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Revision as of 13:01, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472735292 of page Cyanuric_chloride for the Chem/Drugbox validation project (updated: '').		Latest revision as of 17:52, 31 July 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,665 edits →Organic synthesis: replace patent (not RS) with ref to thiocyanuric acid, and replace white-spacey image with line eq
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 443546213		| verifiedrevid = 476997899
	| ImageFile = cyanuric chloride.png		| ImageFile = cyanuric chloride.png
	| ImageSize = 150px		| ImageSize = 140
	| ImageName = Structural formula
			| ImageAlt = Skeletal formula of cyanuric chloride
	| ImageFile1 = Cyanuric-chloride-3D-balls.png		| ImageFile1 = Cyanuric chloride 3D ball.png
	| ImageName1 = Ball-and-stick model
			| ImageSize1 = 160
⚫	| IUPACName = 2,4,6-Trichloro-1,3,5-triazine
			| ImageAlt1 = Ball-and-stick model of the cyanuric chloride molecule
⚫	| OtherNames = Trichlorotriazine<br/>s-Triazine trichloride<br/>Cyanuryl chloride
		⚫	| IUPACName = 2,4,6-Trichloro-1,3,5-triazine
⚫	| Section1 = {{Chembox Identifiers
		⚫	| OtherNames = Trichlorotriazine<br/>s-Triazine trichloride<br/>Cyanuryl chloride<br/>TCT
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| Section1 = {{Chembox Identifiers
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 7666		| ChemSpiderID = 7666
	| InChIKey = MGNCLNQXLYJVJD-UHFFFAOYAQ		| InChIKey = MGNCLNQXLYJVJD-UHFFFAOYAQ
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	| StdInChIKey = MGNCLNQXLYJVJD-UHFFFAOYSA-N		| StdInChIKey = MGNCLNQXLYJVJD-UHFFFAOYSA-N
	| CASNo = 108-77-0		| CASNo = 108-77-0
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
		⚫	| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| EINECS = 203-614-9
	| PubChem = 7954		| UNII = 5U4L4QHD6I
		⚫	| EINECS = 203-614-9
⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
			| PubChem = 7954
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 58964		| ChEBI = 58964
			| ChEMBL = 1530777
	| SMILES = Clc1nc(Cl)nc(Cl)n1		| SMILES = Clc1nc(Cl)nc(Cl)n1
	| InChI = 1/C3Cl3N3/c4-1-7-2(5)9-3(6)8-1		| InChI = 1/C3Cl3N3/c4-1-7-2(5)9-3(6)8-1
	| UNNumber = 2670		| UNNumber = 2670
	| RTECS = XZ1400000		| RTECS = XZ1400000
			| Beilstein = 124246
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
			| C=3 | Cl=3 | N=3
	| Formula = C<sub>3</sub>Cl<sub>3</sub>N<sub>3</sub>
	| MolarMass = 184.41 g/mol		| Appearance = White powder
		⚫	| Odor = pungent
	| Appearance = White powder
		⚫	| Density = 1.32 g/cm<sup>3</sup>
⚫	| Odor = pungent
			| MeltingPtC = 144-148
⚫	| Density = 1.32 g/cm<sup>3</sup>
	| MeltingPt = 154 °C		| BoilingPtC = 192
		⚫	| Solubility = hydrolyzes
	| BoilingPt = 192 °C
			| Solvent1 = THF
⚫	| Solubility = hydrolyzes
			| Solubility1 = 0.34 g/mL
⚫	| SolubleOther = soluble
			| Solvent2 = CHCl3
⚫	| Solvent = organic solvents
			| Solubility2 = 0.17 g/mL
		⚫	| SolubleOther = soluble
		⚫	| Solvent = organic solvents
	}}		}}
	| Section3 = {{Chembox Structure		| Section3 = {{Chembox Structure
	| CrystalStruct = monoclinic		| CrystalStruct = monoclinic
	}}		}}
	| Section7 = {{Chembox Hazards		| Section7 = {{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
		⚫	| NFPA-H = 3
	| EUClass = Very toxic ('''T+''')<br/>Harmful ('''Xn''')<br/>Corrosive ('''C''')
			| NFPA-F = 0
	| EUIndex = 613-009-00-5
	| NFPA-H = 3		| NFPA-R = 1
	| NFPA-F = 0		| NFPA-S = W
			| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}
⚫	| NFPA-R = 1
	| NFPA-O = W		| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|302|314|317|330}}
	| RPhrases = {{R14}}, {{R22}}, {{R26}}, {{R34}}, {{R43}}
			| PPhrases = {{P-phrases|260|261|264|270|271|272|280|284|301+312|301+330+331|302+352|303+361+353|304+340|305+351+338|310|320|321|330|333+313|363|403+233|405|501}}
	| SPhrases = {{S1/2}}, {{S26}}, {{S28}}, {{S36/37/39}}, {{S45}}, {{S46}}, {{S63}}
	| FlashPt = Non-flammable		| FlashPt = Non-flammable
	| PEL =		| PEL =
	| LD50 = 485 mg/kg (rat, oral)		| LD50 = 485 mg/kg (rat, oral)
	}}		}}
	| Section8 = {{Chembox Related		| Section8 = {{Chembox Related
	| OtherFunctn = ]<br/>]<br/>]		| OtherFunction = ]<br/>]<br/>]<br/>]
	| Function = ]s		| OtherFunction_label = ]s
	| OtherCpds =		| OtherCompounds =
	}}		}}
	}}		}}
			'''Cyanuric chloride''' is an ] with the ] (NCCl)<sub>3</sub>. This white solid is the ] derivative of ]. It is the ] of ].<ref></ref> Cyanuric chloride is the main precursor to the popular but controversial herbicide ].
			==Production==
			Cyanuric chloride is prepared in two steps from ] via the intermediacy of ], which is trimerized at elevated temperatures over a carbon catalyst:
			:HCN + Cl<sub>2</sub> → ClCN + HCl
			:]
			In 2005, approximately 200,000 tons 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>
			==Industrial uses==
			It is estimated that 70% of cyanuric chloride is used in the preparation of the triazine-class pesticides, especially ]. Such reactions rely on the easy displacement of the chloride with ]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>
			Other triazine herbicides, such as ], ] and ] are made in an analogous way.<ref name="ashford">Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, pages 2495-8</ref>
			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/> Many ] also incorporate a triazine ring. They are also manufactured by way of the chloride displacement reaction shown above.<ref name="ashford" /><ref name="TappeHelmling2000">{{cite book|last1=Tappe|first1=Horst|title=Ullmann's Encyclopedia of Industrial Chemistry|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|year=2000|doi=10.1002/14356007.a22_651|isbn=978-3527306732}}</ref>
			==Reactivity==
			The chloride centers are easily replaced. ]s give ] derivatives, for example in the synthesis of ]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 | author2 = Eric E. Simanek | name-list-style = amp | journal = ] | year = 2008 | volume = 73 | pages = 2357–2366 | doi = 10.1021/jo702462t | pmid = 18307354 | issue = 6| s2cid = 24304872 }}</ref><ref>Reagent: ], amine ]: ]</ref>
			:{{chem2|(ClCN)3 + R2NH -> (R2NCN)3 + 3 HCl }}
			It reacts with ] to give ] ({{chem2|(S\dCNH)3}}).<ref name=Atw>{{cite journal |doi=10.1021/ic0103188 |title=Chemistry of 2,4,6-Trimercapto-1,3,5-triazine (TMT): Acid Dissociation Constants and Group 2 Complexes |date=2001 |last1=Henke |first1=Kevin R. |last2=Hutchison |first2=Aaron R. |last3=Krepps |first3=Matthew K. |last4=Parkin |first4=Sean |last5=Atwood |first5=David A. |journal=Inorganic Chemistry |volume=40 |issue=17 |pages=4443–4447 |pmid=11487353 }}</ref>
			===Organic synthesis===
			Cyanuric chloride is employed as a ] in ] for the conversion of alcohols into alkyl chlorides,<ref>{{cite journal | journal = ] | volume = 35 | issue = 11 | pages = 3967-3968 | year = 1970 | doi = 10.1021/jo00836a088 | author = Stanley R. Sandler | title = Cyanuric chloride. A novel laboratory hydrochlorinating reagent for alcohols}}</ref> and carboxylic acids into acyl chlorides:<ref>{{cite journal | journal = ] | volume = 20 | issue = 32 | pages = 3037–3040 | year = 1979 | doi = 10.1016/S0040-4039(00)71006-9 | author = K. Venkataraman | author2 = D. R. Wagle | name-list-style = amp | title = Cyanuric chloride : a useful reagent for converting carboxylic acids into chlorides, esters, amides and peptides}}</ref>
			:]
			It is also used as a dehydrating agent, e.g. in the conversion of ] to ],<ref>{{cite journal | journal = ] | volume = 8 | pages = 657-658 | year = 1980 | doi = 10.1055/s-1980-29160 | author = George A. Olah | author2 = Subhash C. Narang | author3 = Alexander P. Fung | author4 = B. G. Balaram Gupta | name-list-style = amp | title = Synthetic Methods and Reactions; 82. Cyanuric Chloride, a Mild Dehydrating Agent in the Preparation of Nitriles from Amides}}</ref> and for the activation of carboxylic acids for reduction to alcohols. Heating with ] 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 | author2 = Steven A. Andrews | title = β-Dimethylaminomethylenation: ''N'',''N''-Dimethyl-''N''<nowiki>'</nowiki>-p-tolylformamidine}}</ref>
			Cyanuric chloride can also be used as an alternative to ] in the ].<ref>{{cite journal | last1 = De Luca | first1 = L. | last2 = Giacomelli | first2 = G. | last3 = Procheddu | first3 = A | year = 2001 | title =A Mild and Efficient Alternative to the Classical Swern Oxidation| journal = J. Org. Chem. | volume = 66| issue = 23| pages = 7907–7909 | doi=10.1021/jo015935s| pmid = 11701058 }}</ref>
			==See also==
			*] – structural analogue with sulfur atoms in-place of carbon
			==References==
			{{Reflist}}
			]
			]
			]