page_title: Hexahydro-1,3,5-triazine
section_title: Preparation
hierarchical_section_title: Hexahydro-1,3,5-triazine / Preparation
context_page_description: In chemistry, hexahydro-1,3,5-triazine is a class of heterocyclic compounds with the formula (CH₂NR)₃. They are reduced derivatives of 1,3,5-triazine, which have the formula (CHN)₃, a family of aromatic heterocycles. They are often called triazacyclohexanes or TACH's.
context_section_description: The parent hexahydro-1,3,5-triazine ((CH₂NH)₃) has been detected as an intermediate in the condensation of formaldehyde and ammonia, a reaction that affords hexamethylene tetraamine. The N-substituted derivatives are more stable. These N,N',N''-trisubstituted hexahydro-1,3,5-triazines arise from the condensation of the amine and formaldehyde as illustrated by the route to 1,3,5-trimethyl-1,3,5-triazacyclohexane:
  3 CH₂O  +  3 H₂NMe   →   (CH₂NMe)₃  +  3 H₂O
  The C-substituted derivatives are obtained by reaction of aldehydes and ammonia:
  3 RCHO  +  3 NH₃   →   (RCHNH)₃  +  3 H₂O
  Known as aldehyde ammonias, these compounds characteristically crystallize with water.  1-Alkanolamines are intermediates in these condensation reactions.
  The N,N',N"-triacyltriazines are trizines with acyl groups attached to the three nitrogen centers of the ring.  These triacyltriazines arise from the reaction of hexamethylene tetraamine with acid chlorides or the condensation of amides with formaldehyde.
  Unlike the parent triazines, the hexahydro derivatives are conformationally flexible.
caption: RDX, an explosive, is a hexahydro-1,3,5-triazine.