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Cyanuric chloride

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Cyanuric chloride
Structural formula
Ball-and-stick model
Names
IUPAC name 2,4,6-Trichloro-1,3,5-triazine
Other names Trichlorotriazine
s-Triazine trichloride
Cyanuryl chloride
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.287 Edit this at Wikidata
EC Number
  • 203-614-9
PubChem CID
RTECS number
  • XZ1400000
UN number 2670
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3Cl3N3/c4-1-7-2(5)9-3(6)8-1Key: MGNCLNQXLYJVJD-UHFFFAOYSA-N
  • InChI=1/C3Cl3N3/c4-1-7-2(5)9-3(6)8-1Key: MGNCLNQXLYJVJD-UHFFFAOYAQ
SMILES
  • Clc1nc(Cl)nc(Cl)n1
Properties
Chemical formula C3Cl3N3
Molar mass 184.41 g/mol
Appearance White powder
Odor pungent
Density 1.32 g/cm
Melting point 154 °C
Boiling point 192 °C
Solubility in water hydrolyzes
Solubility in organic solvents soluble
Structure
Crystal structure monoclinic
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
3 0 1W
Flash point Non-flammable
Lethal dose or concentration (LD, LC):
LD50 (median dose) 485 mg/kg (rat, oral)
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Cyanuric chloride is the inorganic compound with the formula (NCCl)3. This colorless solid is the chlorinated derivative of 1,3,5-triazine. It is the trimer of cyanogen chloride. Cyanuric chloride is the main precursor to the popular but controversial herbicide atrazine.

Production

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 → ClCN + HCl
3 ClCN → (ClCN)3

In 2005, approximately 200,000 tonnes were produced.

Industrial Uses

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 → (RNHCN)(ClCN)2 + RNH3Cl

Other triazine herbicides, such as simazine, anilazine and cyromazine are made in an analogous way.

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. Many reactive dyes also incorporate a triazine ring. They are also manufactured by way of the chloride displacement reaction shown above.

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:

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=NMe2Cl, which is a versatile source of aminoalkylations and a precursor to heterocycles.

The chloride centers are easily replaced by amines to give melamine derivatives, for example in the synthesis of dendrimers:

Cyanuric chloride based dendrimer

It is also employed the synthesis of an experimental adenosine receptor ligand.:

Example use cyanuric chloride in pharma WO 03101980 patent

Cyanuric Chloride can also be used as an alternative to oxalyl chloride in the Swern oxidation.

References

  1. Cyanuric chloride at Chemicalland21.com
  2. ^ 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.
  3. ^ Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, pages 2495-8
  4. K. Venkataraman, and D. R. Wagle (1979). "Cyanuric chloride : a useful reagent for converting carboxylic acids into chlorides, esters, amides and peptides". Tet. Lett. 20 (32): 3037–3040. doi:10.1016/S0040-4039(00)71006-9.
  5. 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
  6. John T. Gupton; Steven A. Andrews (1990). "β-Dimethylaminomethylenation: N,N-Dimethyl-N'-p-tolylformamidine". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 7, p. 197.
  7. Abdellatif Chouai and 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): 2357–2366. doi:10.1021/jo702462t. PMID 18307354.
  8. Reagent: DIPEA, amine protective group: BOC
  9. WO application 03101980, "1,3,5-TRIAZINE DERIVATIVES AS LIGANDS FOR HUMAN ADENOSINE-A3 RECEPTORS", published 2003-12-11  (Reagent number two: norephedrine, base DIPEA)
  10. http://pubs.acs.org/doi/abs/10.1021/jo015935s De Luca, L.; Giacomelli, G.; Procheddu, A. J. Org. Chem. 2001, 7907.
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