Chemical Properties
White crystal
Application
1,3,5-Triazine is a useful replacement for HCN in the Gattermann reaction for the synthesis of aromatic aldehydes. It reacts with nucleophiles, e.g. amines, which is utilized in quinazoline synthesis.
Uses
1,3,5-Triazine is a reagent in oxidation reactions, in synthesis of heterocycles. Triazine derivatives are used as herbicides, pharmaceuticals, complexation agents, peptidomimetic building blocks, and dyes.
Preparation
Symmetrical 1,3,5-triazines are prepared by trimerization of certain nitriles such as cyanogen chloride or cyanimide. Benzoguanamine (with one phenyl and 2 amino substituents) is synthesised from benzonitrile and dicyandiamide. In the Pinner triazine synthesis (named after Adolf Pinner) the reactants are an alkyl or aryl amidine and phosgene. Insertion of an N-H moiety into a hydrazide by a copper carbenoid, followed by treatment with ammonium chloride also gives the triazine core.
Amine-substituted triazines called Guanamines are prepared by the condensation of cyanoguanidine with the corresponding nitrile:
(H2N)2C=NCN + RCN → (CNH2)2(CR)N3
Definition
1,3,5-Triazine, also known as s-triazine, is a six-membered ring organic compound, which is one of the isomers of triazine.
