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

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

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

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

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.

See also

• Amine
• Organic synthesis
• Pharmaceutical industry