Preparation
It can be obtained by acetylation, alkylation, hydrolysis, and neutralization of m-aminophenol.
Chemical Properties
off-white to tan or light grey crystals,
Uses
3-Acetamidophenol is the ortho-regioisomer of Acetaminophen (A161220), an over-the-counter analgesic and antipyretic agent (1,2).
Definition
ChEBI: A derivative of phenol which has an acetamido substituent located meta to the phenolic -OH group. It is a non-toxic regioisomer of paracetamol with analgesic properties, but has never been marketed as a drug.
General Description
Light gray solid.
Air & Water Reactions
Water insoluble.
Reactivity Profile
Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Nitrated phenols often explode when heated. Many of them form metal salts that tend toward detonation by rather mild shock. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Fire Hazard
Flash point data for 3-ACETAMIDOPHENOL are not available. 3-ACETAMIDOPHENOL is probably combustible.
Purification Methods
Recrystallise the phenol from water. The 3,5-dinitrobenzamide complex gives orange-yellow crystals from hot H2O and has m 212o. [Beilstein 13 H 415, 13 I 132, 13 II 213, 13 III 950, 13 IV 977.]
