[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/cyanuric-chloride-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki24\/cyanuric-chloride-wikipedia\/","headline":"Cyanuric chloride – Wikipedia","name":"Cyanuric chloride – Wikipedia","description":"From Wikipedia, the free encyclopedia Cyanuric chloride Names IUPAC name 2,4,6-Trichloro-1,3,5-triazine Other names Trichlorotriazines-Triazine trichlorideCyanuryl chlorideTCT Identifiers 124246 ChEBI ChEMBL","datePublished":"2017-05-07","dateModified":"2017-05-07","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki24\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/8\/84\/Cyanuric_chloride.png\/140px-Cyanuric_chloride.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/8\/84\/Cyanuric_chloride.png\/140px-Cyanuric_chloride.png","height":"111","width":"140"},"url":"https:\/\/wiki.edu.vn\/en\/wiki24\/cyanuric-chloride-wikipedia\/","wordCount":4425,"articleBody":"From Wikipedia, the free encyclopediaCyanuric chlorideNamesIUPAC name2,4,6-Trichloro-1,3,5-triazineOther namesTrichlorotriazines-Triazine trichlorideCyanuryl chlorideTCTIdentifiers124246ChEBIChEMBLChemSpiderECHA InfoCard100.003.287 EC NumberRTECS numberUNIIUN number2670InChI=1S\/C3Cl3N3\/c4-1-7-2(5)9-3(6)8-1\u00a0YKey:\u00a0MGNCLNQXLYJVJD-UHFFFAOYSA-N\u00a0YInChI=1\/C3Cl3N3\/c4-1-7-2(5)9-3(6)8-1Key:\u00a0MGNCLNQXLYJVJD-UHFFFAOYAQPropertiesC3Cl3N3Molar mass184.40\u00a0g\u00b7mol\u22121AppearanceWhite powderOdorpungentDensity1.32 g\/cm3Melting point144\u2013148\u00a0\u00b0C (291\u2013298\u00a0\u00b0F; 417\u2013421\u00a0K)Boiling point192\u00a0\u00b0C (378\u00a0\u00b0F; 465\u00a0K)hydrolyzesSolubility in organic solventssolubleSolubility in THF0.34 g\/mLSolubility in CHCl30.17 g\/mLStructuremonoclinicHazardsGHS labelling:DangerH302, H314, H317, H330P260, P261, P264, P270, P271, P272, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P320, P321, P330, P333+P313, P363, P403+P233, P405, P501NFPA 704 (fire\u00a0diamond)Flash pointNon-flammableLethal dose or concentration (LD, LC):485 mg\/kg (rat, oral)Safety data sheet (SDS)ICSC 1231Related compoundsCyanuric acidCyanuric fluorideCyanuric bromideTrichloroisocyanuric acidExcept where otherwise noted, data are given for materials in their standard state (at 25\u00a0\u00b0C [77\u00a0\u00b0F], 100\u00a0kPa).Chemical compoundCyanuric chloride is an organic compound with the formula (NCCl)3.  This white solid is the chlorinated derivative of 1,3,5-triazine.  It is the trimer of cyanogen chloride.[1]  Cyanuric chloride is the main precursor to the popular but controversial herbicide atrazine.Table of ContentsProduction[edit]Industrial uses[edit]Organic synthesis[edit]See also[edit]References[edit]Production[edit]Cyanuric chloride is prepared in two steps from hydrogen cyanide via the intermediacy of cyanogen chloride, which is trimerized at elevated temperatures over a carbon catalyst:HCN  +  Cl2  \u2192  ClCN  +  HClIn 2005, approximately 200,000 tons were produced.[2]Industrial uses[edit]It is estimated that 70% of cyanuric chloride is used in the preparation of the triazine-class pesticides, especially atrazine.  Such reactions rely on the easy displacement of the chloride with nucleophiles such as amines:(ClCN)3  +  2 RNH2  \u2192  (RNHCN)(ClCN)2  +  RNH3+Cl\u2212Other triazine herbicides, such as simazine, anilazine and cyromazine are made in an analogous way.[3]Cyanuric chloride is also used as a precursor to dyes and crosslinking agents. The largest class of these dyes are the sulfonated triazine-stilbene optical brighteners (OBA) or fluorescent whitening agents (FWA) commonly found in detergent formulas and white paper.[2] Many reactive dyes also incorporate a triazine ring. They are also manufactured by way of the chloride displacement reaction shown above.[3][4]Organic synthesis[edit]In one specialized application, cyanuric chloride is employed as a reagent in organic synthesis for the conversion of alcohols and carboxylic acids into alkyl and acyl chlorides, respectively:[5]It is also used as a dehydrating agent and for the activation of carboxylic acids for reduction to alcohols.  Heating with DMF gives “Gold’s reagent” Me2NCH=NCH=NMe2+Cl\u2212, which is a versatile source of aminoalkylations and a precursor to heterocycles.[6][7]The chloride centers are easily replaced by amines to give melamine derivatives,  for example in the synthesis of dendrimers:[8][9]It is also employed the synthesis of an experimental adenosine receptor ligand.:[10]Cyanuric chloride can also be used as an alternative to oxalyl chloride in the Swern oxidation.[11]See also[edit]References[edit]^ Cyanuric chloride at Chemicalland21.com^ a b Klaus Huthmacher, Dieter Most “Cyanuric Acid and Cyanuric Chloride” in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002\/14356007.a08_191.^ a b Ashford’s Dictionary of Industrial Chemicals, 3rd edition, 2011, pages 2495-8^ Tappe, Horst; Helmling, Walter; Mischke, Peter; Rebsamen, Karl; Reiher, Uwe; Russ, Werner; Schl\u00e4fer, Ludwig; Vermehren, Petra (2000). Ullmann’s Encyclopedia of Industrial Chemistry. doi:10.1002\/14356007.a22_651. ISBN\u00a0978-3527306732.^ K. Venkataraman & D. R. Wagle (1979). “Cyanuric chloride\u00a0: a useful reagent for converting carboxylic acids into chlorides, esters, amides and peptides”. Tetrahedron Lett. 20 (32): 3037\u20133040. doi:10.1016\/S0040-4039(00)71006-9.^ Probst, D. A.; Hanson, P. R.; Barda, D. A. “Cyanuric Chloride” in Encyclopedia of Reagents for Organic Synthesis, 2004, John Wiley & Sons. doi:10.1002\/047084289X.rn00320^ John T. Gupton; Steven A. Andrews (1990). “\u03b2-Dimethylaminomethylenation: N,N-Dimethyl-N‘-p-tolylformamidine”. Organic Syntheses.; Collective Volume, vol.\u00a07, p.\u00a0197^ Abdellatif Chouai & Eric E. Simanek (2008). “Kilogram-Scale Synthesis of a Second-Generation Dendrimer Based on 1,3,5-Triazine Using Green and Industrially Compatible Methods with a Single Chromatographic Step”. J. Org. Chem. 73 (6): 2357\u20132366. doi:10.1021\/jo702462t. PMID\u00a018307354. S2CID\u00a024304872.^ Reagent: DIPEA, amine protective group: BOC^ WO application 03101980, “1,3,5-TRIAZINE DERIVATIVES AS LIGANDS FOR HUMAN ADENOSINE-A3 RECEPTORS”, published 2003-12-11\u00a0 (Reagent number two: norephedrine, base DIPEA)^ De Luca, L.; Giacomelli, G.; Procheddu, A (2001). “A Mild and Efficient Alternative to the Classical Swern Oxidation”. J. Org. Chem. 66 (23): 7907\u20137909. doi:10.1021\/jo015935s. PMID\u00a011701058.  "},{"@context":"http:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/cyanuric-chloride-wikipedia\/#breadcrumbitem","name":"Cyanuric chloride – Wikipedia"}}]}]