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4-Nitrophenol, also known as p-nitrophenol or 4-hydroxynitrobenzene, is a phenolic compound characterized by the presence of a nitro group at the opposite position of the hydroxyl group on the benzene ring. It exists in two polymorphic forms: the colorless, unstable alpha form and the yellow, stable beta form. 4-Nitrophenol is a yellow to tan crystalline solid or powder, which is not steam volatile and is more soluble in water than its ortho isomer. It is used in various applications due to its chemical properties and reactivity.

100-02-7 Suppliers

This product is a nationally controlled contraband or patented product, and the Lookchem platform doesn't provide relevant sales information.
  • 100-02-7 Structure
  • Basic information

    1. Product Name: p-nitrophenol
    2. Synonyms: Phenol,p-nitro- (8CI);1-Hydroxy-4-nitrobenzene;4-Hydroxy-1-nitrobenzene;4-Hydroxynitrobenzene;Phenol, 4-nitro-;Niphen;p-Hydroxynitrobenzene;p-Nitrophenol;
    3. CAS NO:100-02-7
    4. Molecular Formula: C6H5NO3
    5. Molecular Weight: 138.1014
    6. EINECS: 202-811-7
    7. Product Categories: Aromatics;Analytical Chemistry;Biochemistry;Coupling Reactions (Peptide Synthesis);Indicator (pH);Peptide Synthesis;pH Indicators;Organics;Phenoles and thiophenoles;Nitro;dye intermediates, pharmaceutical and pesticide
    8. Mol File: 100-02-7.mol
  • Chemical Properties

    1. Melting Point: 112-114℃
    2. Boiling Point: 279 °C at 760 mmHg
    3. Flash Point: 141.9 °C
    4. Appearance: Yellow to brown crystals
    5. Density: 1.395 g/cm3
    6. Vapor Pressure: 0.00243mmHg at 25°C
    7. Refractive Index: 1.5723 (estimate)
    8. Storage Temp.: Store in dark!
    9. Solubility: ethanol: soluble95%, clear, dark yellow (100 mg/mL)
    10. PKA: 7.15(at 25℃)
    11. Water Solubility: 1.6 g/100 mL (25℃)
    12. Stability: Stable. Incompatible with strong oxidizing agents, strong bases, organics, combustible material, reducing agents. Combustible.
    13. Merck: 14,6620
    14. BRN: 1281877
    15. CAS DataBase Reference: p-nitrophenol(CAS DataBase Reference)
    16. NIST Chemistry Reference: p-nitrophenol(100-02-7)
    17. EPA Substance Registry System: p-nitrophenol(100-02-7)
  • Safety Data

    1. Hazard Codes:  Xn:Harmful;
    2. Statements: R20/21/22:; R33:;
    3. Safety Statements: S28A:;
    4. RIDADR: UN 1663 6.1/PG 3
    5. WGK Germany: 2
    6. RTECS: SM2275000
    7. F: 8
    8. TSCA: Yes
    9. HazardClass: 6.1
    10. PackingGroup: III
    11. Hazardous Substances Data: 100-02-7(Hazardous Substances Data)

100-02-7 Usage

Uses

1. Used in Pharmaceutical Synthesis:
4-Nitrophenol is used as a key intermediate in the manufacturing of drugs such as acetaminophen, which is an analgesic and antipyretic medication.
2. Used in Fungicide and Insecticide Production:
4-Nitrophenol is utilized as a starting material for the synthesis of fungicides, insecticides like methyl and ethyl parathion, and other pesticides, contributing to its role in agricultural applications.
3. Used in Dye Manufacturing:
4-Nitrophenol serves as a precursor in the production of various dyes, highlighting its importance in the chemical industry.
4. Used as a Wood Preservative:
Due to its fungicidal and bactericidal properties, 4-Nitrophenol is employed as a wood preservative to protect against decay and infestation.
5. Used as a Chemical Indicator:
4-Nitrophenol is used as an indicator in a 0.1% alcohol solution, with a pH range of 5.6 (colorless) to 7.6 (yellow), making it a valuable tool in chemical analysis and research.
6. Used in Cytochrome P450 2E1 Experiments:
4-Nitrophenol acts as a substrate for experiments on cytochrome P450 2E1, an enzyme involved in the metabolism of various drugs and toxins, further emphasizing its significance in biological and medical research.

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.

Synthesis Reference(s)

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

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

100-02-7SDS

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.

Influence of activated carbons on the kinetics and mechanisms of aromatic molecules ozonation

Merle,Pic,Manero,Mathé,Debellefontaine

, p. 166 - 172 (2010)

Companies have been looking for new methods for treating toxic or refractory wastewaters; which can mainly be used prior to or after or in connexion with biological treatment processes. This paper compares conventional ozone oxidation with activated carbon (AC) promoted ozone oxidation, which helps developing a mechanism involving HO{radical dot} radical. For a compound which is quite easy to oxidise, like 2,4-dichlorophenol (2,4-DCP) conventional ozonation is efficient enough to remove the initial molecule. The mechanism involved mainly consists of an electrophilic attack on the aromatic ring, which is activated by the donor effect of the -OH group, then followed by a 1,3 dipolar cycloaddition (Criegee mechanism) that leads to aliphatic species, mainly carboxylic acids. Yet, the addition of AC, through the presence of HO{radical dot} radical, enhances the removal of these species which are more refractory. For a refractory compound like nitrobenzene (NB), with a de-activated aromatic ring because of the attractive effect of -NO2, conventional ozonation is inefficient. On the contrary, this molecule can be quite easily removed with AC promoted oxidation and it is found that the mechanism (electrophilic attack followed by a 1,3 dipolar cycloaddition) is quite similar to the one corresponding to conventional ozonation, but with less selectivity. For both molecules, a mass balance has established that the by-products accounting for more than 75% of the remaining COD can be quantified. A significant part is composed of carboxylic acids (acetic, oxalic, etc.), which could afterwards be easily removed in an industrial wastewater treatment process followed by a final biological treatment step.

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

A simple DNase model system comprising a dinuclear Zn(II) complex in methanol accelerates the cleavage of a series of methyl aryl phosphate diesters by 1011-1013

Neverov, Alexei A.,Liu, C. Tony,Bunn, Shannon E.,Edwards, David,White, Christopher J.,Melnychuk, Stephanie A.,Brown, R. Stan

, p. 6639 - 6649 (2008)

The di-Zn(II) complex of 1,3-bis[N1,N′1-(1,5,9- triazacyclododecyl)]propane with an associated methoxide (3:Zn(II) 2:-OCH3) was prepared and its catalysis of the methanolysis of a series of fourteen methyl aryl phosphate diesters (6) was studied at sspH 9.8 in methanol at 25.0 ± 0.1°C. Plots of kobs vs [3:Zn(II)2: -OCH3]free for all members of 6 show saturation behavior from which KM and kcatmax were determined. The second order rate constants for the catalyzed reactions (k catmax/KM) for each substrate are larger than the corresponding methoxide catalyzed reaction (k2-OMe) by 1.4 × 108 to 3 × 109-fold. The values of kcatmax for all members of 6 are between 4 × 10 11 and 3 × 1013 times larger than the solution reaction at sspH 9.8, with the largest accelerations being given for substrates where the departing aryloxy unit contains ortho-NO 2 or C(=O)OCH3 groups. Based on the linear Bronsted plots of kcatmax vs sspK aof the phenol, βIg values of -0.57 and -0.34 are determined respectively for the catalyzed methanolysis of regular substrates that do not contain the ortho-NO2 or C(=O)OCH3 groups, and those substrates that do. The data are consistent with a two step mechanism for the catalyzed reaction with rate limiting formation of a catalyst-coordinated phosphorane intermediate, followed by fast loss of the aryloxy leaving group. A detailed energetics calculation indicates that the catalyst binds the transition state comprising [CH3O -:6]?, giving a hypothetical [3:Zn(II) 2:CH3O-:6]? complex, by -21.4 to -24.5 kcal/mol, with the strongest binding being for those substrates having the ortho-NO2 or C(=O)OCH3 groups.

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.

Structural flexibility enhances the reactivity of the bioremediator glycerophosphodiesterase by fine-tuning its mechanism of hydrolysis

Hadler, Kieran S.,Mitic, Natasa,Ely, Fernanda,Hanson, Graeme R.,Gahan, Lawrence R.,Larrabee, James A.,Ollis, David L.,Schenk, Gerhard

, p. 11900 - 11908 (2009)

The glycerophosphodiesterase from Enterobacter aerogenes (GpdQ) belongs to the family of binuclear metallohydrolases and has attracted recent attention due to its potential in bioremediation. Formation of a catalytically competent binuclear center is prom

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.

Designed four-helix bundle catalysts - The engineering of reactive sites for hydrolysis and transesterification reactions of p-nitrophenyl esters

Baltzer, Lars,Broo, Kerstin S.,Nilsson, Helena,Nilsson, Jonas

, p. 83 - 91 (1999)

Four-helix bundle proteins have been designed that catalyze the hydrolysis and transesterification reactions of p-nitrophenyl esters by a cooperative nucleophilic and general acid mechanism. The catalysts consist of two 42-residue peptides that fold into

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

Isotope effects and medium effects on sulfuryl transfer reactions

Hoff,Larsen,Hengge

, p. 9338 - 9344 (2001)

Kinetic isotope effects and medium effects have been measured for sulfuryl-transfer reactions of the sulfate ester p-nitrophenyl sulfate (pNPS). The results are compared to those from previous studies of phosphoryl transfer, a reaction with mechanistic similarities. The N-15 and the bridge O-18 isotope effects for the reaction of the pNPS anion are very similar to those of the p-nitrophenyl phosphate (pNPP) dianion. This indicates that in the transition states for both reactions the leaving group bears nearly a full negative charge resulting from a large degree of bond cleavage to the leaving group. The nonbridge O-18 isotope effects support the notion that the sulfuryl group resembles SO3 in the transition state. The reaction of the neutral pNPS species in acid solution is mechanistically similar to the reaction of the pNPP monoanion. In both cases proton transfer from a nonbridge oxygen atom to the leaving group is largely complete in the transition state. Despite their mechanistic similarities, the phosphoryl- and sulfuryl-transfer reactions differ markedly in their response to medium effects. Increasing proportions of the aprotic solvent DMSO to aqueous solutions of pNPP cause dramatic rate accelerations of up to 6 orders of magnitude, but only a 50-fold rate increase is observed for pNPS. Similarly, phosphoryl transfer from the pNPP dianion to tert-amyl alcohol is 9000-fold faster than the aqueous reaction, while the sulfuryl transfer from the pNPS anion is some 40-fold slower. The enthalpic and entropic contributions to these differing medium effects have been measured and compared.