Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 1,3,5-Triazine: Difference between pages

{{redirect|Vedita|the river|Vedița River}}

| Watchedfields = changed

| verifiedrevid = 477204630

| Name = 1,3,5-Triazine

| ImageFileL1 = 1,3,5-Triazin - 1,3,5-triazine.svg

| ImageNameL1 = 1,3,5-Triazine

| ImageFileR1 = 1,3,5-triazine-3D-vdW.png

| ImageNameR1 = 1,3,5-Triazine

| PIN = 1,3,5-Triazine<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 147 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>

| OtherNames = ''sym''-Triazine<br />''s''-Triazine<br />Cyanidine<br />Hydrogen cyanide trimer<br />Vedita

|Section1={{Chembox Identifiers

| SMILES = n1cncnc1

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| EINECS = 206-028-1

| PubChem = 9262

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8B5F4CM81E

| RTECS = XY2957000

|Section2={{Chembox Properties

| Formula = C{{sub|3}}H{{sub|3}}N{{sub|3}}

| MolarMass = 81.08 g/mol

| Appearance = White crystalline solid

| Density =

| Solubility =

| MeltingPtC = 81 to 83

| MeltingPt_notes =

| BoilingPt =

|Section3={{Chembox Structure

| MolShape = planar

| Dipole = zero

|Section7={{Chembox Hazards

| MainHazards = Sensitive to water

| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|302|314|315|335|360}}

| PPhrases = {{P-phrases|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}}

| FlashPt =

|Section8={{Chembox Related

| OtherFunction_label = [[?]]

| OtherFunction =

| OtherCompounds =

}}

'''1,3,5-Triazine''', also called '''''s''-triazine''', is an [[organic chemical compound]] with the formula (HCN){{sub|3}}. It is a six-membered [[heterocyclic]] [[aromatic]] ring, one of several isomeric [[triazine]]s. ''S''-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.

==Preparation==

Symmetrical 1,3,5-triazines are prepared by [[trimer (chemistry)|trimerization]] of certain nitriles such as [[cyanogen chloride]] or [[cyanamide]]. Benzoguanamine (with one phenyl and 2 amino substituents) is synthesised from [[benzonitrile]] and dicyandiamide.<ref>''Benzoguanamine'' J. K. Simons and M. R. Saxton [[Organic Syntheses]] Coll. Vol. 4, p.78; Vol. 33, p.13 [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0078 Article] {{Webarchive|url=https://web.archive.org/web/20120716191545/http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0078 |date=2012-07-16 }}</ref> In the [[Pinner triazine synthesis]] (named after [[Adolf Pinner]])<ref>A. Pinner, Ber. 23, 2919 (1890)</ref> the reactants are an alkyl or aryl [[amidine]] and [[phosgene]].<ref>''Name reactions and reagents in organic synthesis'', Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro</ref><ref>{{cite journal | doi = 10.1021/ja01592a028| title = Triazines. XIV. The Extension of the Pinner Synthesis of Monohydroxy-s-triazines to the Aliphatic Series. 2,4-Dimethyl-s-triazine1-3| year = 1956| last1 = Schroeder| first1 = Hansjuergen| last2 = Grundmann| first2 = Christoph| journal = Journal of the American Chemical Society| volume = 78| issue = 11| pages = 2447–2451}}</ref> Insertion of an N-H moiety into a [[hydrazide]] by a copper [[carbenoid]], followed by treatment with [[ammonium chloride]] also gives the triazine core.<ref>{{cite journal | doi = 10.1021/ol901502u| title = A Concise Route to Pyridines from Hydrazides by Metal Carbene N−H Insertion, 1,2,4-Triazine Formation, and Diels−Alder Reaction| year = 2009| last1 = Shi| first1 = Baolu| last2 = Lewis| first2 = William| last3 = Campbell| first3 = Ian B.| last4 = Moody| first4 = Christopher J.| journal = Organic Letters| volume = 11| issue = 16| pages = 3686–3688| pmid = 19719202}}</ref>

Amine-substituted triazines called [[Guanamine]]s are prepared by the condensation of [[cyanoguanidine]] with the corresponding [[nitrile]]:<ref>{{cite journal|journal=Org. Synth. |year=1953 |volume=33 |page=13 |doi=10.15227/orgsyn.033.0013 |title=Benzoguanamine |author1=J. K. Simons |author2=M. R. Saxton}}</ref>

:(H{{sub|2}}N){{sub|2}}C=NCN + RCN → (CNH{{sub|2}}){{sub|2}}(CR)N{{sub|3}}

==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.<ref>{{cite book | doi = 10.1002/047084289X.rt158.pub2| chapter = 1,3,5-Triazine| title = Encyclopedia of Reagents for Organic Synthesis| year = 2008| last1 = Böhme| first1 = Roswitha M.| last2 = Dang| first2 = Qun| isbn = 978-0471936237}}</ref>

===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 [[herbicide]]s such as [[Simazine]] and [[atrazine]]. Chlorinated triazines are the basis of an important family of [[reactive dye]]s, which are covalently attached to cellulosic materials.<ref name=Ullmann>{{cite book | doi = 10.1002/14356007.a22_651| chapter = Reactive Dyes| title = Ullmann's Encyclopedia of Industrial Chemistry| year = 2000| last1 = Tappe| first1 = Horst| last2 = Helmling| first2 = Walter| last3 = Mischke| first3 = Peter| last4 = Rebsamen| first4 = Karl| last5 = Reiher| first5 = Uwe| last6 = Russ| first6 = Werner| last7 = Schläfer| first7 = Ludwig| last8 = Vermehren| first8 = Petra| isbn = 3527306730}}</ref>

[[Image:Reactive dyes.png|500px|center|thumb|Methods for attaching reactive dyes to fibres (Cell = cellulose; R = chromophore).]]

Triazines are also found in [[pharmaceutical]] products.<ref>{{cite journal | doi = 10.1007/s10593-009-0243-5| title = Use of the ring opening reactions of 1,3,5-triazines in organic synthesis (Review)| year = 2009| last1 = Aksenov| first1 = A. V.| last2 = Aksenova| first2 = I. V.| journal = Chemistry of Heterocyclic Compounds| volume = 45| issue = 2| pages = 130–150| s2cid = 94191027}}</ref>

==References==

{{reflist}}

{{DEFAULTSORT:Triazine, 1, 3, 5-}}

[[Category:Triazines]]