1,3,5-Triazine

Vedita the river Vedița River changed 477204630 1,3,5-Triazine 1,3,5-Triazin - 1,3,5-triazine.svg 1,3,5-Triazine 1,3,5-triazine-3D-vdW.png 1,3,5-Triazine 1,3,5-Triazine Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) The Royal Society of Chemistry 2014 Cambridge 147 10.1039/9781849733069-FP001 978-0-85404-182-4 sym-Triazines-TriazineCyanidineHydrogen cyanide trimerVedita n1cncnc1 correct chemspider correct EBI 30259 8905 1/C3H3N3/c1-4-2-6-3-5-1/h1-3H JIHQDMXYYFUGFV-UHFFFAOYAG correct EBI 15698 206-028-1 9262 correct chemspider 1S/C3H3N3/c1-4-2-6-3-5-1/h1-3H correct chemspider JIHQDMXYYFUGFV-UHFFFAOYSA-N correct CAS 290-87-9 correct FDA 8B5F4CM81E XY2957000 C3H3N3 81.08 g/mol White crystalline solid 81 to 83 planar zero Sensitive to water 05 07 08 Danger 302 314 315 335 360 201 202 260 261 264 270 271 280 281 301+312 301+330+331 302+352 303+361+353 304+340 305+351+338 308+313 310 312 321 330 332+313 362 363 403+233 405 501 ? 1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. s-Triazine —the "symmetric" isomer—and its derivatives are useful in a variety of applications. Preparation Symmetrical 1,3,5-triazines are prepared by trimerization of certain nitriles such as cyanogen chloride or cyanamide. Benzoguanamine (with one phenyl and 2 amino substituents) is synthesised from benzonitrile and dicyandiamide.Benzoguanamine J. K. Simons and M. R. Saxton Organic Syntheses Coll. Vol. 4, p.78; Vol. 33, p.13 Article https://web.archive.org/web/20120716191545/http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0078 2012-07-16 In the Pinner triazine synthesis (named after Adolf Pinner)A. Pinner, Ber. 23, 2919 (1890) the reactants are an alkyl or aryl amidine and phosgene.Name reactions and reagents in organic synthesis, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro 10.1021/ja01592a028 Triazines. XIV. The Extension of the Pinner Synthesis of Monohydroxy-s-triazines to the Aliphatic Series. 2,4-Dimethyl-s-triazine1-3 1956 Schroeder Hansjuergen Grundmann Christoph Journal of the American Chemical Society 78 11 2447–2451 Insertion of an N-H moiety into a hydrazide by a copper carbenoid, followed by treatment with ammonium chloride also gives the triazine core. 10.1021/ol901502u A Concise Route to Pyridines from Hydrazides by Metal Carbene N−H Insertion, 1,2,4-Triazine Formation, and Diels−Alder Reaction 2009 Shi Baolu Lewis William Campbell Ian B. Moody Christopher J. Organic Letters 11 16 3686–3688 19719202 Amine-substituted triazines called Guanamines are prepared by the condensation of cyanoguanidine with the corresponding nitrile:Org. Synth. 1953 33 13 10.15227/orgsyn.033.0013 free Benzoguanamine J. K. Simons M. R. Saxton (H2N)2C=NCN + RCN → (CNH2)2(CR)N3 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. 10.1002/047084289X.rt158.pub2 1,3,5-Triazine Encyclopedia of Reagents for Organic Synthesis 2008 Böhme Roswitha M. Dang Qun 978-0471936237 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. 10.1002/14356007.a22_651 Reactive Dyes Ullmann's Encyclopedia of Industrial Chemistry 2000 Tappe Horst Helmling Walter Mischke Peter Rebsamen Karl Reiher Uwe Russ Werner Schläfer Ludwig Vermehren Petra 3527306730 500px|center|thumb|Methods for attaching reactive dyes to fibres (Cell = cellulose; R = chromophore). Triazines are also found in pharmaceutical products. 10.1007/s10593-009-0243-5 Use of the ring opening reactions of 1,3,5-triazines in organic synthesis (Review) 2009 Aksenov A. V. Aksenova I. V. Chemistry of Heterocyclic Compounds 45 2 130–150 94191027 References Category:Triazines Category:Trimers (chemistry)