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Basic Information
| CAS No.: | 99-92-3 |
|---|---|
| Name: | 4-Aminoacetophenone |
| Article Data: | 368 |
| Cas Database | |
| Molecular Structure: | |
|
|
|
| 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: |
 Xn, Xi
|
| Risk Codes: | 22-36/37/38-20/21/22 |
| Safety: | 26-36 |
| PSA: | 43.09000 |
| LogP: | 2.05260 |
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Synthetic route
Conditions
| 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% |
- 83810-18-8
4-(2-methyl-1,3-dithian-2-yl)aniline
- 99-92-3
4-Aminoacetophenone
Conditions
| 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% |
- 14235-81-5
4-Ethynylaniline
- 99-92-3
4-Aminoacetophenone
Conditions
| 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% |
- 1321455-52-0
1-(4-(tert-butyldimethylsilylamino)phenyl)ethanone
- 99-92-3
4-Aminoacetophenone
Conditions
| Conditions | Yield |
|---|---|
| With silica gel In ethanol; water at 20℃; for 2h; | 100% |
- 20062-24-2
4-azidoacetophenone
- 99-92-3
4-Aminoacetophenone
Conditions
| 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% |
- 13329-40-3
4-Iodoacetophenone
- 99-92-3
4-Aminoacetophenone
Conditions
| 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% |
- 93453-80-6, 14572-89-5
1-(4-aminophenyl)ethanol
- 99-92-3
4-Aminoacetophenone
Conditions
| 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% |
Conditions
| 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 |
Conditions
| 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% |
- 232597-42-1
tert-butyl 4-acetylphenylcarbamate
- 99-92-3
4-Aminoacetophenone
Conditions
| Conditions | Yield |
|---|---|
| With water at 100℃; for 2.5h; | 97% |
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4-Aminoacetophenone
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 ℃.
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
Hazard Codes:
Xn,XiRisk 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
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