2-Aminoacetophenone

Chemical compound

Structural formula of 2-Aminoacetophenone

2-Aminoacetophenone is an organic compound with the chemical formula C₈H₉NO. It is a ketone and an amine, specifically an aromatic ketone and a primary amine. This compound is notable for its distinctive odor, which is often described as resembling that of grapes or jasmine.

Structure and Properties

2-Aminoacetophenone consists of a benzene ring substituted with an amino group (–NH₂) and an acetyl group (–COCH₃). The presence of these functional groups contributes to its chemical reactivity and physical properties. The compound is a solid at room temperature and has a characteristic odor that is detectable at low concentrations.

Synthesis

2-Aminoacetophenone can be synthesized through several methods. One common approach involves the Friedel-Crafts acylation of aniline with acetyl chloride or acetic anhydride, followed by reduction of the resulting N-acetylaniline. Another method involves the reduction of 2-nitroacetophenone, which can be prepared by the nitration of acetophenone.

Applications

2-Aminoacetophenone is used in the flavor and fragrance industry due to its pleasant aroma. It is also employed in chemical synthesis as an intermediate for the production of various pharmaceuticals and agrochemicals.

Biological Significance

In the biological context, 2-Aminoacetophenone is a metabolite produced by certain bacteria, such as Pseudomonas aeruginosa. It is associated with the characteristic odor of Pseudomonas infections and can be used as a biomarker for the presence of these bacteria.

Safety and Handling

As with many chemical compounds, appropriate safety measures should be taken when handling 2-Aminoacetophenone. It should be stored in a cool, dry place, and contact with skin and eyes should be avoided. In case of exposure, affected areas should be rinsed thoroughly with water.

Related Pages

• Acetophenone
• Aniline
• Pseudomonas aeruginosa
• Friedel-Crafts reaction