100-19-6

Basic information

• Product Name: 4-Nitroacetophenone
• Synonyms: Ethanone, 1-(4-nitrophenyl)-;Ethanone,1-(4-nitrophenyl)-;Methyl4-nitrophenylketone;Methyl-p-nitrophenyl ketone;methyl-p-nitrophenylketone;Methylp-nitrophenylketone;p-Acetylnitrobenzene;Paranitroacetophenone
• CAS NO: 100-19-6
• Molecular Formula: C8H7NO3
• Molecular Weight: 165.15
• EINECS: 202-827-4
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);C7 to C8;Carbonyl Compounds;Ketones;Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 100-19-6.mol
• Article Data: 552

Chemical Properties

• Melting Point: 75-78 °C(lit.)
• Boiling Point: 202 °C(lit.)
• Flash Point: 201-202°C
• Appearance: Yellow/Crystalline Powder
• Density: 1.3450 (rough estimate)
• Vapor Pressure: 0.00511mmHg at 25°C
• Refractive Index: 1.5468 (estimate)
• Storage Temp.: Store below +30°C.
• Water Solubility: Insoluble in water.
• BRN: 607777
• CAS DataBase Reference: 4-Nitroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitroacetophenone(100-19-6)
• EPA Substance Registry System: 4-Nitroacetophenone(100-19-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36-22
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: AM9627000
• Hazardous Substances Data: 100-19-6(Hazardous Substances Data)

Usage

Chemical Properties

The pure product is pale yellow crystal or needle crystal. Soluble in hot ethanol, ether and benzene, insoluble in water. 4-Nitroacetophenone is the raw material for the manufacture of synthomycin and chloramphenicol.

Uses

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. Also used as a reagent in the synthesis of (R)-(4-Nitrophenyl)oxirane (N504430) and (S)-(4-Nitrophenyl)oxirane (N504435).

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.

Application

One of several alternative routes to synthetic chloroamphenicol uses 4-nitroacetophenone as starting material with a first-stage bromination to α-bromo-4-nitroacetophenone followed by buildup of the side chain. α-bromo-4-nitroacetophenone is the key precursor in the synthesis of the bronchodilator clenbuterol.

Definition

ChEBI: 4-nitroacetophenone is a member of the class of acetophenones that is acetophenone substituted at the para-position by a nitro group. It is a C-nitro compound and a member of acetophenones.

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

General Description

P-nitroacetophenone appears as yellow prisms or bright yellow powder. (NTP, 1992)

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.]

InChI:InChI:1S/C8H7NO3/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-5H,1H3

Synthetic route

1-[4-nitrophenyl]-1-ethanol (6531-13-1) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) + 4-nitro-benzoyl chloride (122-04-3) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → diphenyl diselenide (1666-13-3) + (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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)ethanone (100-19-6)

Conditions	Yield
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-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6)

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

C17H19NO4 → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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-nitrophenyl)ethanone (100-19-6) + 4-nitro-benzoic acid (62-23-7)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
With water In dichloromethane at 20℃; for 24h; visible light irradiation;	98%

2-methyl-2-(4-nitrophenyl)-1,3-dithiane (67395-06-6) → 2,3,7,8,12,13-Hexathiatetradecane + (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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 → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
With tert.-butylhydroperoxide; vanadia In water at 100℃; for 7h;	97%

3-bromo-4-(1-hydroxyethyl)nitrobenzene → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6) + 1-(4-nitrophenyl)-1-diazoethane (30009-48-4)

Conditions	Yield
1-methylimidazole ligand In acetonitrile for 0.0833333h;	A 4% B 96%

4-Aminoacetophenone (99-92-3) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) + carbon monoxide (201230-82-2) + tetramethylstannane (594-27-4) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → 1-[4-nitrophenyl]-1-ethanol (6531-13-1) + (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
With N,N'-bis(salicylidene)ethylenediaminatocobalt(III) hydroxide; oxygen In acetonitrile	94%

4-acetylphenylboronic acid (149104-90-5) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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-nitrophenyl)ethanone (100-19-6) + 4-nitro-benzoic acid (62-23-7)

Conditions	Yield
With Oxone In water; acetonitrile at 20℃; for 5.5h;	A 93% B 5%

p-nitrobenzene iodide (636-98-6) + carbon monoxide (201230-82-2) + methylmercury(II) iodide (143-36-2) → (4-nitrophenyl)ethanone (100-19-6)

Conditions	Yield
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) → p-nitroacetophenone oxime (10342-64-0)

Conditions	Yield
With hydroxylamine hydrochloride	100%
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) → N-(4-acetylphenyl)hydroxylamine (10517-47-2)

Conditions	Yield
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) → 1-[4-nitrophenyl]-1-ethanol (6531-13-1)

Conditions	Yield
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-Nitrophenacyl bromide (99-81-0)

Conditions	Yield
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-Aminoacetophenone (99-92-3)

Conditions	Yield
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) + trimethyl orthoformate (149-73-5) → 1,1-dimethoxy-1-(4-nitrophenyl)ethane (53577-98-3)

Conditions	Yield
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-nitrophenyl)ethanone (100-19-6) → 3-(4-chlorophenyl)-1-(4-nitrophenyl)-2-propen-1-one (25870-65-9)

Conditions	Yield
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) + (4-nitrophenyl)ethanone (100-19-6) → 2-(4-nitrophenyl)-2-methyl-1,3-dioxolane (19073-15-5)

Conditions	Yield
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-nitroacetophenone oxime (59862-56-5)

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

Conditions	Yield
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) → (S)-1-[4-nitrophenyl]ethanol (6531-13-1, 58287-18-6, 99531-06-3, 96156-72-8)

Conditions	Yield
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) + 9-oxo-4,9-dihydro-pyrazolo[5,1-b]quinazoline-3-carbaldehyde (39998-67-9) → 3-[(E)-3-(4-Nitro-phenyl)-3-oxo-propenyl]-4H-pyrazolo[5,1-b]quinazolin-9-one (209746-51-0)

Conditions	Yield
With piperidine In acetic acid; benzene for 24h; Heating;	100%

trimethylsilyl cyanide (7677-24-9) + (4-nitrophenyl)ethanone (100-19-6) → 2-(4-nitrophenyl)-2-(trimethylsiloxy)propanenitrile

Conditions	Yield
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) + (4-nitrophenyl)ethanone (100-19-6) → 2-(4-nitrophenyl)-2-methyl-3-(2-bromobenzyl)oxazolidine

Conditions	Yield
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) + (4-nitrophenyl)ethanone (100-19-6) → 1-p-nitrophenyl-1-methylbut-3-en-1-ol

Conditions	Yield
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 + (4-nitrophenyl)ethanone (100-19-6) → (E)-N-[4-(1-{diaminomethylene}hydrazono)ethyl]-4-nitrobenzene hydrochloride (1020087-07-3)

Conditions	Yield
With hydrogenchloride In methanol; water for 1h; Heating / reflux;	100%

formaldehyd (50-00-0) + 4-benzylpyperidine (31252-42-3) + (4-nitrophenyl)ethanone (100-19-6) → C34H41N3O3 (1037020-24-8)

Conditions	Yield
With hydrogenchloride In ethanol Mannich reaction; Heating;	100%

4-nitrobenzaldehdye (555-16-8) + ethyl 2-cyanoacetate (105-56-6) + (4-nitrophenyl)ethanone (100-19-6) → 2-cyano-3-(4-nitrophenyl)-2-propenoic acid ethyl ester (2017-89-2, 2286-33-1, 96238-12-9)

Conditions	Yield
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) + (4-nitrophenyl)ethanone (100-19-6) → (S,E)-3-(nitromethyl)-1-(4-nitrophenyl)-5-phenylpent-4-en-1-one (1207319-01-4)

Conditions	Yield
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) + (4-nitrophenyl)ethanone (100-19-6) → N-Methyl-N'-[1-(4-nitro-phenyl)-eth-(E)-ylidene]-N-phenyl-hydrazine

Conditions	Yield
In ethanol for 6h; Reflux;	100%

N-methyl-N-(pyridin-2-yl)hydrazine (4231-74-7) + (4-nitrophenyl)ethanone (100-19-6) → C14H14N4O2

Conditions	Yield
In ethanol for 6h; Reflux;	100%

propylene glycol (57-55-6) + (4-nitrophenyl)ethanone (100-19-6) → C11H13NO4

Conditions	Yield
With cyclohexane at 105℃; for 1h; Dean-Stark;	100%

1-bromo-1-propene (590-14-7) + (4-nitrophenyl)ethanone (100-19-6) → 2-(4-nitrophenyl)pent-3en-2-ol

Conditions	Yield
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) + (4-nitrophenyl)ethanone (100-19-6) → 2-methyl-2-(4-nitrophenyl)-1,3-dithiolane (41159-13-1)

Conditions	Yield
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) + (4-nitrophenyl)ethanone (100-19-6) → 2-methyl-2-(4-nitrophenyl)-1,3-dithiane (67395-06-6)

Conditions	Yield
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) + (4-nitrophenyl)ethanone (100-19-6) → 2-(4-nitro-phenyl)-2-hydroxypropanenitrile (69813-77-0)

Conditions	Yield
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%

Upstream product

• 13586-84-0 Cobalt stearate 
• 122-04-3 4-Nitrobenzoyl chloride 
• 612-22-6 2-Ethylnitrobenzene 

Downstream Products

• 82894-98-2 4-(4-NITROPHENYL)-1,2,3-THIADIAZOLE 
• 119162-48-0 3-(4-NITRO-PHENYL)-ISOXAZOL-5-YLAMINE 
• 462-95-3 DIETHOXYMETHANE 
• 3123-13-5 N-[1-(hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide 
• 37148-27-9 CLENBUTEROL 
• 612-22-6 2-Ethylnitrobenzene 
• 69708-36-7 4-AMINO-ALPHA-TERT-BUTYLAMINE-3,5-DICHLOROACETOPHENONE 
• 4423-58-9 DL-THREO-2-ACETAMIDO-L-(4-NITROPHENYL)-L,3-PROPANEDIOL 
• 91147-75-0 A-BROMO-4-NITROACETOPHENONE HEXAMINE 
• 121180-51-6 4-(1,2,3-THIADIAZOL-4-YL)ANILINE 
• 99-92-3 4-Aminoacetophenone 
• 56-75-7 Chloramphenicol 
• 78583-83-2 5-(4-NITROPHENYL)-2H-PYRAZOL-3-YLAMINE 

Recommend Products

• 123-75-1  pyrrolidine 
• 50-00-0  formaldehyd 
• 186581-53-3  diazomethane 
• 555-16-8  4-nitrobenzaldehdye 
• 5330-73-4  1-(2-(4-nitrophenyl)-2-oxoethyl)pyridin-1-ium iodide salt 
• 110-86-1  pyridine 
• 6028-92-8  (E)-1-(4-nitrophenyl)-3-(thiophen-2-yl)prop-2-en-1-one 
• 98-03-3  thiophene-2-carbaldehyde 
• 838-57-3  ethyl 4-nitrobenzoylacetate 
• 126829-33-2  isonicotinic acid-[1-(4-nitro-phenyl)-ethylLiDenehydrazide] 
• 54-85-3  isoniazid 
• 79-46-9  2-nitropropane 
• 19935-81-0  4-nitro-(1-bromoethyl)benzene 
• 141-52-6  sodium ethanolate 

Related 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