Allylamiinien

Allylamines are a class of amines in which the nitrogen atom is attached to an allyl substituent, the allyl group being CH2=CH–CH2–. The simplest member is allylamine, with the formula CH2=CH–CH2–NH2. Depending on substitution at nitrogen, allylamines can be primary, secondary, or tertiary; N-allyl derivatives are common in organic synthesis.

Industrial production of allylamines is typically by hydrogenation of acrylonitrile to give allylamine (CH2=CH–CH2–NH2). Other routes include amination of allyl halides and various hydroamination strategies. The allyl group provides a reactive terminal double bond, while the amine group affords basicity and nucleophilicity, enabling salt formation with acids and diverse transformations.

In terms of properties, allylamines are usually colorless liquids or gases with a pungent odor, and they are miscible with water and many organic solvents. They act as bases due to the amine lone pair and form ammonium salts upon reaction with acids. The presence of both the allyl moiety and the amine functionality allows these compounds to undergo a range of reactions, including conjugate additions, polymerizations, and transformations at the allylic position. They serve as intermediates in the synthesis of polymers, agrochemicals, pharmaceuticals, and other organic compounds.

Safety: Allylamines are irritants and can be toxic; exposure may affect the eyes, skin, and respiratory system. They should be handled with appropriate engineering controls, personal protective equipment, and stored in closed containers away from oxidizers.