3-Nitroacetophenone

Chemical Properties

white to light beige crystalline powder or yellow needle-like crystals. soluble in hot water and ether, slightly soluble in ethanol. can be volatile with water vapor.

Uses

3′-Nitroacetophenone can undergo high hydrostatic pressure-assisted reduction with Ni–Al alloy in water to form 1-(3-aminophenyl)ethanol.

Uses

3''-Nitroacetophenone is used as a reactant in the synthesis of fluorine based aminothiazoles with antimicrobial activity.

Preparation

3-Nitroacetophenone is synthesized from acetophenone by nitration.
Synthesis of 3-nitroacetophenone

Production Methods

Acetophenone is carefully dissolved in concentrated sulfuric acid at 0 ℃, and mixed acid is added slowly below 0 ℃. The crude product is precipitated by quenching into ice, filtered, and washed acid free. Purification, mainly from the ortho isomer, is achieved by recrystallization from ethanol with significant lowering of the overall yield to ca. 55 %.

General Description

3-nitroacetophenone is a light beige powder. It is an anthropogenic compound which is used as a synthetic intermediate in the production of dyes and other organic compounds. (NTP, 1992)

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A nitrated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Fire Hazard

Flash point data for 3-Nitroacetophenone are not available, however 3-Nitroacetophenone is probably combustible.

Purification Methods

Distil the ketone in steam and crystallise it from EtOH. [Beilstein 7 IV 656.]