What Is Allylamine?
Allylamine is an organic compound with the chemical formula C3H7N and the specific formula CH2=CHCH2NH2.
Its IUPAC nomenclature names are prop-2-ene-1-amine and 3-amino-1-propene; other names include 3-aminopropene, 3-aminopropylene, monoallylamine, 2-propenamine, 2-propen-1-amine, etc. Its CAS registration number is 107-11-9.
It has a molecular weight of 57.09, a melting point of -126.4°F (-88°C), and a boiling point of 131°F (55°C). It is a clear colorless to pale yellow liquid at room temperature. It has a density of 0.76 g/mL and a strong, pungent odor. It is extremely soluble in water, ethanol, and acetone.
It has an extremely low flash point of -18.4°F (-28°C). It is also a highly flammable liquid or vapor.
Uses of Allylamine
Allylamine is used as a raw material for agricultural chemicals, a modifier of polymer compounds, and a pharmaceutical intermediate. Some of its derivatives are also used as allylamine antifungal agents.
For example, terbinafine (trade name Lamisil) is an antifungal agent indicated for the treatment of dermatophytes and dermatomycoses caused by Candida, Sporothrix, and other fungi. One of its derivatives, diallylamine, is used as an important intermediate in industrial synthesis.
Properties of Allylamine
The 2-propenyl group (-CH2CH=CH2) in allylamine is called the allyl group, and the carbon position adjacent to the double bond is called the allyl position. The allyl group is distinct from the aryl group, which denotes an aromatic group, having a different structure.
The allyl group is used as a protecting group for alcohols and amines and is deprotected by palladium catalysts. In allylamine, the allyl group can also be removed by using palladium.
Carbocation, carbo-anion, and radical at the allyl position are stabilized by resonance. Therefore, allylamine tends to polymerize, forming homopolymers (polyallylamine) or copolymers. These polymers are used in reverse osmosis membranes.
Types of Allylamine
Allylamines sold as products are mainly reagent products for research and development and industrial chemicals. Reagent products are available in capacities of 25 ml, 50 ml, 500 ml, 5 g, 25 g, etc. These reagent products can be handled at room temperature.
Related compounds, such as allylamine hydrochloride and poly(allylamine) solution, are also available as reagent products. Various derivatives such as diallylamine and N-allylmethylamine are also sold as reagent products for organic synthesis in many compounds.
Other Information on Allylamine
1. Synthesis of Allylamine
Mixtures of allylamine (monoallylamine), diallylamine, and triallylamine are obtained by treating allyl chloride with aqueous ammonia or hexamine. Pure allylamine can also be synthesized by hydrolysis of allyl isothiocyanate.
2. Chemical Reaction of Allylamine
Allylamine reacts with nitrous acid to give allyl alcohol. It can also be methylated with methyl iodide to form N-allylmethylamine. Reaction with bromine in an acidic solution leads to an addition reaction to alkenes, yielding 2,3-dibromopropylamine.
3. Regulatory Information on Allylamine
Allylamine is designated as a toxic substance. Handling in compliance with laws and regulations is required.