View source for Cyanuric chloride

{{chembox
| verifiedrevid = 268879269
| ImageFile = cyanuric chloride.png
| ImageSize = 150px
| ImageName = Structural formula
| ImageFile1 = Cyanuric-chloride-3D-balls.png
| ImageName1 = Ball-and-stick model
| IUPACName = 2,4,6-Trichloro-1,3,5-triazine
| OtherNames = Trichlorotriazine<br/>s-Triazine trichloride<br/>Cyanuryl chloride
| Section1 = {{Chembox Identifiers
|   CASNo = 108-77-0
|    CASNo_Ref = {{cascite}}
|   EINECS = 203-614-9
|   PubChem = 
|   SMILES = 
|   InChI = 
|   UNNumber = 2670
|   RTECS = XZ1400000
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>3</sub>Cl<sub>3</sub>N<sub>3</sub>
|   MolarMass = 184.41 g/mol
|   Appearance = White powder
|   Density = 1.32 g/cm<sup>3</sup>
|   MeltingPt = 154 °C
|   BoilingPt = 192 °C
|   Solubility = hydrolyzes
|   SolubleOther = soluble
|    Solvent = organic solvents
  }}
| Section7 = {{Chembox Hazards
|   ExternalMSDS = [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc12/icsc1231.htm ICSC 1231]
|   EUClass = Very toxic ('''T+''')<br/>Harmful ('''Xn''')<br/>Corrosive ('''C''')
|   EUIndex = 613-009-00-5
|   NFPA-H = 3
|   NFPA-F = 0
|   NFPA-R = 1
|   NFPA-O = W
|   RPhrases = {{R14}}, {{R22}}, {{R26}}, {{R34}}, {{R43}}
|   SPhrases = {{S1/2}}, {{S26}}, {{S28}}, {{S36/37/39}}, {{S45}}, {{S46}}, {{S63}}
|   FlashPt = Non-flammable
|   PEL = 
  }}
| Section8 = {{Chembox Related
| OtherFunctn = [[Cyanuric acid]]<br/>[[Cyanuric fluoride]]<br/>[[Trichloroisocyanuric acid]]
|    Function = [[triazine]]s
| OtherCpds = 
  }}
}}

'''Cyanuric chloride''' is the [[inorganic compound]] with the [[chemical formula|formula]] (NCCl)<sub>3</sub>.  This colorless solid is the [[organochlorine|chlorinated]] derivative of [[1,3,5-triazine]].  It is the [[trimer (chemistry)|trimer]] of [[cyanogen chloride]].<ref>[http://www.chemicalland21.com/specialtychem/perchem/CYANURIC%20CHLORIDE.htm Cyanuric chloride at Chemicalland21.com]</ref>  Cyanuric chloride is the main precursor to the popular but controversial herbicide [[atrazine]].

==Production==
Cyanuric acid 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  +  Cl<sub>2</sub>  →  ClCN  +  HCl
:3 ClCN  →  (ClCN)<sub>3</sub>
In 2005, approximately 200,000 tonnes were produced.<ref name=Ullmann>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}}.
</ref>

==Precursor to pesticides==
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 [[nucleophile]]s such as amines:
:(ClCN)<sub>3</sub>  +  2 RNH<sub>2</sub>  →  (RNHCN)(ClCN)<sub>2</sub>  +  RNH<sub>3</sub><sup>+</sup>Cl<sup>-</sup>
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.<ref name=Ullmann/>

==Organic synthesis==
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:<ref>{{cite journal | journal = [[Tet. Lett.]] | volume = 20 | issue = 32 | pages = 3037–3040 | year = 1979 | doi = 10.1016/S0040-4039(00)71006-9 | author = K. Venkataraman, and D. R. Wagle | title = Cyanuric chloride : a useful reagent for converting carboxylic acids into chlorides, esters, amides and peptides}}</ref> 
:[[Image:Synthesis of acyl chlorides with cyanuric chloride.png|450px]]

It is also used as a dehydrating agent and for the activation of carboxylic acids for reduction to alcohols.  Heating with [[Dimethylformamide|DMF]] gives "Gold's reagent" Me<sub>2</sub>NCH=NCH=NMe<sub>2</sub><sup>+</sup>Cl<sup>-</sup>, which is a versatile source of aminoalkylations and a precursor to heterocycles.<ref>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}}</ref><ref>{{OrgSynth | collvol = 7 | collvolpages = 197 | prep = cv7p0197 | year = 1990 | author = John T. Gupton; Steven A. Andrews | title = β-Dimethylaminomethylenation: ''N'',''N''-Dimethyl-''N''<nowiki>'</nowiki>-p-tolylformamidine}}</ref>

The chloride centers are easily replaced by [[amine]]s to give [[melamine]] derivatives,  for example in the synthesis of [[dendrimer]]s:<ref>{{cite journal | title = 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 | author = Abdellatif Chouai and Eric E. Simanek | journal = [[J. Org. Chem.]] | year = 2008 | volume = 73 | pages = 2357–2366 | doi = 10.1021/jo702462t | pmid = 18307354 | issue = 6}}</ref><ref>Reagent: [[DIPEA]], amine [[protective group]]: [[Tert-butyloxycarbonyl protecting group|BOC]]</ref>
:[[Image:Cyanuric chloride based dendrimer.svg|450px|Cyanuric chloride based dendrimer]]

It is also employed the synthesis of an experimental [[adenosine receptor]] ligand.<ref>{{Ref patent
 |country=WO
 |number=03101980
 |status= application
 |title=1,3,5-TRIAZINE DERIVATIVES AS LIGANDS FOR HUMAN ADENOSINE-A3 RECEPTORS
 |pubdate=2003-12-11
 |fdate=
 |pridate=
 |invent1= 
 |assign1= 
}} (Reagent number two: [[norephedrine]], base [[DIPEA]])</ref>:

:[[Image:TriazineDerivativePharma.svg|450px| Example use cyanuric chloride in pharma WO 03101980 patent]]

==References==
<references/>

[[Category:Organochlorides]]
[[Category:Triazines]]
[[Category:Dehydrating agents]]

[[de:Cyanurchlorid]]
[[fr:Chlorure cyanurique]]
[[ru:Цианурхлорид]]
[[Category:2Fix]]