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)

Flash point:

289-291°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.41±0.10(Predicted)

color 

Yellow to light brown crystalline powder

Water Solubility 

7.056g/L(37.5 ºC)

Merck 

14,413

BRN 

386009

InChI

1S/C8H9NO/c1-6(10)7-3-2-4-8(9)5-7/h2-5H,9H2,1H3

InChIKey

CKQHAYFOPRIUOM-UHFFFAOYSA-N

SMILES

CC(=O)c1cccc(N)c1

LogP

0.83

CAS DataBase Reference

99-03-6(CAS DataBase Reference)

NIST Chemistry Reference

3-Aminoacetophenone(99-03-6)

EPA Substance Registry System

3-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 Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

MSDS

• Language:English Provider:m-Aminoacetophenone
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Aminoacetophenone Usage And Synthesis

Chemical Properties

3-Aminoacetophenone is yellow to light brown crystalline powder

Uses

3'-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.

Uses

3′-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.

Definition

ChEBI: 3'-Aminoacetophenone is an aromatic ketone.

Synthesis Reference(s)

Synthetic Communications, 26, p. 973, 1996 DOI: 10.1080/00397919608003701

General Description

3′-Aminoacetophenone acts as bifunctional coupling reagent during the synthesis of pyrimidines.

Safety Profile

Moderately 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.

Synthesis

Add 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 70??C 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 Methods

Recrystallise 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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