99-92-3

Basic information

• Product Name: 4-Aminoacetophenone
• Synonyms: 1-(4-aminophenyl)-ethanon;1-(4-aminophenyl)ethanone[qr];4’-amino-acetophenon;4’-aminoacetophenone[qr];Acetophenone, p-amino-;Acetophenone,4’-amino-;acetophenone,4-amino-[qr];acetophenone,p-amino-[qr]
• CAS NO: 99-92-3
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16
• EINECS: 202-801-2
• Product Categories: Amines;Aromatics
• Mol File: 99-92-3.mol
• Article Data: 368

Chemical Properties

• Melting Point: 103-107 °C(lit.)
• Boiling Point: 293 °C(lit.)
• Flash Point: 292-294°C
• Appearance: Slightly yellow to brown/Crystalline Powder
• Density: 0,77 g/cm
• Vapor Pressure: 0.00158mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Refrigerator
• Solubility: 6.5g/l
• PKA: 2.17±0.10(Predicted)
• Water Solubility: It is soluble in hot water, ethanol and ether.
• Merck: 14,413
• BRN: 471493
• CAS DataBase Reference: 4-Aminoacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Aminoacetophenone(99-92-3)
• EPA Substance Registry System: 4-Aminoacetophenone(99-92-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: AM5500000
• TSCA: T
• HazardClass: IRRITANT-HARMFUL
• Hazardous Substances Data: 99-92-3(Hazardous Substances Data)

Usage

Description

4-Aminoacetophenone is in the form of yellow needle-like crystals, with a melting point of 106°C, a boiling point of 293-295°C, and 195-200°C (2kPa). Soluble in hot water, soluble in alcohol, ether, dilute hydrochloric acid and dilute sulfuric acid, it is slightly soluble in benzene and cold water. Has a special pleasant fragrance. It can be used as a pharmaceutical intermediate.

Synthesis

Through a Williamson ether synthesis method and Smiles rearrangement reaction, benzamide compounds are produced, then the 4-aminoacetophenone preparation is finished after hydrolysis.

Applications

4′-Aminoacetophenone, is used in pharmaceuticals, medicines and other organic products. It is also used as a reagent for the photometric determination of Ce. As pharmaceutical intemediate or in the determination of palladium and vitaminB1.

Applications

A novel utilization of aminophenone derivative in toxicology, for treating intoxications with cyanogenic toxic substances.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. acids, Incompatible to Acid chlorides, Acid anhydrides, Chloroformates, Strong oxidizing agents, Strong reducing agents. Stable under ordinary conditions.

Chemical Properties

slightly yellow to brown crystalline powder

Uses

A novel utilization of aminophenone derivative in toxicology, for treating intoxications with cyanogenic toxic substances.

Uses

4'-Aminoacetophenone, is used in pharmaceuticals, medicines and other organic products. It is also used as a reagent for the photometric determination of Ce. As pharmaceutical intemediate or in the determination of palladium and vitaminB1.

Uses

4-Aminoacetophenone is a novel utilization of aminophenone derivative in toxicology used for treating intoxications with cyanogenic toxic substances.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 34, p. 2013, 1986 DOI: 10.1248/cpb.34.2013Tetrahedron Letters, 27, p. 4687, 1986 DOI: 10.1016/S0040-4039(00)85038-8

General Description

4′-Aminoacetophenone, commonly known as Clenbuterol Impurity D, is a related compound of sympathomimetic amine drug clenbuterol. Clenbuterol belongs to a group of compounds referred to as β-2-agonists and is generally used in the treatment of asthma.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Safety Profile

Poison by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NO,. See also AROMATIC AMINES

Purification Methods

It is soluble in hot H2O. UV (EtOH) has max 403nm (log 4.42) [Johnson J Am Chem Soc 75 2720 1953]. [Vandenbelt Anal Chem 26 726 1954.] The 2,4-dinitrophenylhydrazone has m 266-267o (from CHCl3 or EtOH) with 403nm (log 4.42), and the max semicarbazone has m 193-194o(dec)(from MeOH). The hydrochloride has m 98o(dec)(from H2O). [Beilstein 14 IV 100.]

Toxicity evaluation

Harmful if swallowed. Causes eye, skin, and respiratory tract irritation. May cause methemoglobinemia.

Synthetic route

(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-(2-methyl-1,3-dithian-2-yl)aniline (83810-18-8) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 0.333333h; Micellar solution;	100%
With Methylthio(bismethylthio)sulfonium hexachloroantimonate In dichloromethane at -77℃; for 0.0166667h;	97%
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; dihydrogen peroxide In water; acetonitrile at 20℃; for 0.5h;	96%
With hydrogen bromide; dihydrogen peroxide In acetonitrile at 25℃; for 6h;	95%

4-Ethynylaniline (14235-81-5) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With gold(III) tribromide; water at 200℃; for 0.333333h; microwave irradiation;	100%
With 5,10,15-tris(pentafluorophenyl)corrole cobalt(III) triphenyl phosphine; sulfuric acid; water In methanol at 80℃; for 12h;	99%
With trifluorormethanesulfonic acid; water In 2,2,2-trifluoroethanol at 25 - 70℃; for 45h; Sealed tube; regioselective reaction;	89%

1-(4-(tert-butyldimethylsilylamino)phenyl)ethanone (1321455-52-0) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With silica gel In ethanol; water at 20℃; for 2h;	100%

4-azidoacetophenone (20062-24-2) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With hydrazine hydrate In ethanol at 20℃; chemoselective reaction;	99%
With hydrogen; palladium In methanol; N,N-dimethyl-formamide at 20℃; under 6080.41 Torr; for 8h; Solvent; Temperature; Pressure; Inert atmosphere;	99%
With ammonium hydroxide at 90℃; for 0.666667h;	95%

4-Iodoacetophenone (13329-40-3) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 5h; Reagent/catalyst; Time; Sealed tube; Inert atmosphere;	99%
Stage #1: 4-Iodoacetophenone With potassium phosphate; 2,2,2-trifluoroacetamide; N,N`-dimethylethylenediamine; copper(l) iodide In N,N-dimethyl-formamide at 45℃; Stage #2: With methanol In N,N-dimethyl-formamide at 45℃; Further stages.;	98%
Stage #1: 4-Iodoacetophenone With copper(l) iodide; D-glucosamine hydrochloride; potassium carbonate In water; acetone at 90℃; for 0.166667h; Stage #2: With ammonia In water; acetone at 90℃; for 28h;	96%

1-(4-aminophenyl)ethanol (93453-80-6, 14572-89-5) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With silica-supported Jones reagent In dichloromethane for 0.00269444h;	98.8%
With bromopentacarbonylmanganese(I); N-methyl-N,N-di(2-pyridylmethyl)amine; acetone; sodium t-butanolate In toluene at 90℃; for 2h; Inert atmosphere; Schlenk technique; Darkness;	98%
With N-Bromosuccinimide; β‐cyclodextrin In methanol; water; acetone at 20℃; for 10h;	95%

Acetanilid (103-84-4) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With aluminium trichloride for 0.05h; Fries rearrangement; microwave irradiation;	97%
With ytterbium trifluoromethanesulfonate; lithium perchlorate In nitromethane at 100℃; for 8h; Fries rearrangement;	44%
With acetic anhydride; zinc(II) chloride

para-bromoacetophenone (99-90-1) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With C24H32N2*ClCu; ammonia; potassium carbonate In 1-methyl-pyrrolidin-2-one; methanol at 90℃; under 5171.62 Torr; for 24h; Inert atmosphere;	97%
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 4h;	97%
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; Sealed tube;	96%

tert-butyl 4-acetylphenylcarbamate (232597-42-1) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With water at 100℃; for 2.5h;	97%

C18H29NO3Si → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃;	96%

triethylamine (121-44-8) + p-aminoiodobenzene (540-37-4) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); tetrabutylammomium bromide; water; zinc(II) oxide In dimethyl sulfoxide at 100℃; for 16h;	96%
With water; oxygen; zinc(II) oxide In acetonitrile at 20℃; Irradiation;	59%

1-(4-fluorophenyl)ethanone (403-42-9) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With dipotassium peroxodisulfate; sodium azide; water; silver carbonate In N,N-dimethyl-formamide at 120℃; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Sealed tube;	96%
With sodium azide In dimethyl sulfoxide at 125℃; for 19h;	25%

p-aminoacetophenone oxime (38063-81-9) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 0.0166667h; neat (no solvent);	95%
With sodium periodate; silica gel In solid for 0.0416667h; Irradiation;	83%
With perchloric acid; dihydrogen peroxide; potassium bromide; ammonium molybdate tetrahydrate In water at 20℃; for 2h;	80%
With sulfuric acid In 1,4-dioxane; water for 0.416667h; Reflux;	80%

4,4'-diacetylazobenzene (18179-86-7) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With aminomethyl polysterene resin formic acid salt; zinc In methanol for 0.266667h;	95%
With polystyrene-CH2-NH3(+)HCO2(-); magnesium In methanol at 20℃; for 0.3h;	94%
With aminomethylpolystyrene-supported formate; palladium on activated charcoal In methanol at 20℃; for 5h;	94%

(4-nitrophenyl)ethanone (100-19-6) → 4-Aminoacetophenone (99-92-3) + 4-aminoethylbenzene (589-16-2)

Conditions	Yield
With hydrogen In glycerol at 100℃; for 2h;	A 95% B n/a
With methanesulfonic acid; palladium, 5% on calcium carbonate, poisoned with lead; hydrogen In ethanol at 30℃; under 2585.81 Torr; for 22h; Reagent/catalyst; Sealed tube;	A 66 %Chromat. B 26 %Chromat.

(4-nitrophenyl)ethanone (100-19-6) + glycerol (56-81-5) → C11H13NO5 + 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With hydrogen at 100℃; for 2h;	A n/a B 95%

4-aminobenzaldehyde oxime (3419-18-9) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With C2H5NO2*C9H7NO*6H2O*Cl2Co; dihydrogen peroxide In methanol for 2.5h; Reflux;	94%

2,2,2-trichloroethyl (4-acetylphenyl)carbamate → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With indium; ammonium chloride In ethanol for 3h; Heating;	93%

potassium 4-acetylphenyltrifluoroborate → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With ammonium hydroxide; copper(ll) sulfate pentahydrate; sodium hydroxide In water at 25℃; for 24h;	92%

2-methyl-2-(4-N-tert-butoxycarbonylphenyl)-1,3-dithiane → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With ammonium persulfate; Montmorillonite K-10 clay for 0.0333333h; microwave irradiation;	90%

1-[4-({[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]phenylmethylene}amino)phenyl]ethanone → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 20℃;	90%

4-aminoethylbenzene (589-16-2) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry;	90%
With air; Ag/AgBr/TiO2 nanotubes In neat (no solvent) at 20℃; for 12h; Irradiation; Green chemistry;	48%
With oxygen; Mn-MgAl hydrotalcite at 135℃; under 760.051 Torr; for 5h;

para-chloroacetophenone (99-91-2) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With copper(l) iodide; ammonia; C14H16N2O4; caesium carbonate at 120℃; for 24h; Sealed tube; Inert atmosphere;	89%
With ammonium hydroxide; potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation;	88%
With ammonium sulfate; bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate at 100 - 110℃; for 12h;	85%

ammonium hydroxide (1336-21-6) + para-bromoacetophenone (99-90-1) → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With copper(l) iodide In water at 200℃; for 2h; Autoclave;	89%
With copper(ll) sulfate pentahydrate; potassium phosphate tribasic heptahydrate; water; Sucrose In water at 90℃; for 15h; Catalytic behavior; Green chemistry;	75%

4-azidoacetophenone (20062-24-2) → 1-(4-aminophenyl)ethanol (93453-80-6, 14572-89-5) + 4-Aminoacetophenone (99-92-3) + 4-aminoethylbenzene (589-16-2)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h;	A 5% B 89% C 6%

4-acetylphenylsilver → 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With dipotassium peroxodisulfate; sodium azide; water; silver carbonate In N,N-dimethyl-formamide at 120℃; for 20h; Darkness; Sealed tube;	89%

(4-nitrophenyl)ethanone (100-19-6) → 4-Aminoacetophenone (99-92-3) + acetaldehyde (75-07-0) + H2

Conditions	Yield
With ethanol; titanium(IV) oxide for 0.25h; Irradiation;	A 88% B n/a C n/a

indole (120-72-9) + 2-phenyl-1,2,3,4-tetrahydroisoquinoline (3340-78-1) + (4-nitrophenyl)ethanone (100-19-6) → 1-(1H-indol-3-yl)-2-phenyl-1, 2, 3, 4-tetrahydroisoquinoline + 4-Aminoacetophenone (99-92-3)

Conditions	Yield
With Co(dmgH)2Cl2; Eosin Y In water; acetonitrile at 20℃; for 48h; Inert atmosphere; Irradiation; Sealed tube;	A 87% B 90 %Spectr.

acetic anhydride (108-24-7) + 4-Aminoacetophenone (99-92-3) → 4-(N-acetylamino)acetophenone (2719-21-3)

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere;	100%
In toluene at 20℃;	96%
In 1,4-dioxane; water at 0 - 25℃; for 2.5h; Acetylation;	95%

4-Aminoacetophenone (99-92-3) + methanesulfonyl chloride (124-63-0) → 4'-(methylsulfonylamino)acetophenone (5317-89-5)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 23h; Inert atmosphere;	100%
With pyridine In dichloromethane at 0 - 20℃; for 16h;	98%
In dichloromethane at 20 - 25℃; for 1h; Large scale;	96%

4-Aminoacetophenone (99-92-3) + p-toluenesulfonyl chloride (98-59-9) → 4-(p-toluenesulfonylamino)acetophenone (5317-94-2)

Conditions	Yield
With triethylamine In dichloromethane at 4℃;	100%
In pyridine for 1h; Ambient temperature;	96.6%
With pyridine In dichloromethane at 20℃; for 3h;	96%

4-Aminoacetophenone (99-92-3) → 1-(4-amino-3-bromophenyl)-ethanone (56759-32-1)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 20℃; for 20h; Cooling with ice;	100%
With hydrogen bromide In water; dimethyl sulfoxide at 85℃; for 4h;	99%
With N-Bromosuccinimide at 20℃; for 0.0833333h; regioselective reaction;	97%

4-Aminoacetophenone (99-92-3) → (R)-1-(4-aminophenyl)ethanol

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 4h;	100%
With N(CH2)3CHCPh2OBO(n-Oct)	100%
With potassium tert-butylate; hydrogen In isopropyl alcohol; tert-butyl alcohol at 20℃; under 1875.19 - 3375.34 Torr; for 2.5h; enantioselective reaction;	88%

4-Aminoacetophenone (99-92-3) + ethylhydrazine carboxylate (4114-31-2) → N'-[1-(4-amino-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester (540757-28-6)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 2h; Reflux; Inert atmosphere;	100%

6-bromo-3,4-methylenedioxybenzaldehyde (15930-53-7) + 4-Aminoacetophenone (99-92-3) → E-1-(4-((6-bromobenzo[d ][1,3]dioxol-5-yl)methyleneamino)-phenyl)ethanone (1206531-50-1)

Conditions	Yield
In methanol	100%

4-Aminoacetophenone (99-92-3) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → C19H15NO2

Conditions	Yield
With triethylamine In ethanol for 1h; Milling;	100%

4-Aminoacetophenone (99-92-3) + 2,5-dimethyl-piperazine (2815-34-1, 1119702-25-8) → C22H26N6O2

Conditions	Yield
Stage #1: p-aminobenzophenone With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: 2,5-dimethyl-piperazine In water for 0.5h;	100%

4-Aminoacetophenone (99-92-3) + 1-(benzenesulphonyl)-4-hydroxypyrrolidine-2-carboxylic acid (16257-76-4) → N-(4-acetylphenyl)-1-(benzenesulfonyl)-4-hydroxypyrrolidine-2-carboxamide

Conditions	Yield
With boric acid In toluene for 10h; Dean-Stark; Reflux;	100%

4-hydroxy-1-(4-nitrophenylsulphonyl)pyrrolidine-2-carboxylic acid + 4-Aminoacetophenone (99-92-3) → N-(4-acetylphenyl)-4-hydroxy-1-(4-nitrobenzenesulfonyl)pyrrolidine-2-carboxamide

Conditions	Yield
With boric acid In toluene for 10h; Dean-Stark; Reflux;	100%

carbon monoxide (201230-82-2) + o-iodo-methyl-benzoic acid (610-97-9) + 4-Aminoacetophenone (99-92-3) → 2-(4-acetylphenyl)-1H-isoindole-1,3(2H)-dione (40101-59-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 1h; Schlenk technique;	100%

4-Aminoacetophenone (99-92-3) + 1-(4-nitrophenylsulphonyl)pyrrolidine-2-carboxylic acid (88867-96-3) → N-(4-acetylphenyl)-1-(4-nitrobenzenesulfonyl)pyrrolidine-2-carboxamide

Conditions	Yield
With boric acid In toluene for 10h; Dean-Stark; Reflux;	99.98%

{benzoyl[(4-methylphenyl)sulfonyl]amino}acetic acid + 4-Aminoacetophenone (99-92-3) → N-(4-acetylphenyl)-2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]acetamide

Conditions	Yield
With boric acid In toluene for 10h; Dean-Stark; Reflux;	99.98%

N-benzenesulfonyl-L-proline (88425-46-1) + 4-Aminoacetophenone (99-92-3) → N-(4-acetylphenyl)-1-(benzenesulfonyl)pyrrolidine-2-carboxamide

Conditions	Yield
With boric acid In toluene for 10h; Dean-Stark; Reflux;	99.97%

3-(1H-indol-2-yl)-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]propanoic acid + 4-Aminoacetophenone (99-92-3) → N-(4-acetylphenyl)-3-(1H-indol-2-yl)-2-[N-(4-nitrobenzenesulfonyl)-1-phenyl formamido]propanamide

Conditions	Yield
With boric acid In toluene for 10h; Dean-Stark; Reflux;	99.97%

2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]acetic acid + 4-Aminoacetophenone (99-92-3) → N-(4-acetylphenyl)-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]acetamide

Conditions	Yield
With boric acid In toluene for 10h; Dean-Stark; Reflux;	99.58%

3-methyl-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]butanoic acid + 4-Aminoacetophenone (99-92-3) → N-(4-acetylphenyl)-3-methyl-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]butanamide

Conditions	Yield
With boric acid In toluene for 10h; Dean-Stark; Reflux;	99.58%

N--trans-4-hydroxy-L-proline (20275-18-7) + 4-Aminoacetophenone (99-92-3) → N-(4-acetylphenyl)-4-hydroxy-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxamide

Conditions	Yield
With boric acid In toluene for 10h; Dean-Stark; Reflux;	99.48%

indole-2,3-dione (91-56-5) + 4-Aminoacetophenone (99-92-3) → 2-(4'-aminophenyl)-4-quinolinecarboxylic acid (94205-62-6)

Conditions	Yield
With water; potassium hydroxide In ethanol at 100℃;	99%
With potassium hydroxide In ethanol Heating;	86%
With potassium hydroxide In ethanol; water Pfitzinger reaction; Heating;	85.9%
Stage #1: indole-2,3-dione With cetyltrimethylammonium hydroxide In water at 20℃; for 0.166667h; Pfitzinger Quinoline Synthesis; Sonication; Green chemistry; Stage #2: p-aminobenzophenone In water at 35℃; for 4.5h; Temperature; Pfitzinger Quinoline Synthesis; Sonication; Green chemistry;	75%
With potassium hydroxide

chloroformic acid ethyl ester (541-41-3) + 4-Aminoacetophenone (99-92-3) → ethyl (4-acetylphenyl)carbamate (5520-79-6)

Conditions	Yield
With pyridine In acetone for 3h; Reflux;	99%

4-Aminoacetophenone (99-92-3) + methyl chloroformate (79-22-1) → methyl N-(4-acetylphenyl)carbamate (60677-43-2)

Conditions	Yield
With pyridine In acetone for 3h; Reflux;	99%
With sodium hydroxide In 1,4-dioxane; water at 0 - 25℃; for 2.5h; alkoxycarbonylation;	98%
With pyridine at 20℃; for 15h; Cooling;	91%

4-Aminoacetophenone (99-92-3) → para-chloroacetophenone (99-91-2)

Conditions	Yield
Stage #1: p-aminobenzophenone With tert.-butylnitrite In acetonitrile at 20℃; Sandmeyer Reaction; Flow reactor; Stage #2: With copper dichloride In ethylene glycol; acetonitrile at 82℃; Sandmeyer Reaction; Flow reactor;	99%
With N-chloro-succinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 6h;	77%
With tert.-butylnitrite; copper dichloride In acetonitrile
With hydrogenchloride; potassium nitrite; dimethyl sulfoxide; copper(l) chloride In water at 35℃; for 0.333333h;	82 % Chromat.

4-Aminoacetophenone (99-92-3) + trifluoroacetic anhydride (407-25-0) → N-(4-acetylphenyl)-2,2,2-trifluoroacetamide (24568-13-6)

Conditions	Yield
With triethylamine In dichloromethane at 10℃;	99%
With triethylamine at 20℃; for 12h;	80%
In N,N-dimethyl-formamide for 48h; Ambient temperature;	73%

4-Aminoacetophenone (99-92-3) → 4-azidoacetophenone (20062-24-2)

Conditions	Yield
Stage #1: p-aminobenzophenone With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: With sodium azide In water at 5℃;	99%
With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 20℃; for 2h;	95%
Stage #1: p-aminobenzophenone With hydrogenchloride In water at 0 - 5℃; for 0.166667h; Stage #2: With 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy]ethyl)-1H-imidazol-3-ium dinitrite In water for 0.166667h; Stage #3: With sodium azide In water at 20℃; for 0.166667h; Ionic liquid;	95%

4-Aminoacetophenone (99-92-3) + 3-phenylnorbornadiene-2-carbonyl chloride (158198-05-1) → 3-Phenyl-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid (4-acetyl-phenyl)-amide

Conditions	Yield
With triethylamine In 1,4-dioxane for 0.166667h; Heating;	99%

Upstream product

• 100-19-6 4-Nitroacetophenone 
• 103-84-4 Acetanilide 
• 959-66-0 2-BENZOYLACETANILIDE 
• 10025-69-1 Stannous chloride dihydrate 
• 64-17-5 Etanol 
• 62-53-3 Aniline 
• 7646-85-7 Zinc chloride 

Downstream Products

• 10041-06-2 4'-(IMIDAZOL-1-YL)ACETOPHENONE 
• 37148-48-4 4-Amino-3,5-dichloroacetophenone 
• 13329-40-3 4'-Iodoacetophenone 
• 21889-05-4 4-(1H-INDOL-2-YL)-PHENYLAMINE 
• 69708-36-7 4-AMINO-ALPHA-TERT-BUTYLAMINE-3,5-DICHLOROACETOPHENONE 
• 99-93-4 4'-Hydroxyacetophenone 
• 3441-14-3 Direct Red 23 
• 968-81-0 ACETOHEXAMIDE 

Recommend Products

• 1197-55-3  4-aminophenylacetic acid 
• 110-91-8  morpholine 
• 5325-89-3  (E)-1-(4′-aminophenyl)-3-(pyridin-2-yl)prop-2-en-1-one 
• 1121-60-4  pyridine-2-carbaldehyde 
• 116595-35-8  2-{[(4-acetylphenyl)amino]methyl}-1H-isoindole-1,3(2H)-dione 
• 136918-14-4  phthalimide 
• 50-00-0  formaldehyd 
• 3397-62-4  2-Chloro-4,6-diamino-1,3,5-triazine 
• 10440-43-4  1-(4-(7-chloroquinolin-4-ylamino)phenyl)ethanone 
• 86-98-6  4,7-dichloroquinoline 
• 607-43-2  6-iodo-2-(4-iodo-phenyl)-quinoline-4-carboxylic acid 
• 20780-76-1  5-iodoisatin 
• 5520-79-6  ethyl (4-acetylphenyl)carbamate 
• 541-41-3  chloroformic acid ethyl ester