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99-92-3

Basic Information
CAS No.: 99-92-3
Name: Ethanone,1-(4-aminophenyl)-
Article Data: 368
Cas Database
Molecular Structure:
Molecular Structure of 99-92-3 (Ethanone,1-(4-aminophenyl)-)
Formula: C8H9NO
Molecular Weight: 135.166
Synonyms: Acetophenone,4'-amino- (8CI);Acetophenone, p-amino- (3CI);1-(4-Aminophenyl)ethanone;1-Acetyl-4-aminobenzene;4-Acetylaniline;4-Acetylphenylamine;4-Aminophenylmethyl ketone;NSC 3242;p-Acetylaniline;p-Acetylphenylamine;p-Aminoacetophenone;p-Aminoacetylbenzene;p-Aminophenylmethyl ketone;4-Aminoacetophenone;
EINECS: 202-801-2
Density: 1.096 g/cm3
Melting Point: 103-107 °C(lit.)
Boiling Point: 294.8 °C at 760 mmHg
Flash Point: 132.1 °C
Solubility: It is soluble in hot water, ethanol and ether.
Appearance: slightly yellow to brown crystalline powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38-20/21/22
Safety: 26-36
Transport Information: N/A
PSA: 43.09000
LogP: 2.05260
Synthetic route
100-19-6

(4-nitrophenyl)ethanone

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%
83810-18-8

4-(2-methyl-1,3-dithian-2-yl)aniline

99-92-3

4-Aminoacetophenone

Conditions
ConditionsYield
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%
14235-81-5

4-Ethynylaniline

99-92-3

4-Aminoacetophenone

Conditions
ConditionsYield
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%
1321455-52-0

1-(4-(tert-butyldimethylsilylamino)phenyl)ethanone

99-92-3

4-Aminoacetophenone

Conditions
ConditionsYield
With silica gel In ethanol; water at 20℃; for 2h;100%
20062-24-2

4-azidoacetophenone

99-92-3

4-Aminoacetophenone

Conditions
ConditionsYield
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%
13329-40-3

4-Iodoacetophenone

99-92-3

4-Aminoacetophenone

Conditions
ConditionsYield
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%
93453-80-6, 14572-89-5

1-(4-aminophenyl)ethanol

99-92-3

4-Aminoacetophenone

Conditions
ConditionsYield
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%
103-84-4

Acetanilid

99-92-3

4-Aminoacetophenone

Conditions
ConditionsYield
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
99-90-1

para-bromoacetophenone

99-92-3

4-Aminoacetophenone

Conditions
ConditionsYield
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%
232597-42-1

tert-butyl 4-acetylphenylcarbamate

99-92-3

4-Aminoacetophenone

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

p-Aminoacetophenone(99-92-3) exists as exists as yellow needle-like crystals with a special aromatic odor. p-Aminoacetophenone(99-92-3) is soluble in hot water, Alcohol, ether, dilute hydrochloric acid and dilute sulphuric acid, lightly soluble in benzene and cold water.
Molecular Structure:
Molecular Formula: C8H9NO.
Molecular Weight: 135.17.
Density: 1.451g/cm3.
Melting Point: 105 - 107 ℃.
Boiling Point: 293 ℃ at 760 mmHg
Flash Point: 94.3 ℃.

Uses

p-Aminoacetophenone(99-92-3) is mainly used as intermediate of antitussive drugs. p-Aminoacetophenone(99-92-3) is also used to determine Palladium and Vitamin B1.

Toxicity Data With Reference

1.   

ipr-mus LD50:381 mg/kg

   GEPHDP    General Pharmacology. 14 (1983),465. NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .
2.   

ipr-rat LD50:260 mg/kg

   JPETAB    Journal of Pharmacology and Experimental Therapeutics. 80 (1944),31.
3.   

orl-mus LD50:596 mg/kg

   GEPHDP    General Pharmacology. 14 (1983),465.
4.   

ipr-mus LD50:300 mg/kg

   NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .
5.   

orl-bwd LD50:133 mg/kg

   AECTCV    Archives of Environmental Contamination and Toxicology. 12 (1983),355.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx. See also AROMATIC AMINES.
Hazard Codes: Xn,Xi
Risk Statements: 22-36/37/38-20/21/22
22: Harmful if swallowed 
36/37/38: Irritating to eyes, respiratory system and skin 
20/21/22: Harmful by inhalation, in contact with skin and if swallowed 
Safety Statements: 26-36
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36: Wear suitable protective clothing 
WGK Germany: 3
RTECS: AM5500000
TSCA: T
HS Code: 29223900