<(benzyloxycarbonyl)aminomethyl>benzoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide100%
4-nitro-phenol
100-02-7

4-nitro-phenol

<2,6-2H2>-4-nitrophenol
90889-43-3

<2,6-2H2>-4-nitrophenol

Conditions
ConditionsYield
With water-d2; sulfuric acid-d2 at 120℃; for 48h;100%
With water-d2; hydrogen chloride at 175℃; for 0.333333h; Microwave irradiation;82%
With water-d2; hydrogen chloride for 90h; Heating;2.1 g
With sulfuric acid-d2 at 120℃; sealed tube;
4-nitro-phenol
100-02-7

4-nitro-phenol

p-nitrophenolate
14609-74-6

p-nitrophenolate

Conditions
ConditionsYield
With NaH-cryptand<2.2.1) In tetrahydrofuran for 0.00833333h; other reagents, other times, other solvent, other yields;100%
With NaH-cryptand<2.2.1> In tetrahydrofuran for 0.00833333h;100%
With N-butylamine In dimethyl sulfoxide; benzene at 25℃; Equilibrium constant; ionization in solvent mixtures with different ratio;
4-nitro-phenol
100-02-7

4-nitro-phenol

2-(4-(benzyloxy)-1H-indol-3-yl)acetic acid
1464-12-6

2-(4-(benzyloxy)-1H-indol-3-yl)acetic acid

4-Nitrophenyl <(4-Benzyloxy)-1H-indol-3-yl>acetate
144923-56-8

4-Nitrophenyl <(4-Benzyloxy)-1H-indol-3-yl>acetate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane for 1h; Ambient temperature;100%
With dicyclohexyl-carbodiimide In ethyl acetate 1) ice-bath, 1 h, 2) r.t., 18 h;57.7%
4-nitro-phenol
100-02-7

4-nitro-phenol

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

1-(methoxymethoxy)-4-nitrobenzene
880-03-5

1-(methoxymethoxy)-4-nitrobenzene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Cooling with ice;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;89%
(i) NaOEt, EtOH, toluene, (ii) /BRN= 505943/; Multistep reaction;
4-nitro-phenol
100-02-7

4-nitro-phenol

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

1-<(methylthio)methoxy>-4-nitrobenzene
4527-37-1

1-<(methylthio)methoxy>-4-nitrobenzene

Conditions
ConditionsYield
With t-butyl bromide; triethylamine at 35℃; for 24h;100%
4-nitro-phenol
100-02-7

4-nitro-phenol

propargyl bromide
106-96-7

propargyl bromide

1-nitro-4-(prop-2-ynyloxy)benzene
17061-85-7

1-nitro-4-(prop-2-ynyloxy)benzene

Conditions
ConditionsYield
With potassium carbonate In acetone; toluene for 24h; Williamson Ether Synthesis; Reflux;100%
Stage #1: 4-nitro-phenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere;
100%
Stage #1: 4-nitro-phenol With potassium carbonate In acetonitrile at 20℃; for 0.166667h;
Stage #2: propargyl bromide In acetonitrile Reflux;
100%
4-nitro-phenol
100-02-7

4-nitro-phenol

1,1,3,3-tetramethyldisilazane
15933-59-2

1,1,3,3-tetramethyldisilazane

Dimethyl-(4-nitro-phenoxy)-silane
79516-20-4

Dimethyl-(4-nitro-phenoxy)-silane

Conditions
ConditionsYield
100%
at 20 - 160℃; for 2h; Inert atmosphere;

100-02-7Relevant articles and documents

Catalytic degradation of an organophosphorus agent at Zn-OH sites in a metal-organic framework

Mian, Mohammad Rasel,Islamoglu, Timur,Afrin, Unjila,Goswami, Subhadip,Cao, Ran,Kirlikovali, Kent O.,Hall, Morgan G.,Peterson, Gregory W.,Farha, Omar K.

, p. 6998 - 7004 (2020)

Chemical warfare agents (CWAs), and in particular organophosphorus nerve agents, still pose a significant threat to society due to their continued use despite international bans. While nature has constructed a variety of enzymes that are capable of rapidly hydrolyzing organophosphorus substrates, the poor stability of enzymes outside of buffered solutions has limited their use in practical applications, such as in filters or on protective suits. As a result, we have explored the use of metal-organic frameworks (MOFs) as robust and tunable catalytic materials in which the nodes can be tailored to resemble the active sites found in these enzymes. We identified the Zn-based MOF, MFU-4l, as a promising hydrolysis catalyst due to the presence of Zn(II)-OH groups on the nodes, which are structurally reminiscent of the active sites in carbonic anhydrase (CA), a Zn-based enzyme that has been shown to efficiently catalyze the hydrolysis of phosphate esters. Indeed, MFU-4l can rapidly hydrolyze both the organophosphorus nerve agent, GD, and its simulant, DMNP, with half-lives as low as 1 min, which is competitive with the some of best heterogeneous hydrolysis catalysts reported to date.

Biomimicking, metal-chelating and surface-imprinted polymers for the degradation of pesticides

Erdem, Murat,Say, Ridvan,Ers?z, Arzu,Denizli, Adil,Türk, Hayrettin

, p. 238 - 243 (2010)

Molecularly imprinted polymer beads (PIBs) and non-imprinted (control) polymer beads (NIBs) have been prepared from methacryloylhistidine-Co2+, -Ni2+, and -Zn2+ monomers and applied as catalyst in the hydrolysis of paraoxo

Guanidine based self-assembled monolayers on Au nanoparticles as artificial phosphodiesterases

Salvio, Riccardo,Cincotti, Antonio

, p. 28678 - 28682 (2014)

Gold nanoparticles passivated with a long chain alkanethiol decorated with a phenoxyguanidine moiety were prepared and investigated as catalysts in the cleavage of the RNA model compound HPNP and diribonucleoside monophosphates. The catalytic efficiency and the high effective molarity value of the Au monolayer protected colloids points to a high level of cooperation between the catalytic groups.

A unique nickel system having versatile catalytic activity of biological significance

Chattopadhyay, Tanmay,Mukherjee, Madhupama,Mondal, Arindam,Maiti, Pali,Banerjee, Arpita,Banu, Kazi Sabnam,Bhattacharya, Santanu,Roy, Bappaditya,Chattopadhyay,Mondai, Tapan Kumar,Nethaji, Munirathinam,Zangrando, Ennio,Das, Debasis

, p. 3121 - 3129 (2010)

A new dinuclear nickel(ll) complex, [Ni2(LH2)(H 2O)2(OH)(NO3)](NO3)3 (1), of an "end-off" compartmental ligand 2,6-bis(N-ethylpiperazine- iminomethyl)-4-methyl-phenolato, has been synthesized and structurally characterized. The X-ray single crystal structure analysis shows that the piperazine moieties assume the expected chair conformation and are protonated. The complex 1 exhibits versatile catalytic activities of biological significance, viz. catecholase, phosphatase, and DNA cleavage activities, etc. The catecholase activity of the complex observed is very dependent on the nature of the solvent. In acetonitrile medium, the complex is inactive to exhibit catecholase activity. On the other hand, in methanol, it catalyzes not only the oxidation of 3,5-ditert-buty !catechol (3,5-DTBC) but also tetrachlorocatechol (TCC), a catechol which is very difficult to oxidize, under aerobic conditions. UV-vis spectroscopic investigation shows that TCC oxidation proceeds through the formation of an intermediate. The intermediate has been characterized by an electron spray ionizaton-mass spectrometry study, which suggests a bidentate rather than a monodentate mode of TCC coordination in that intermediate, and this proposition have been verified by density functional theory calculation. The complex also exhibits phosphatase (with substrate p-nitrophenylphosphate) and DNA cleavage activities. The DNA cleavage activity exhibited by complex 1 most probably proceeds through a hydroxyl radical pathway. The bioactivity study suggests the possible applications of complex 1 as a site specific recognition of DNA and/or as an anticancer agent.

Mesoporous zeolites as enzyme carriers: Synthesis, characterization, and application in biocatalysis

Mitchell, Sharon,Pérez-Ramírez, Javier

, p. 28 - 37 (2011)

We study the application of hierarchical ZSM-5 zeolites, combining micropores and intracrystalline mesopores, as carriers for lipase enzymes compared with purely microporous ZSM-5 and mesoporous MCM-41. Strategies to improve enzyme immobilization by modif

Organoruthenium(II) compounds with pyridyl benzoxazole/benzthiazole moiety: studies on DNA/protein binding and enzyme mimetic activities

Gomathi, Asaithambi,Vijayan, Paranthaman,Viswanathamurthi, Periasamy,Suresh, Shanmugam,Nandhakumar, Raju,Hashimoto, Takeshi

, p. 1645 - 1666 (2017)

We report herein synthesis and characterization of four new organoruthenium(II) complexes of the type [RuH(CO)(PPh3)2(L1,2)]Cl (1, 3) and [Ru(CO)(Cl)2(AsPh3)(L1,2)] (2, 4) derived from the reaction of [RuHCl(CO)(EPh3)3] (E?=?P or As) with 2-(pyridine-2yl)benzoxazole (L1) and 2-(pyridine-2yl)benzthiazole (L2). Single-crystal X-ray diffraction data of 2 proved octahedral geometry of the complexes with a 1 : 1 ratio between the metal and the coordinated ligands. The binding affinities of 1–4 toward calf-thymus DNA (CT-DNA) and BSA were thoroughly studied by various spectroscopic techniques. Furthermore, the coordination compounds exhibit catecholase-like activities in the aerial oxidation of 3,5-di-tert-butylcatechol to the corresponding o-quinone and phosphatase-like activities in the hydrolysis of 4-nitrophenyl phosphate to 4-nitrophenolate ion. The kinetic parameters have been determined using Michaelis–Menten approach. The highest kcat values suggested that coordination compounds exhibit higher rates of catalytic efficacy.

Iron-catalyzed conversion of unactivated aryl halides to phenols in water

Ren, Yunlai,Cheng, Lin,Tian, Xinzhe,Zhao, Shuang,Wang, Jianji,Hou, Chaodong

, p. 43 - 45 (2010)

Although iron is low-cost and environmentally friendly, there is no report about iron-catalyzed conversion of unactivated aryl halides to phenols. In this Letter, a new method for the present conversion was developed with iron compounds as the catalyst and water as the solvent. The suggested method allowed a series of unactivated aryl bromides and aryl iodides to be converted into the corresponding substituted phenols in moderate to high yields.

Antibody catalyzed modification of amino acids. Efficient hydrolysis of tyrosine benzoate

Benedetti,Berti,Colombatti,Flego,Gardossi,Linda,Peressini

, p. 715 - 716 (2001)

Esterase antibody 522c2, the first example of a catalytic antibody specifically programmed to control the reactivity of functional groups on the side chain of tyrosine, accelerates the hydrolysis of benzoate esters of L-tyrosine and tyrosine-containing dipeptides by a factor of 104 and is moderately active against other benzoate esters.

Insights into Catalytic Hydrolysis of Organophosphonates at M-OH Sites of Azolate-Based Metal Organic Frameworks

Cao, Ran,Chen, Haoyuan,Farha, Omar K.,Islamoglu, Timur,Kirlikovali, Kent O.,Mian, Mohammad Rasel,Snurr, Randall Q.

, p. 9893 - 9900 (2021)

Organophosphorus nerve agents, a class of extremely toxic chemical warfare agents (CWAs), have remained a threat to humanity because of their continued use against civilian populations. To date, Zr(IV)-based metal organic framework (MOFs) are the most pre

Influence of Water Structure on Solvolysis in Water-in-Oil Microemulsions

Garcia-Rio, L.,Leis, J. R.,Iglesias, E.

, p. 12318 - 12326 (1995)

The kinetics of solvolysis of diphenylmethyl chloride, 4-nitrophenyl chloroformate, benzoyl chloride, p-anisoyl chloride, and bis(4-nitrophenyl)carbonate in water/AOT/isooctane microemulsions with various water/surfactant mole ratios W (AOT = sodium bis(2-ethylhexyl)sulfosuccinate) were interpreted by using a pseudophase model in which the substrates are assumed to be distributed between the isooctane and interface phases.The W-dependence of the intrinsic rate constants k for solvolysis at the interface depends on the solvolysis mechanism: for SN1 reactions, k decreased with W, which is attributed to decreasing polarity of the interface; contrariwise, SN2 reactions are accelerated by decreasing W, which is attributed to increasing nucleophilicity of interfacial water.

Hydrolysis of nitrophenyl esters catalyzed by modified cyclodextrin in water pools in reversed micelles

Nakamura,Sugama

, p. 4682 - 4685 (1984)

-

Isolation and characterization of a beta-primeverosidase-like endo-manner beta-glycosidase from Aspergillus fumigatus AP-20.

Yamamoto, Shigeru,Okada, Masamichi,Usui, Taichi,Sakata, Kanzo

, p. 801 - 807 (2002)

A novel beta-glycosidase-producing microorganism was isolated from soil and identified as Aspergillus fumigatus AP-20 based on its taxonomical characteristics. The enzyme was found to be an extracellular protein in the culture of the isolated fungus and w

A strategic approach of enzyme engineering by attribute ranking and enzyme immobilization on zinc oxide nanoparticles to attain thermostability in mesophilic Bacillus subtilis lipase for detergent formulation

Khan, Mohd Faheem,Kundu, Debasree,Hazra, Chinmay,Patra, Sanjukta

, p. 66 - 82 (2019)

The present study envisaged rationalized protein engineering approach to attain thermostability in a mesophilic Bacillus subtilis lipase. Contributing amino acids for thermostability were analyzed from homologous thermophilic-mesophilic protein dataset th

Cellular zwitterionic metabolite analogs simultaneously enhance reaction rate, thermostability, salt tolerance, and substrate specificity of α-glucosidase

Deguchi, Eisuke,Koumoto, Kazuya

, p. 3128 - 3134 (2011)

We investigated the structural effects of metabolite analogs derived from a naturally-occurring zwitterionic metabolite, glycine betaine, on the activity of several hydrolases. The initial velocities of the hydrolases were enhanced by the addition of the

Kinetics and speciation of paraoxon hydrolysis by zinc(II)-azamacrocyclic catalysts

Kennedy, Daniel J.,Mayer, Brian P.,Baker, Sarah E.,Valdez, Carlos A.

, p. 123 - 131 (2015)

Four Zn2+-azamacrocyclic complexes were investigated for their ability to catalyze the hydrolysis of the toxic organophosphate (OP) pesticide diethyl paraoxon. Of the four complexes studied, Zn2+-1,5,9-triazacyclododecane (Zn2+-[12]aneN3) was found to be the most effective catalyst with a pseudo-first order reaction rate of k = 6.08 ± 0.23 × 10-4 min-1. Using 31P nuclear magnetic resonance (NMR) spectroscopy, the two products diethyl phosphate (DEP) and ethyl (4-nitrophenyl) phosphate (E4NPP) were identified for both catalyzed and background hydrolysis of paraoxon. Reaction rate and selectivity for formation of the non-toxic DEP were observed to correlate with catalyst pKa. The rate of formation of toxic E4NPP, however, was independent of both the presence and nature of the catalyst. The potential roles of buffer concentration and product inhibition were also investigated. Background hydrolysis at elevated reaction temperatures (50°C) displayed no preference for DEP over that of E4NPP despite substantial differences between the characteristics (i.e., pKa values) of the two leaving groups (ethoxide vs. 4-nitrophenoxide anions). As with previous observations of these types of metal-catalyzed hydrolyses, we invoke the formation of a trigonal bipyramidal-like transition state involving a Zn-coordinated phosphate bond, with the leaving group at the apical position and the incoming HO- anion approaching from the opposite end. Kinetic rates for catalytic hydrolysis display an overwhelming propensity for DEP formation, and suggest the importance of steric restrictions on transition state structure, namely a concerted arrangement of the azamacrocycle in opposition to the bulky 4-nitrophenoxy group.

Rationally Designed Double-Shell Dodecahedral Microreactors with Efficient Photoelectron Transfer: N-Doped-C-Encapsulated Ultrafine In2O3 Nanoparticles

Sun, Liming,Li, Rong,Zhan, Wenwen,Wang, Fan,Zhuang, Yuan,Wang, Xiaojun,Han, Xiguang

, p. 3053 - 3060 (2019)

It is desirable but challenging to design efficient micro-/nanoreactors for chemical reactions. In this study, we have fabricated mesoporous double-shelled hollow microreactors composed of N-doped-C-coated ultrafine In2O3 nanoparticles [N-C/In2O3 HD (hollow dodecahedron)] by the thermolysis of a dodecahedral In-based framework in Ar atmosphere. The obtained N-C/In2O3 HD exhibited excellent activity in the photocatalytic oxidative hydroxylation of a series of arylboronic acid substrates. This property can be attributed to its enhanced optical absorption and efficient separation of photo-generated electron–hole pairs, imparted by the unique structure and uniformly coated N-doped C layers. Furthermore, we found O2.? to be the critical active species in the process of photocatalytic oxidative hydroxylation of arylboronic acids, and the formation mechanism of this radical is also proposed. Theoretical calculations further confirmed that the N-doped C layer serves as an electron acceptor and revealed the microscopic charge-carrier migration path through the In2O3/N-doped graphite interfaces. Thus, photo-generated electrons from hybrid states of In2O3, composed of In 5s and 2p orbitals, are transferred into the hybrid states of N-doped graphite, composed of C 2p and N 2p orbitals. The present study may be helpful for understanding and designing carbon-based micro-/nanoreactors for photocatalytic reactions, and may also be useful for investigating related micro-/nanoreactors.

Use of MoO2Cl2(DMF)2 as a precursor for molybdate promoted hydrolysis of phosphoester bonds

Tome, Catia M.,Oliveira, M. Conceicao,Pillinger, Martyn,Goncalves, Isabel S.,Abrantes, Marta

, p. 3901 - 3907 (2013)

Phosphoester bond cleavage of para-nitrophenylphosphate (pNPP), a commonly used model substrate, is accelerated by using the complex MoO2Cl 2(DMF)2 (1) (DMF = dimethylformamide) as a hydrolysis promoting agent, even when c

Enzyme shielding in an enzyme-thin and soft organosilica layer

Correro, M. Rita,Moridi, Negar,Schützinger, Hansj?rg,Sykora, Sabine,Ammann, Erik M.,Peters, E. Henrik,Dudal, Yves,Corvini, Philippe F.-X.,Shahgaldian, Patrick

, p. 6285 - 6289 (2016)

The fragile nature of most enzymes is a major hindrance to their use in industrial processes. Herein, we describe a synthetic chemical strategy to produce hybrid organic/inorganic nanobiocatalysts; it exploits the self-assembly of silane building blocks at the surface of enzymes to grow an organosilica layer, of controlled thickness, that fully shields the enzyme. Remarkably, the enzyme triggers a rearrangement of this organosilica layer into a significantly soft structure. We demonstrate that this change in stiffness correlates with the biocatalytic turnover rate, and that the organosilica layer shields the enzyme in a soft environment with a markedly enhanced resistance to denaturing stresses. Important soft skills: Hybrid organic/inorganic nanobiocatalysts were created by the immobilization of enzymes on amino-modified silica nanoparticles and subsequent self-assembly and polycondensation of silane building blocks at the surface of the enzymes. The soft environment of the organosilica layer shielded the enzymes from denaturing stresses; however, the enzymes retained their conformational freedom and thus their catalytic activity (see picture).

Mesoporous Core-Shell Nanostructures Bridging Metal and Biocatalyst for Highly Efficient Cascade Reactions

Gao, Jing,Gao, Shiqi,Jiang, Yanjun,Liu, Yunting,Ma, Li,Wang, Zihan

, p. 1375 - 1380 (2020)

Mesoporous core-shell structured nanocatalysts with a PdPt bimetallic core and enzyme-immobilized polydopamine (PDA) shell were designed, in which the PDA shell worked as a barrier to position the bimetallic core and enzyme in separated locations. The accessible mesoporous structures of both the core and shell significantly facilitate mass transfer and catalyst utilization, improving the synergistic catalytic abilities in cascade reactions. The obtained bifunctional nanocatalysts enabled efficient two-step one-pot cascade reactions of different types: dynamic kinetic resolution of primary amines in organic solvent with high yield and enantioselectivity (up to 99% yield and 98% ee) and degradation of organophosphate nerve agent in aqueous solution with high rate constant and turnover frequency number values (0.8 min-1 and 20 min-1, respectively).

The mechanism by which 4-hydroxy-2,2,6,6-tetramethylpiperidene-1-oxyl (tempol) diverts peroxynitrite decomposition from nitrating to nitrosating species

Bonini, Marcelo G.,Mason, Ronald P.,Augusto, Ohara

, p. 506 - 511 (2002)

Tempol is a stable nitroxide radical that has been shown to protect laboratory animals from the injury associated with conditions of oxidative and nitrosoactive stress. Tempol's protective mechanisms against reactive oxygen species have been extensively studied, but its interactions with reactive nitrogen species remain little explored. Recently, it has been shown that tempol is a potent inhibitor of peroxynitrite-mediated phenol nitration while it increases phenol nitrosation by a complex mechanism [Carrol et al. (2000) Chem. Res. Toxicol. 13, 294]. To obtain further mechanistic insights, we reexamined the interaction of peroxynitrite with tempol in the absence and presence of carbon dioxide. Stopped-flow kinetic studies confirmed that tempol does not react directly with peroxynitrite but levels off the amount of oxygen (monitored with an oxygen electrode) and nitrite (monitored by chemiluminescence) produced from peroxynitrite in the presence and absence of carbon dioxide to about 30% and 70% of the initial oxidant concentration at pH 5.4, 6.4, and 7.4. Tempol inhibited phenol nitration while increasing the amounts of 4-nitrosophenol, that attained yields close to 30% of the peroxynitrite in the presence of carbon dioxide at pH 7.4. Fast-flow EPR experiments showed detectable changes in the instantaneous tempol concentration (maximum of 15%) only in the presence of carbon dioxide. Under these conditions, the instantaneous concentration of the carbonate radical anion was reduced by tempol in a concentration-dependent manner. The results indicate that tempol is oxidized by peroxynitrite-derived radicals (·OH and CO3·-, in the absence and presence of carbon dioxide, respectively) to the oxoammonium cation which, in turn, is reduced back to tempol while oxidizing peroxynitrite to oxygen and nitric oxide. The latter reacts rapidly with peroxynitrite-derived nitrogen dioxide to produce the nitrosating species, dinitrogen trioxide. Overall, the results support a role for peroxynitrite and its derived radicals in the tissue pathology associated with inflammatory conditions.

Inhibition of Yersinia protein tyrosine phosphatase by phosphonate derivatives of calixarenes

Vovk, Andriy I.,Kononets, Lyudmyla A.,Tanchuk, Vsevolod Yu.,Cherenok, Sergiy O.,Drapailo, Andriy B.,Kalchenko, Vitaly I.,Kukhar, Valery P.

, p. 483 - 487 (2010)

Inhibition of Yersinia protein tyrosine phosphatase by calix[4]arene mono-, bis-, and tetrakis(methylenebisphosphonic) acids as well as calix[4]arene and thiacalix[4]arene tetrakis(methylphosphonic) acids have been investigated. The kinetic studies reveal

Functional characterization of salt-tolerant microbial esterase WDEst17 and its use in the generation of optically pure ethyl (R)-3-hydroxybutyrate

Wang, Yilong,Xu, Yongkai,Zhang, Yun,Sun, Aijun,Hu, Yunfeng

, p. 769 - 776 (2018)

The two enantiomers of ethyl 3-hydroxybutyrate are important intermediates for the synthesis of a great variety of valuable chiral drugs. The preparation of chiral drug intermediates through kinetic resolution reactions catalyzed by esterases/lipases has been demonstrated to be an efficient and environmentally friendly method. We previously functionally characterized microbial esterase PHE21 and used PHE21 as a biocatalyst to generate optically pure ethyl (S)-3-hydroxybutyrate. Herein, we also functionally characterized one novel salt-tolerant microbial esterase WDEst17 from the genome of Dactylosporangium aurantiacum subsp. Hamdenensis NRRL 18085. Esterase WDEst17 was further developed as an efficient biocatalyst to generate (R)-3-hydroxybutyrate, an important chiral drug intermediate, with the enantiomeric excess being 99% and the conversion rate being 65.05%, respectively, after process optimization. Notably, the enantio-selectivity of esterase WDEst17 was opposite than that of esterase PHE21. The identification of esterases WDEst17 and PHE21 through genome mining of microorganisms provides useful biocatalysts for the preparation of valuable chiral drug intermediates.

β-D-GLUCOSIDASE-CATALYSED TRANSFER OF THE GLYCOSYL GROUP FROM ARYL β-D-GLUCO- AND β-D-XYLO-PYRANOSIDES TO PHENOLS

Aerts, Guido M.,Opstal, Omer Van,Bruyne, Clement K. De

, p. 221 - 234 (1982)

The effect of phenols on the hydrolysis of substituted phenyl β-D-gluco- and β-D-xylo-pyranosides by β-D-glucosidase from Stachybotrys atra has been investigated.Depending on the glycon part of the substrate and on the phenol substituent, the hydrolysis is either inhibited or activated.With aryl β-D-glucopyranosides, such transfer does not occur when phenols are used as acceptors, but it does occur with anilines.A two-steps mechanism, in which the first step is partially reversible, is proposed to explain these observations.A qualitative analysis of the various factors determing the overall effect of the phenol is given.

Evolution of metal complex-catalysts by dynamic templating with transition state analogs

Matsumoto, Masaomi,Estes, Deven,Nicholas, Kenneth M.

, p. 1847 - 1852 (2010)

The elicitation of hydrolytic catalysts from a dynamic library of imine-zinc(II) complexes (and their precursor aldehydes and amines) via templating with pro-transition state analogs (pro-TSA) is described. pro-TSA (2-pyridyl)phosphonate 2 amplifies a ben

Isoenzymes of pig-liver esterase reveal striking differences in enantioselectivities

Hummel, Anke,Bruesehaber, Elke,Boettcher, Dominique,Trauthwein, Harald,Doderer, Kai,Bornscheuer, Uwe T.

, p. 8492 - 8494 (2007)

(Graph Presented) An esterase toolbox: A set of isoenzymes of pig liver esterases (PLE) is identified, cloned, and overexpressed in E. coli. They show striking differences in enantioselectivity and enantiopreference in the kinetic resolution of acetates o

A Mechanistic Study on the Non-enzymatic Hydrolysis of Kdn Glycosides

Nejatie, Ali,Colombo, Cinzia,Hakak-Zargar, Benyamin,Bennet, Andrew J.

supporting information, (2022/01/13)

Sialic acids are biologically important carbohydrates that are prevalent throughout nature. We are interested in their intrinsic reactivity in aqueous solution and how such reactivity affects the design of substrates for investigation of enzymes that process these sugars. To probe the reactivity differences between two sialic acid family members N-acetylneuraminic acid and Kdn we measured the rate constants for hydrolysis of 4-nitrophenyl 3-deoxy-d-glycero-α-d-galacto-non-2-ulosonide in aqueous solution. The kinetic data is consistent with glycosidic C?O bond cleavage occurring via four mechanistic pathways, and these are: (i) hydronium ion-catalyzed hydrolysis of the neutral sugar; (ii) hydronium ion-catalyzed hydrolysis of the glycosidic carboxylate; (iii) water-catalyzed hydrolysis of the anionic glycoside; and (iv) base-promoted reaction of the anionic glycoside. To study the effects of C-5 substitution on the Kdn glycoside we made 4-nitrophenyl 5-O-methyl-α-Kdn glycoside and determined its rate constants for hydrolysis. All hydrolytic rate constants for both Kdn glycosides were larger than those reported for the parent N-acetyl-α-neuraminide. The water-catalyzed reaction (pathway iii) exhibited a βlg value of ?1.3±0.1. We conclude that the larger rate constants associated with C5-oxygen containing sialosides results from less steric congestion at the hydrolytic transition states than for the parent C-5 acetamido glycoside.

A copper nitride catalyst for the efficient hydroxylation of aryl halides under ligand-free conditions

Mitsudome, Takato,Mizugaki, Tomoo,Xu, Hang,Yamaguchi, Sho

supporting information, p. 6593 - 6597 (2021/08/10)

Copper nitride (Cu3N) was used as a heterogeneous catalyst for the hydroxylation of aryl halides under ligand-free conditions. The cubic Cu3N nanoparticles showed high catalytic activity, comparable to those of conventional Cu catalysts with nitrogen ligands, demonstrating that the nitrogen atoms in Cu3N act as functional ligands that promote hydroxylation.

Biochemical and biophysical characterisation of a small purified lipase from Rhizopus oryzae ZAC3

Ayinla, Zainab A.,Ademakinwa, Adedeji N.,Gross, Richard A.,Agboola, Femi K.

, (2021/02/16)

The characteristics of a purified lipase from Rhizopus oryzae ZAC3 (RoL-ZAC3) were investigated. RoL-ZAC3, a 15.8 kDa protein, which was optimally active at pH 8 and 55 °C had a half-life of 126 min at 60 °C. The kinetic parameters using p-nitrophenylbuty

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