Allylamine

Allylamine is an organic compound with the formula C₃H₅NH₂. This colorless liquid is the simplest stable amine with a C=C double bond. Allylamines are a class of compounds containing this functional group. Allylamines are used as building blocks in organic synthesis and in the manufacture of pharmaceuticals, especially antifungal drugs.

Structure and properties[edit | edit source]

Allylamine consists of a vinyl group (CH₂=CH-) attached to an amino group (-NH₂). The molecule is planar. The C=C double bond and the C-N single bond are in the same plane. The molecule is polar due to the presence of the amino group.

Allylamine is a weak base. It can accept a proton to form the allylammonium ion, which has a pKa of about 9.5. The compound is also a weak nucleophile. It can react with electrophiles to form substituted allylamines.

Production[edit | edit source]

Allylamine is produced industrially by the gas-phase reaction of propylene with ammonia in the presence of a catalyst. The reaction is highly exothermic and is carried out at high temperatures.

Uses[edit | edit source]

Allylamine is used as a building block in organic synthesis. It is also used in the manufacture of pharmaceuticals, especially antifungal drugs. The allyl group can be used to introduce a variety of functional groups into a molecule, making it a versatile reagent in organic synthesis.

Health effects[edit | edit source]

Exposure to allylamine can cause irritation to the eyes, skin, and respiratory tract. It is also a potent sensitizer, meaning it can cause allergic reactions. Long-term exposure can lead to lung damage and other health problems.