1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclicaromatic ring, one of several isomeric triazines. s-Triazine —the "symmetric" isomer—and its derivatives are useful in a variety of applications.
As a reagent in organic synthesis, s-triazine is used as the equivalent of hydrogen cyanide (HCN). Being a solid (vs a gas for HCN), triazine is sometimes easier to handle in the laboratory. One application is in the Gattermann reaction, used to attach the formyl group to aromatic substrates.[8]
Triazine derivatives
N- and C-substituted triazines are used industrially. The most common derivative of 1,3,5-triazine is 1,3,5-triazine-2,4,6-triamine, commonly known as melamine or cyanuramide. Another important derivative is 1,3,5-triazine-2,4,6-triol better known as cyanuric acid.
Cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) is the starting point for the manufacture of many herbicides such as Simazine and atrazine. Chlorinated triazines are the basis of an important family of reactive dyes, which are covalently attached to cellulosic materials.[9]
Methods for attaching reactive dyes to fibres (Cell = cellulose; R = chromophore).
^Name reactions and reagents in organic synthesis, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro
^Schroeder, Hansjuergen; Grundmann, Christoph (1956). "Triazines. XIV. The Extension of the Pinner Synthesis of Monohydroxy-s-triazines to the Aliphatic Series. 2,4-Dimethyl-s-triazine1-3". Journal of the American Chemical Society. 78 (11): 2447–2451. doi:10.1021/ja01592a028.
^Shi, Baolu; Lewis, William; Campbell, Ian B.; Moody, Christopher J. (2009). "A Concise Route to Pyridines from Hydrazides by Metal Carbene N−H Insertion, 1,2,4-Triazine Formation, and Diels−Alder Reaction". Organic Letters. 11 (16): 3686–3688. doi:10.1021/ol901502u. PMID19719202.
^Aksenov, A. V.; Aksenova, I. V. (2009). "Use of the ring opening reactions of 1,3,5-triazines in organic synthesis (Review)". Chemistry of Heterocyclic Compounds. 45 (2): 130–150. doi:10.1007/s10593-009-0243-5. S2CID94191027.
