Cyanuric chloride

Cyanuric 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.

Cyanuric chloride
Names
IUPAC name
2,4,6-Trichloro-1,3,5-triazine
Other names
Trichlorotriazine
s-Triazine trichloride
Cyanuryl chloride
TCT
Identifiers
3D model (JSmol)
124246
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.287
EC Number
  • 203-614-9
RTECS number
  • XZ1400000
UNII
UN number 2670
Properties
C3Cl3N3
Molar mass 184.40 g·mol−1
Appearance White powder
Odor pungent
Density 1.32 g/cm3
Melting point 144–148 °C (291–298 °F; 417–421 K)
Boiling point 192 °C (378 °F; 465 K)
hydrolyzes
Solubility in organic solvents soluble
Structure
monoclinic
Hazards
Safety data sheet ICSC 1231
GHS pictograms
GHS Signal word Danger
H302, H314, H317, H330
P260, P261, P264, P270, P271, P272, P280, P284, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P320, P321, P330, P333+313, P363, P403+233, P405, P501
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 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
0
3
1
Flash point Non-flammable
Lethal dose or concentration (LD, LC):
485 mg/kg (rat, oral)
Related compounds
Related triazines
 Cyanuric acid
Cyanuric fluoride
Cyanuric bromide
Trichloroisocyanuric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

In 2005, approximately 200,000 tons were produced.[2]

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 + RNH3+Cl−

Other 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

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−, 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

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. Tappe, Horst; Helmling, Walter; Mischke, Peter; Rebsamen, Karl; Reiher, Uwe; Russ, Werner; Schläfer, Ludwig; Vermehren, Petra (2000). Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a22_651. ISBN 978-3527306732.
  5. K. Venkataraman & D. R. Wagle (1979). "Cyanuric chloride : a useful reagent for converting carboxylic acids into chlorides, esters, amides and peptides". Tetrahedron Lett. 20 (32): 3037–3040. doi:10.1016/S0040-4039(00)71006-9.
  6. 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
  7. John T. Gupton; Steven A. Andrews (1990). "β-Dimethylaminomethylenation: N,N-Dimethyl-N'-p-tolylformamidine". Organic Syntheses.; Collective Volume, 7, p. 197
  8. 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): 2357–2366. doi:10.1021/jo702462t. PMID 18307354.
  9. Reagent: DIPEA, amine protective group: BOC
  10. 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)
  11. De Luca, L.; Giacomelli, G.; Procheddu, A (2001). "A Mild and Efficient Alternative to the Classical Swern Oxidation". J. Org. Chem. 66 (23): 7907. doi:10.1021/jo015935s.
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