Chemical Properties
It is a solid at room temperature,
with a melting point of 58°C and a boiling point of
173.4°C (at 8mmHg). Butyl p-aminobenzoate is insoluble
in water.
Uses
n-Butyl 4-aminobenzoate is used as pharmaceutical intermediate.
Definition
ChEBI: An amino acid ester resulting from the formal condensation of the carboxy group of 4-aminobenzoic acid with the hydroxy group of butan-1-ol. Its local anaesthetic properties have been used for surface anaesthesia of the skin and mucous membranes, and for r
lief of pain and itching associated with some anorectal disorders.
Production Methods
Butyl p-aminobenzoate is manufactured via esterification of
p-nitrobenzoic acid with n-butyl alcohol, followed by the
reduction of the nitro group to an amino group.
brand name
Butesin
(Abbott).
General Description
Yellow powder. Insoluble in water.
Air & Water Reactions
May be sensitive to light and air. Insoluble in water. Slowly hydrolyzed when boiled in water. Also will hydrolyze under high and low pH conditions .
Reactivity Profile
Butyl 4-aminobenzoate is an aminophenyl ester derivative. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Fire Hazard
Flash point data for Butyl 4-aminobenzoate are not available. Butyl 4-aminobenzoate is probably combustible.
Purification Methods
Crystallise Butamben from EtOH. [Beilstein 14 IV 1130.]
