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3-Aminoacetophenone

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CAS:99-03-6
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3-Aminoacetophenone Basic information
Product Name:3-Aminoacetophenone
Synonyms:M-AMINOACETOPHENONE;M-AMINOACETYLBENZENE;M-AMINOPHENYLMETHYLKETONE;LABOTEST-BB LTBB000557;3-ACETYLANILINE;3-AMINOACETOPHENONE;1-(3-aminophenyl)ethanone;3-Aminoacetophenone99%
CAS:99-03-6
MF:C8H9NO
MW:135.16
EINECS:202-722-3
Product Categories:Pyridines;Aromatic Acetophenones & Derivatives (substituted);API intermediates;FINE Chemical & INTERMEDIATES;99-03-6
Mol File:99-03-6.mol
3-Aminoacetophenone Structure
3-Aminoacetophenone Chemical Properties
Melting point 94-98 °C(lit.)
Boiling point 289-290 °C(lit.)
density 1.1031 (rough estimate)
vapor pressure 1.319Pa at 25℃
refractive index 1.5700 (estimate)
Fp 289-291°C
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka3.41±0.10(Predicted)
form Solid
color Yellow to light brown crystalline powder
Water Solubility 7.056g/L(37.5 ºC)
Merck 14,413
BRN 386009
InChI1S/C8H9NO/c1-6(10)7-3-2-4-8(9)5-7/h2-5H,9H2,1H3
InChIKeyCKQHAYFOPRIUOM-UHFFFAOYSA-N
SMILESCC(=O)c1cccc(N)c1
LogP0.83
CAS DataBase Reference99-03-6(CAS DataBase Reference)
NIST Chemistry Reference3-Aminoacetophenone(99-03-6)
EPA Substance Registry System3-Aminoacetophenone (99-03-6)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 36/37-36-26
WGK Germany 2
RTECS AM5800000
TSCA TSCA listed
HazardClass IRRITANT
HS Code 29223900
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
MSDS Information
ProviderLanguage
m-Aminoacetophenone English
SigmaAldrich English
ACROS English
ALFA English
3-Aminoacetophenone Usage And Synthesis
Chemical Properties3-Aminoacetophenone is yellow to light brown crystalline powder
Uses3'-Aminoacetophenone has potential anti-bacterial properties in addition to being used in the synthesis of selective antagonists at human A2B adenosine receptors. As well, it is used in the synthesis of HIV-1 Integrase Inhibitors.
Uses3′-Aminoacetophenone (3-Acetylaniline) was used as reagent during the asymmetric total synthesis of pactamycin. It was used as starting reagent during the synthesis of curcumin mimics with substituted sulfonyl group.
DefinitionChEBI: 3'-Aminoacetophenone is an aromatic ketone.
Synthesis Reference(s)Synthetic Communications, 26, p. 973, 1996 DOI: 10.1080/00397919608003701
General Description3′-Aminoacetophenone acts as bifunctional coupling reagent during the synthesis of pyrimidines.
Safety ProfileModerately toxic by ingestion. Mddly toxic by skin contact. A skin and eye irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of NO,. See also AROMATIC AMINES.
SynthesisAdd 2.0g of m-nitroacetophenone, 0.2g of Pt/Bi2O3 (Pt content 0.2 wt%), 10mL of anhydrous methanol into a 50mL intermittent reactor, successively replace the gas in the reactor with nitrogen and hydrogen for 3-5 times, fill with hydrogen to a pressure of 1.0MPa, and raise the temperature to 70C with constant stirring, stirring speed of 600-800rpm. If the total pressure drops to below 0.5MPa, supplement hydrogen to the initial pressure. If the total pressure dropped below 0.5 MPa, hydrogen was replenished to the initial pressure. after 4 h the total pressure did not change, stirring was stopped and the mixture was cooled to room temperature. Centrifugation of the reaction mixture, the bottom of the yellow catalyst, the supernatant is green (if the conversion of m-nitroacetophenone is incomplete, the supernatant is yellow-green, by-products have nitro partial hydrogenation products nitroso compounds). A small amount of supernatant was analyzed by gas chromatography, and the conversion rate of m-nitroacetophenone was more than 99.9%, and the selectivity of m-aminoacetophenone was more than 99.9%. After the methanol in the filtrate was removed by rotary evaporation, m-aminoacetophenone was obtained, and the separation yield was 99%.
Purification MethodsRecrystallise it from EtOH or aqueous EtOH (m 99.5o). The thiosemicarbazone has m 202-204o (from EtOH). [Beilstein 14 H 45, 14 IV 96.]
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