General Description
Yellow prisms or bright yellow powder.
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.
Air & Water Reactions
Insoluble in water.
Fire Hazard
Flash point data for this chemical are not available. P-NITROACETOPHENONE is probably combustible.
Chemical Properties
YELLOW CRYSTALLINE POWDER
Uses
4''-Nitroacetophenone is used as a reagent in the synthesis of 4-Nitroacetophenone thiosemicarbazone derivatives and their copper(II) complexes which have potential anti-trypanosomal activity in vitro. Also used as a reagent in the synthesis of (R)-(4-Nitrophenyl)oxirane (N504430) and (S)-(4-Nitrophenyl)oxirane (N504435).
Application
One of several alternative routes to synthetic chloroamphenicol uses 4-nitroacetophenone as starting material with a first-stage bromination to α-bromo-4-nitroacetophenone followed by buildup of the side chain. α-bromo-4-nitroacetophenone is the key precursor in the synthesis of the bronchodilator clenbuterol.
Definition
ChEBI: A member of the class of acetophenones that is acetophenone substituted at the para-position by a nitro group.
Preparation
In the presence of catalyst cobalt stearate, p-nitroethylbenzene is oxidized to synthesize 4-nitroacetophenone with air at 140-150°C and 0.2MPa pressure. The reaction product is washed with water, neutralized, centrifugally dehydrated, and dried to obtain a finished product.
Purification Methods
Crystallise the ketone from EtOH or aqueous EtOH. [Beilstein 7 IV 657.]
