Cyanuric chloride

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Cyanuric chloride
Skeletal formula of cyanuric chloride
Ball-and-stick model of the cyanuric chloride molecule
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 Edit this at Wikidata
EC Number
  • 203-614-9
RTECS number
  • XZ1400000
UNII
UN number 2670
  • InChI=1S/C3Cl3N3/c4-1-7-2(5)9-3(6)8-1 checkY
    Key: MGNCLNQXLYJVJD-UHFFFAOYSA-N checkY
  • InChI=1/C3Cl3N3/c4-1-7-2(5)9-3(6)8-1
    Key: MGNCLNQXLYJVJD-UHFFFAOYAQ
  • Clc1nc(Cl)nc(Cl)n1
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
Solubility in THF 0.34 g/mL
Solubility in CHCl3 0.17 g/mL
Structure
monoclinic
Hazards
Safety data sheet ICSC 1231
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Signal word
 Danger
H302, H314, H317, H330
P260, 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, P501
NFPA 704 (fire diamond)
3
0
1
W
Flash point Non-flammable
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 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).
checkY  (what is checkY☒N ?)
Infobox references

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.

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
Cyanurchloride Synthesis V.1.svg

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]

Synthesis of acyl chlorides with cyanuric chloride.png

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]

Cyanuric chloride based dendrimer

It is also employed the synthesis of an experimental adenosine receptor ligand.:[10]

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.[11]

See also[]

  • Thiazyl chloride trimer - structural analogue with sulfur atoms in-place of carbon

References[]

  1. ^ Cyanuric chloride at Chemicalland21.com
  2. ^ 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.
  3. ^ a b 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): 7907–7909. doi:10.1021/jo015935s. PMID 11701058.
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