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4-Nitroacetophenone is a member of the acetophenones class, specifically an acetophenone derivative substituted at the para-position by a nitro group. It is a C-nitro compound and appears as yellow prisms or bright yellow powder. The pure product is a pale yellow crystal or needle crystal, soluble in hot ethanol, ether, and benzene, but insoluble in water. It serves as a raw material for the manufacture of synthomycin and chloramphenicol.

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  • 100-19-6 Structure
  • Basic information

    1. Product Name: p-Nitroacetophenone
    2. Synonyms: Ethanone, 1-(4-nitrophenyl)-;Ethanone,1-(4-nitrophenyl)-;Methyl4-nitrophenylketone;Methyl-p-nitrophenyl ketone;methyl-p-nitrophenylketone;Methylp-nitrophenylketone;p-Acetylnitrobenzene;Paranitroacetophenone
    3. CAS NO:100-19-6
    4. Molecular Formula: C8H7NO3
    5. Molecular Weight: 165.15
    6. EINECS: 202-827-4
    7. Product Categories: Aromatic Acetophenones & Derivatives (substituted);C7 to C8;Carbonyl Compounds;Ketones;Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
    8. Mol File: 100-19-6.mol
    9. Article Data: 484
  • Chemical Properties

    1. Melting Point: 75-78 °C(lit.)
    2. Boiling Point: 202 °C(lit.)
    3. Flash Point: 201-202°C
    4. Appearance: Yellow/Crystalline Powder
    5. Density: 1.3450 (rough estimate)
    6. Vapor Pressure: 0.00511mmHg at 25°C
    7. Refractive Index: 1.5468 (estimate)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: N/A
    10. Water Solubility: Insoluble in water.
    11. BRN: 607777
    12. CAS DataBase Reference: p-Nitroacetophenone(CAS DataBase Reference)
    13. NIST Chemistry Reference: p-Nitroacetophenone(100-19-6)
    14. EPA Substance Registry System: p-Nitroacetophenone(100-19-6)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 36-22
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS: AM9627000
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 100-19-6(Hazardous Substances Data)

100-19-6 Usage

Uses

Used in Pharmaceutical Synthesis:
4-Nitroacetophenone is used as a reagent in the synthesis of 4-Nitroacetophenone thiosemicarbazone derivatives and their copper(II) complexes, which have potential anti-trypanosomal activity in vitro. This application is particularly relevant in the pharmaceutical industry for developing new drugs to combat trypanosomal infections.
Used in Chemical Synthesis:
In the chemical industry, 4-Nitroacetophenone is utilized as a starting material for the synthesis of synthetic chloramphenicol, an antibiotic, through a series of reactions involving bromination and side chain buildup. It is also used in the synthesis of (R)-(4-Nitrophenyl)oxirane (N504430) and (S)-(4-Nitrophenyl)oxirane (N504435), which are important intermediates in the production of various chemicals and pharmaceuticals.
Used in Bronchodilator Production:
4-Nitroacetophenone plays a crucial role in the synthesis of the bronchodilator clenbuterol, with α-bromo-4-nitroacetophenone being the key precursor in its production. This application is significant in the pharmaceutical industry for the treatment of respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD).

Preparation

In the presence of catalyst cobalt stearate, p-nitroethylbenzene is oxidized to synthesize 4-nitroacetophenone with air at 140-150°C and 0.2MPa pressure. The reaction product is washed with water, neutralized, centrifugally dehydrated, and dried to obtain a finished product.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 4634, 1983 DOI: 10.1021/jo00172a038Synthetic Communications, 26, p. 291, 1996 DOI: 10.1080/00397919608003617

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A nitrated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Fire Hazard

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

Purification Methods

Crystallise the ketone from EtOH or aqueous EtOH. [Beilstein 7 IV 657.]

Check Digit Verification of cas no

The CAS Registry Mumber 100-19-6 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, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 100-19:
(5*1)+(4*0)+(3*0)+(2*1)+(1*9)=16
16 % 10 = 6
So 100-19-6 is a valid CAS Registry Number.
InChI:InChI:1S/C8H7NO3/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-5H,1H3

100-19-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A13877)  4'-Nitroacetophenone, 98%   

  • 100-19-6

  • 50g

  • 250.0CNY

  • Detail
  • Alfa Aesar

  • (A13877)  4'-Nitroacetophenone, 98%   

  • 100-19-6

  • 250g

  • 1042.0CNY

  • Detail
  • Alfa Aesar

  • (A13877)  4'-Nitroacetophenone, 98%   

  • 100-19-6

  • 1000g

  • 3738.0CNY

  • Detail

100-19-6SDS

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-nitroacetophenone

1.2 Other means of identification

Product number -
Other names 4'-Nitroacetophenone

1.3 Recommended use of the chemical and restrictions on use

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

1.4 Supplier's details

1.5 Emergency phone number

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

More Details:100-19-6 SDS

100-19-6Synthetic route

1-[4-nitrophenyl]-1-ethanol
6531-13-1

1-[4-nitrophenyl]-1-ethanol

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With silica-supported Jones reagent In dichloromethane for 0.00269444h;100%
With Oxone; potassium bromide In water; acetonitrile at 20℃; for 3h; Reagent/catalyst; Solvent;99%
With iodine pentoxide; potassium bromide In water at 20℃; for 12h;98%
2-methyl-2-(4-nitrophenyl)-1,3-dithiane
67395-06-6

2-methyl-2-(4-nitrophenyl)-1,3-dithiane

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With water; silver (I) ion In 1,4-dioxane at 25℃; Kinetics; Product distribution; var. temp.;100%
With dihydrogen peroxide; niobium pentachloride; sodium iodide In water; ethyl acetate at 20℃; for 5h;100%
With iron(III)-acetylacetonate; dihydrogen peroxide; sodium iodide In water; ethyl acetate at 20℃; for 18.4h;92%
tetramethylstannane
594-27-4

tetramethylstannane

4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.166667h; Mechanism;100%
With bis(η3-allyl-μ-chloropalladium(II)) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.166667h;100%
With benzoylchlorobis(triphenylphosphine)palladium(II) In chloroform at 65℃; for 24h;95%
With N,N,N,N,N,N-hexamethylphosphoric triamide; poly-γ-(diphenylphosphino)propylsiloxane palladium(0) at 65℃; for 20h;83%
1,1-dimethoxy-1-(4-nitrophenyl)ethane
53577-98-3

1,1-dimethoxy-1-(4-nitrophenyl)ethane

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With water at 80℃; for 2h;100%
With carbon tetrabromide In water; acetonitrile at 80℃; for 2h;97%
1-(4-nitrophenyl)-2-(phenylselanyl)ethan-1-one
104755-32-0

1-(4-nitrophenyl)-2-(phenylselanyl)ethan-1-one

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With GLUTATHIONE In methanol Product distribution; Mechanism; 0.1 M phosphate buffer, pH=6.9; differnt quantity of glutathione; relative reactivity to α-(phenylselenenyl)acetophenone;A 99%
B 87%
(4-Nitrophenyl)acetylene
937-31-5

(4-Nitrophenyl)acetylene

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With water at 60℃; for 20h; Sealed tube;99%
With C22H20AuN3O2P(1+)*CF3O3S(1-); water; silver trifluoromethanesulfonate; acetic acid at 100℃; for 10h;98%
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I) In methanol; water at 120℃; for 6h; Schlenk technique; regioselective reaction;94%
4-ethylnitrobenzene
100-12-9

4-ethylnitrobenzene

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry;98%
With tert.-butylhydroperoxide; phosphomolybdic acid; copper(II) acetate monohydrate In water; acetonitrile at 90℃; for 10h; Sealed tube;97%
With Oxone; water; potassium bromide In dichloromethane at 20℃; for 16h; Time; Irradiation; Sealed tube;96%
p-nitroacetophenone oxime
10342-64-0

p-nitroacetophenone oxime

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With water; oxygen In acetonitrile at 60℃; under 760.051 Torr; for 2h; Autoclave; Green chemistry;98%
With Dess-Martin periodane In dichloromethane; water for 0.25h;96%
With sodium tungstate; dihydrogen peroxide In water; acetone at -5 - 20℃; for 5h;96%
2-methyl-2-(4-nitrophenyl)-1,3-oxathiolane
131496-48-5

2-methyl-2-(4-nitrophenyl)-1,3-oxathiolane

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With t-butyl thionitrite In acetonitrile at 0℃; for 0.6h;98%
With N-Bromosuccinimide; water In acetone at 20℃; for 6h; Hydrolysis;88%
With eosin Y disodium salt In acetonitrile at 20℃; for 3h; Irradiation;68%
With oxygen; Rose Bengal lactone In ethanol pH=7.4; Kinetics;50%
1-(4-nitro-phenyl)-ethanone-diethylacetal
64600-23-3

1-(4-nitro-phenyl)-ethanone-diethylacetal

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With water at 80℃; for 2h;98%
With carbon tetrabromide In water; acetonitrile at 80℃; for 2h; Product distribution; other reaction conditions;
C17H19NO4

C17H19NO4

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With silica-OSO3H; silica gel In toluene at 60 - 70℃; for 1h;98%
With tetrachlorosilane; silica gel In toluene at 60 - 70℃; for 1.33333h;93%
With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate; aluminium trichloride In acetonitrile Heating;
4-methyl-N'-(1-(4-nitrophenyl)ethylidene)benzenesulfonohydrazide
41780-82-9

4-methyl-N'-(1-(4-nitrophenyl)ethylidene)benzenesulfonohydrazide

A

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

B

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With silica-supported selenamide; dihydrogen peroxide In tert-butyl alcohol at 55℃; for 20h;A 98%
B 2%
α,α-dibromo-4-nitroethylbenzene
90050-69-4

α,α-dibromo-4-nitroethylbenzene

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With water In dichloromethane at 20℃; for 24h; visible light irradiation;98%
2-methyl-2-(4-nitrophenyl)-1,3-dithiane
67395-06-6

2-methyl-2-(4-nitrophenyl)-1,3-dithiane

A

2,3,7,8,12,13-Hexathiatetradecane

2,3,7,8,12,13-Hexathiatetradecane

B

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With Methylthio(bismethylthio)sulfonium hexachloroantimonate In dichloromethane at -77℃; for 0.0166667h; Yields of byproduct given;A n/a
B 97%
4-Nitrophenacyl bromide
99-81-0

4-Nitrophenacyl bromide

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-d6-formamide at 20℃; for 4h; Irradiation;97%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In 2,2,2-trifluoroethanol at 20℃; for 4h; UV-irradiation; Sealed tube; Green chemistry;96%
With bismuth; ammonium fluoride-hydrogen fluoride In water at 20℃; for 3h;94%
2-(4-nitrophenyl)-2-methyl-1,3-dioxolane
19073-15-5

2-(4-nitrophenyl)-2-methyl-1,3-dioxolane

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With Montmorillonite K 10; water In acetone for 5.5h; Heating;97%
With carbon tetrabromide In water; acetonitrile at 80℃; for 6h;96%
With erbium(III) triflate In nitromethane at 20℃; for 96h;94%
1-(1-azidoethyl)-4-nitrobenzene

1-(1-azidoethyl)-4-nitrobenzene

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; vanadia In water at 100℃; for 7h;97%
3-bromo-4-(1-hydroxyethyl)nitrobenzene

3-bromo-4-(1-hydroxyethyl)nitrobenzene

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With 1-amino-3-methylbutane; ammonium chlorate; potassium bromide at 50 - 57℃; for 1h; Temperature;97%
α-(2,4-dinitrophenyl)ethyl nitrate
10061-22-0

α-(2,4-dinitrophenyl)ethyl nitrate

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With sodium ethanolate; acetic acid In ethanol at 22 - 25℃; for 0.333333h; pH=7;96%
With sodium methylate; potassium carbonate oder mit anderen Basen;
With sodium methylate; potassium carbonate oder mit anderen Basen;
1-(4-nitrophenyl)ethanone hydrazone
28153-22-2

1-(4-nitrophenyl)ethanone hydrazone

A

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

B

1-(4-nitrophenyl)-1-diazoethane
30009-48-4

1-(4-nitrophenyl)-1-diazoethane

Conditions
ConditionsYield
1-methylimidazole ligand In acetonitrile for 0.0833333h;A 4%
B 96%
4-Aminoacetophenone
99-92-3

4-Aminoacetophenone

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With water; fluorine In chloroform; acetonitrile at -15℃; for 0.0333333h; Product distribution; other substituted anilines;95%
With water; fluorine In chloroform; acetonitrile at -15℃; for 0.0333333h;95%
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h;94%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

carbon monoxide
201230-82-2

carbon monoxide

tetramethylstannane
594-27-4

tetramethylstannane

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
bis(η3-allyl-μ-chloropalladium(II)) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 30h;95%
With MCM-41-supported bidentate phosphine palladium(0) complex In N,N-dimethyl-formamide at 70℃; under 760.051 Torr; for 10h; Stille carbonylative cross-coupling;84%
4-ethylnitrobenzene
100-12-9

4-ethylnitrobenzene

A

1-[4-nitrophenyl]-1-ethanol
6531-13-1

1-[4-nitrophenyl]-1-ethanol

B

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With cerium(III) sulfate; barium bromate In water; acetonitrile for 24h; Heating; Title compound not separated from byproducts;A n/a
B 95%
With N-hydroxyphthalimide; oxygen; acetaldehyde In acetonitrile Ambient temperature;A 2 % Chromat.
B 22 % Chromat.
With oxygen under 760.051 Torr; Heating;A 16.5 %Chromat.
B 83.5 %Chromat.
1-(4-nitro-phenyl)-ethylamine
42142-15-4

1-(4-nitro-phenyl)-ethylamine

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With 4-phenylnaphthalene-1,2-dione In acetonitrile at 80℃; for 36h;95%
Multi-step reaction with 3 steps
1: N-chloro-succinimide / 0.17 h / 20 °C / Milling
2: triethylamine / 0.17 h / 20 °C / Milling
3: water; hydrogenchloride / tetrahydrofuran / 2 h / 20 °C
View Scheme
1-(4-nitrophenyl)-1-diazoethane
30009-48-4

1-(4-nitrophenyl)-1-diazoethane

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With N,N'-bis(salicylidene)ethylenediaminatocobalt(III) hydroxide; oxygen In acetonitrile94%
4-acetylphenylboronic acid
149104-90-5

4-acetylphenylboronic acid

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With N-Bromosuccinimide; [bis(trifluoroacetoxy)iodo]benzene; sodium nitrite In acetonitrile at 20℃; for 3h; regioselective reaction;94%
With bismuth (III) nitrate pentahydrate In toluene at 70 - 80℃; for 2h; Inert atmosphere;87%
With 1,3-disulfonic acid imidazolium nitrate In neat (no solvent) at 20℃; for 0.0166667h;78%
With dipotassium peroxodisulfate; bismuth (III) nitrate pentahydrate In benzene at 70℃; for 12h; Inert atmosphere;70%
1,2-bis(1-(4-nitrophenyl)ethylidene)hydrazine
58896-24-5

1,2-bis(1-(4-nitrophenyl)ethylidene)hydrazine

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile at 50℃; for 16h; Oxidation;93%
With 2-phenyl-1,2-benzoisoselenazol-3(2H)-one; dihydrogen peroxide In methanol; water at 65℃; for 72h;90%
With HOF* CH3CN In dichloromethane at 0℃; for 0.0166667h;90%
With sulfuric acid; silica gel In hexane for 1h;86%
4-nitro-(1-bromoethyl)benzene
19935-81-0

4-nitro-(1-bromoethyl)benzene

A

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

B

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With Oxone In water; acetonitrile at 20℃; for 5.5h;A 93%
B 5%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

carbon monoxide
201230-82-2

carbon monoxide

methylmercury(II) iodide
143-36-2

methylmercury(II) iodide

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
dichloro bis(acetonitrile) palladium(II) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; under 760 Torr; for 1.5h; Product distribution; various solvents, Pd-catalysts and reaction conditions;92%
With tetra-(n-butyl)ammonium iodide; dichloro bis(acetonitrile) palladium(II) In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; under 760 Torr; for 1.5h;85%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

p-nitroacetophenone oxime
10342-64-0

p-nitroacetophenone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride100%
With hydroxylamine hydrochloride; sodium acetate In ethanol for 0.0166667h; Condensation; Irradiation;98%
With hydroxylamine hydrochloride; silica gel for 0.1h;95%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

N-(4-acetylphenyl)hydroxylamine
10517-47-2

N-(4-acetylphenyl)hydroxylamine

Conditions
ConditionsYield
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; for 3.5h; Inert atmosphere;100%
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; Inert atmosphere;100%
With rhodium contaminated with carbon; hydrazine hydrate In tetrahydrofuran at 0℃; for 3.5h; Inert atmosphere;100%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

1-[4-nitrophenyl]-1-ethanol
6531-13-1

1-[4-nitrophenyl]-1-ethanol

Conditions
ConditionsYield
With methyltriphenylphosphonium tetrahydroborate In dichloromethane Reduction;100%
Stage #1: (4-nitrophenyl)ethanone With sodium tetrahydroborate at 25℃; for 0.5h; Ball milling; neat (no solvent);
Stage #2: With water regiospecific reaction;
100%
With C40H37ClN2PRuS(1+)*C24H20B(1-); isopropyl alcohol; potassium hydroxide at 82℃; for 2h; Catalytic behavior;100%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

4-Nitrophenacyl bromide
99-81-0

4-Nitrophenacyl bromide

Conditions
ConditionsYield
With bromine In 1,4-dioxane; diethyl ether for 0.5h; Ambient temperature;100%
With copper(ll) bromide In ethyl acetate at 60 - 65℃; for 8h;99%
With copper(ll) bromide In ethyl acetate at 60 - 65℃; for 8h;99%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

4-Aminoacetophenone
99-92-3

4-Aminoacetophenone

Conditions
ConditionsYield
With hydrogen In methanol at 20℃; under 760.051 Torr; for 9h;100%
With hydrogenchloride; ammonium chloride In tetrahydrofuran; water at 45℃; for 2h; Sealed tube; Green chemistry;100%
With hydrogen In water at 50℃; under 750.075 Torr; for 1.5h;100%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

trimethyl orthoformate
149-73-5

trimethyl orthoformate

1,1-dimethoxy-1-(4-nitrophenyl)ethane
53577-98-3

1,1-dimethoxy-1-(4-nitrophenyl)ethane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol for 72h;100%
With toluene-4-sulfonic acid In methanol at 20℃;95%
With toluene-4-sulfonic acid In methanol at 20℃; for 48h;58%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

3-(4-chlorophenyl)-1-(4-nitrophenyl)-2-propen-1-one
25870-65-9

3-(4-chlorophenyl)-1-(4-nitrophenyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 20℃; for 0.5h;100%
Stage #1: 4-chlorobenzaldehyde; (4-nitrophenyl)ethanone With calcium hydroxyapatite In methanol at 20℃; for 0.0833333h;
Stage #2: With water for 1h; Claisen Schmidt condensation; Microwave irradiation;
93%
With sodium hydroxide In ethanol at 20℃;85%
ethylene glycol
107-21-1

ethylene glycol

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

2-(4-nitrophenyl)-2-methyl-1,3-dioxolane
19073-15-5

2-(4-nitrophenyl)-2-methyl-1,3-dioxolane

Conditions
ConditionsYield
With zeolite HSZ-360 In toluene for 1h; Heating;100%
With cyclohexane at 105℃; for 1h; Dean-Stark;100%
With ammonium bisulphate for 6h; Concentration; Reagent/catalyst; Dean-Stark; Reflux; Green chemistry;99%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

4-nitroacetophenone oxime
59862-56-5

4-nitroacetophenone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In methanol; water Reflux;100%
With hydroxylamine hydrochloride; sodium acetate In methanol Reflux;100%
With N-hydroxyphthalimide In water at 90℃; for 10h; Sealed tube;98%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

(1R)-1-(4-nitrophenyl)ethanol
6531-13-1, 96156-72-8, 99531-06-3, 58287-18-6

(1R)-1-(4-nitrophenyl)ethanol

Conditions
ConditionsYield
With (S,S)-RuCl2(2,2'-bis(di-3,5-xylylphosphino)-1,1'-binaphthyl)(1,1-dianisyl-2-isopropyl-1,2-ethylenediamine); potassium tert-butylate; hydrogen In isopropyl alcohol at 26 - 30℃; under 6080 Torr; for 15h;100%
With N(CH2)3CHCPh2OBO(n-Oct)100%
With sodium tetrahydroborate; chloro-trimethyl-silane; polymer-supported chiral sulfonamide In tetrahydrofuran Heating;99%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With glucose dehydrogenase; D-glucose; ketoreductase from Pichia glucozyma; nicotinamide adenine dinucleotide phosphate In aq. buffer at 30℃; pH=8; Enzymatic reaction; enantioselective reaction;100%
With D-glucose at 30℃; for 72h; pH=6.5; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;99%
With D-glucose In aq. phosphate buffer at 25℃; for 24h; pH=7.0; stereoselective reaction;99%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

9-oxo-4,9-dihydro-pyrazolo[5,1-b]quinazoline-3-carbaldehyde
39998-67-9

9-oxo-4,9-dihydro-pyrazolo[5,1-b]quinazoline-3-carbaldehyde

3-[(E)-3-(4-Nitro-phenyl)-3-oxo-propenyl]-4H-pyrazolo[5,1-b]quinazolin-9-one
209746-51-0

3-[(E)-3-(4-Nitro-phenyl)-3-oxo-propenyl]-4H-pyrazolo[5,1-b]quinazolin-9-one

Conditions
ConditionsYield
With piperidine In acetic acid; benzene for 24h; Heating;100%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

2-(4-nitrophenyl)-2-(trimethylsiloxy)propanenitrile

2-(4-nitrophenyl)-2-(trimethylsiloxy)propanenitrile

Conditions
ConditionsYield
With lithium tetrafluoroborate In acetonitrile at 20℃; for 7h;100%
With potassium phtalimide at 20℃; for 1.5h; solvent-free;99%
With rasta resin-PPh3BnCl In chloroform at 50℃; for 1.5h; Inert atmosphere;99%
N-(2-bromobenzyl)-2-aminoethanol
251326-32-6

N-(2-bromobenzyl)-2-aminoethanol

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

2-(4-nitrophenyl)-2-methyl-3-(2-bromobenzyl)oxazolidine

2-(4-nitrophenyl)-2-methyl-3-(2-bromobenzyl)oxazolidine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene cyclocondensation; Heating;100%
With p-toluenesulfonic acid monohydrate In benzene for 12h; Heating;100%
tetraallyl tin
7393-43-3

tetraallyl tin

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

1-p-nitrophenyl-1-methylbut-3-en-1-ol

1-p-nitrophenyl-1-methylbut-3-en-1-ol

Conditions
ConditionsYield
2,6-dimethylpyridine; zinc trifluoromethanesulfonate In dichloromethane at 20℃; for 24h;100%
With C20H32N2O10 In water at 25℃; for 24h;97%
With gadolinium(III) chloride In acetonitrile at 20℃; for 3h;85%
aminoguanidinium sulfate

aminoguanidinium sulfate

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

(E)-N-[4-(1-{diaminomethylene}hydrazono)ethyl]-4-nitrobenzene hydrochloride
1020087-07-3

(E)-N-[4-(1-{diaminomethylene}hydrazono)ethyl]-4-nitrobenzene hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol; water for 1h; Heating / reflux;100%
formaldehyd
50-00-0

formaldehyd

4-benzylpyperidine
31252-42-3

4-benzylpyperidine

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

C34H41N3O3
1037020-24-8

C34H41N3O3

Conditions
ConditionsYield
With hydrogenchloride In ethanol Mannich reaction; Heating;100%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

2-cyano-3-(4-nitrophenyl)-2-propenoic acid ethyl ester
2017-89-2, 2286-33-1, 96238-12-9

2-cyano-3-(4-nitrophenyl)-2-propenoic acid ethyl ester

Conditions
ConditionsYield
With SBA-15-supported poly(4-methylvinylpyridinium hydroxide) composite In water Knoevenagel condensation; Reflux;100%
((1E,3E)-4-nitrobuta-1,3-dien-1-yl)benzene
4701-10-4, 28925-75-9

((1E,3E)-4-nitrobuta-1,3-dien-1-yl)benzene

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

(S,E)-3-(nitromethyl)-1-(4-nitrophenyl)-5-phenylpent-4-en-1-one
1207319-01-4

(S,E)-3-(nitromethyl)-1-(4-nitrophenyl)-5-phenylpent-4-en-1-one

Conditions
ConditionsYield
With (S)-di-tert-butyl 2-{3-[(1R,2R)-2-amino-1,2-diphenylethyl]thioureido}succinate In chloroform at 80℃; for 72h; Michael reaction; optical yield given as %ee; enantioselective reaction;100%
With 1-((1R,2R)-2-aminocyclohexyl)-3-(((1R,4aS,10ar)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)thiourea; p-Toluic acid In dichloromethane at 25℃; for 168h; Michael Addition; enantioselective reaction;80%
1-Methyl-1-phenylhydrazine
618-40-6

1-Methyl-1-phenylhydrazine

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

N-Methyl-N'-[1-(4-nitro-phenyl)-eth-(E)-ylidene]-N-phenyl-hydrazine

N-Methyl-N'-[1-(4-nitro-phenyl)-eth-(E)-ylidene]-N-phenyl-hydrazine

Conditions
ConditionsYield
In ethanol for 6h; Reflux;100%
N-methyl-N-(pyridin-2-yl)hydrazine
4231-74-7

N-methyl-N-(pyridin-2-yl)hydrazine

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

C14H14N4O2

C14H14N4O2

Conditions
ConditionsYield
In ethanol for 6h; Reflux;100%
propylene glycol
57-55-6

propylene glycol

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

C11H13NO4

C11H13NO4

Conditions
ConditionsYield
With cyclohexane at 105℃; for 1h; Dean-Stark;100%
1-bromo-1-propene
590-14-7

1-bromo-1-propene

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

2-(4-nitrophenyl)pent-3en-2-ol

2-(4-nitrophenyl)pent-3en-2-ol

Conditions
ConditionsYield
Stage #1: 1-bromo-1-propene With magnesium In tetrahydrofuran
Stage #2: (4-nitrophenyl)ethanone at 20℃; Cooling with ice;
100%
ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

2-methyl-2-(4-nitrophenyl)-1,3-dithiolane
41159-13-1

2-methyl-2-(4-nitrophenyl)-1,3-dithiolane

Conditions
ConditionsYield
With amberlyst-15 In acetonitrile for 1h;99.95%
In hexane for 1h; Reflux;99%
With 9,10-dihydro-10-methylacridine at 50℃; for 36h; Green chemistry;86%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

2-methyl-2-(4-nitrophenyl)-1,3-dithiane
67395-06-6

2-methyl-2-(4-nitrophenyl)-1,3-dithiane

Conditions
ConditionsYield
With amberlyst-15 In acetonitrile for 1h;99.95%
With sulfamic acid functionalized magnetic Fe3O4 nanoparticles In neat (no solvent) at 25℃; for 2h;94%
With magnesium hydrogen sulfate In acetonitrile at 80℃; for 10h; chemoselective reaction;93%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

2-(4-nitro-phenyl)-2-hydroxypropanenitrile
69813-77-0

2-(4-nitro-phenyl)-2-hydroxypropanenitrile

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 20℃; for 18h;99.7%
With titanium tetrachloride In dichloromethane at 20℃; for 18h;99.69%
With titanium tetrachloride 1.) CH2Cl2, 0 deg C; 2.) CH2Cl2, RT, 24 h;45%

100-19-6Related news

Hydrogenation of 4-Nitroacetophenone (cas 100-19-6) over Rh/silica07/19/2019

The hydrogenation of 4-nitroacetophenone (4-NAP) and 4-aminoacetophenone (4-AAP) was examined over rhodium/silica catalysts. The reactions were carried out using isopropanol as the solvent under a range of temperatures (303–333 K) and pressures (1–5 barg). An activation energy of 50 ± 4 kJ mo...detailed

100-19-6Relevant articles and documents

Cubic CuxZrO100-x as an efficient and selective catalyst for the oxidation of aromatics active methyl, alcohol, and amine groups

Bankar, Balasaheb D.,Advani, Jacky H.,Biradar, Ankush V.

, (2021)

The local structure of a supported active metal plays a vital role in determining the desired product's selectivity in heterogeneous catalysis. Herein, we have developed a simple protocol for the synthesis of Cu doped on cubic ZrO2 mixed metal oxide catalysts and used it for the selective oxidation of various functional groups. The catalyst was synthesized by varying the wt.% of Cu (1–20%) on ZrO2 by co-precipitation, followed by hydrothermal treatment. The X-ray diffraction pattern of the catalysts confirmed the formation of the cubic phase of ZrO2, and the growth of CuO occurred along the (1 1 1) plane. The microscopy analysis revealed the uniform distribution of Cu on the ZrO2 surface, while XPS analysis confirmed the presence of copper in the +2 oxidation state. The synthesized catalyst with 2 wt% loading of Cu on ZrO2 showed excellent liquid-phase oxidation properties and gave good to best conversion of active methyl groups, alcohols, and amines with high selectivities to corresponding ketones, aldehydes, and amides, respectively, under milder reaction conditions. Furthermore, the synthesized catalyst showed a broader substrate scope for the various substituted active methyl groups, alcohols, and amines with good conversion and selectivity.

Facile and efficient method for deprotection of 1,3-oxathiolanes with N,N′-dibromo-N,N′-1,2-ethanediylbis(p-toluenesulphonamide)

Ghorbani-Vaghei, Ramin,Khazaei, Ardeshir

, p. 1787 - 1791 (2004)

Aliphatic and aromatic 1,3-oxathiolanes are readily oxidized to aldehydes and ketones in good yields under mild conditions by N,N′-dibromo-N, N′-1,2-ethanediylbis(p-toluenesulphonamide) [BNBTS].

Oxidation of oximes to ketones with zeolite supported permanganate

Jadhav,Wadgaonkar,Joshi,Salunkhe

, p. 1989 - 1995 (1999)

A variety of aldoximes and ketoximes are oxidised to corresponding aldehydes and ketones in excellent yields by zeolite supported permanganate.

Heteropoly acid-based supported ionic liquid-phase catalyst for the selective oxidation of alcohols

Bordoloi, Ankur,Sahoo, Suman,Lefebvre,Halligudi

, p. 232 - 239 (2008)

A supported ionic liquid strategy has been applied for the immobilization of a heteropolyacid, molybdovanadophosphoric acid, onto ionic liquid-modified mesoporous silica SBA-15. The immobilized catalyst demonstrated high activity in the aerobic oxidation of primary and secondary alcohols to aldehydes and ketones, respectively. No overoxidation of the primary alcohols to carboxylic acids was observed. Secondary alcohols were chemoselectively oxidized to ketones in the presence of primary alcohol, hetero atom, and allyl groups. This catalyst could be recycled five times without obvious loss of activity.

Polyoxometalate-Incorporated Framework as a Heterogeneous Catalyst for Selective Oxidation of C-H Bonds of Alkylbenzenes

Hu, Xin,Ma, Pengtao,Niu, Jingyang,Wang, Hui,Wang, Jingping,Wang, Quanzhong,Wang, Yingyue,Xu, Baijie

, p. 7753 - 7761 (2021)

Developing new catalysts for highly efficient and selective oxidation of saturated C-H bonds is significant due to their thermodynamic strength. Via incorporation of PW12O403-, pyridine-2,5-dicarboxylic acids (pydc), and Fe(III) ions into one framework, a new polyoxometalate-based metal-organic framework, [HFe4O2(H2O)4(pydc)3PW12O40]·10.5H2O (FeW-PYDC), was successfully prepared by a hydrothermal method. Interestingly, FeW-PYDC features a three-dimensional porous structure with {Fe4O2} interconnecting with PW12O403- units. FeW-PYDC displayed excellent performance in the selective oxidation of C-H bonds of alkylbenzenes with high conversion (95.7%) and selectivity (96.6%). As an effective heterogeneous catalyst, FeW-PYDC demonstrates good reusability and structural stability.

Methylammonium chlorochromate adsorbed on alumina: A convenient and efficient reagent for cleavage of carbon-nitrogen double bonds under non- aqueous condition

Zhang, Gui-Sheng,Yang, De-Hong,Chen, Mi-Feng,Cai, Kun

, p. 607 - 611 (1998)

Methylammonium chlorochromate adsorbed on alumina is an easily prepared and stable reagent. With this reagent oximes and p-nitrophenylhydrazones are converted to their corresponding carbonyl compounds in good yields.

Organotellurium-catalyzed oxidative deoximation reactions using visible-light as the precise driving energy

Deng, Xin,Qian, Rongrong,Zhou, Hongwei,Yu, Lei

, p. 1029 - 1032 (2021)

Irradiated by visible light, the recyclable (PhTe)2-catalyzed oxidative deoximation reaction could occur under mild conditions. In comparison with the thermo reaction, the method employed reduced catalyst loading (1 mol% vs. 2.5 mol%), but afforded elevated product yields with expanded substrate scope. This work demonstrated that for the organotellurium-catalyzed reactions, visible light might be an even more precise driving energy than heating because it could break the Te–Te bond accurately to generate the active free radical catalytic intermediates without damaging the fragile substituents (e.g., heterocycles) of substrates. The use of O2 instead of explosive H2O2 as oxidant affords safer reaction conditions from the large-scale application viewpoint.

Deprotection of dithioacetals with 30% hydrogen peroxide catalyzed by tantalum(V) chloride-sodium iodide or niobium(V) chloride-sodium iodide

Kirihara, Masayuki,Noguchi, Takuya,Okajima, Nobuhiro,Naito, Sayuri,Ishizuka, Yuki,Harano, Aiko,Tsukiji, Hiroyuki,Takizawa, Ryu

, p. 1515 - 1520 (2012)

The reaction of dithioacetals with 30% hydrogen peroxide in the presence of catalytic amounts of tantalum(V) and iodide ion effectively produced carbonyl compounds in high yields. Dithioacetals also can be deprotected using the niobium(V) catalyzed oxidation of iodide ion by hydrogen peroxide under mild conditions.

An efficient selective oxidation of alcohols with iron zirconium phosphate under solvent-free conditions

Hajipour, Abdol Reza,Karimi, Hirbod,Masti, Amir

, p. 413 - 423 (2016)

Iron zirconium phosphate nanoparticles have been used as an efficient catalyst for the selective oxidation of a wide range of alcohols to their corresponding ketones or aldehydes using H2O2 as an oxidizing agent without any organic solvent or additive. The steric factors associated with the substrates had a significant influence on the reaction conditions. The results showed that this method can be applied for chemoselective oxidation of benzyl alcohols in the presence of aliphatic alcohols. The catalyst used in the current study was characterized by ICP-OES, XRD, N2 adsorption-desorption, NH3-TPD, Py-FTIR, SEM, and TEM.

A mild and versatile method for the oxidative cleavage of oximes and tosylhydrazones to carbonyl compounds

Bose, D. Subhas,Srinivas

, p. 977 - 978 (1998)

1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (IBX) was found to be an efficient and selective reagent for the mild oxidative cleavage of the C=N of oximes and tosylhydrazones to yield their corresponding carbonyl compounds rapidly at room temperature in high yields.

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