Hexamethylenetetramine
chemical compound
Hexamethylenetetramine (HMTA), also known as 1,3,5,7-tetraazaadamantane, is a heterocyclic organic compound with diverse applications. It has the chemical formula (CH2)6N4 and is a white crystalline compound that is highly soluble in water and polar organic solvents. It is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, explosives, and rubber additives. The compound is also used medically for certain conditions. It sublimes in vacuum at 280 °C. It has a tetrahedral cage-like structure similar to adamantane. The four vertices are occupied by nitrogen atoms, which are linked by methylene groups. Although the molecular shape defines a cage, no void space is available at the interior.
Synthesis, structure, reactivity
Hexamethylenetetramine was discovered by Aleksandr Butlerov in 1859.
It is prepared industrially by combining formaldehyde and ammonia:
The molecule behaves like an amine base, undergoing protonation and as a ligand. N-alkylation with chloroallyl chloride gives quaternium-15.
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