Cyanuric chloride


Cyanuric chloride
Cyanuric chloride
Identifiers
CAS number 108-77-0 YesY
PubChem 7954
ChemSpider 7666 YesY
EC number 203-614-9
UN number 2670
ChEBI CHEBI:58964 YesY
RTECS number XZ1400000
Jmol-3D images Image 1
Properties
Molecular formula C3Cl3N3
Molar mass 184.41 g/mol
Appearance White powder
Density 1.32 g/cm3
Melting point

154 °C

Boiling point

192 °C

Solubility in water hydrolyzes
Solubility in organic solvents soluble
Hazards
MSDS ICSC 1231
EU Index 613-009-00-5
EU classification Very toxic (T+)
Harmful (Xn)
Corrosive (C)
R-phrases R14, R22, R26, R34, R43
S-phrases (S1/2), S26, S28, S36/37/39, S45, S46, S63
NFPA 704
NFPA 704.svg
0
3
1
W
Flash point Non-flammable
Related compounds
Related triazines Cyanuric acid
Cyanuric fluoride
Trichloroisocyanuric acid
 YesY chloride (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[1] Cyanuric chloride is the main precursor to the popular but controversial herbicide atrazine.

Contents

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.[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]

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:[4]

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.[5][6]

The chloride centers are easily replaced by amines to give melamine derivatives, for example in the synthesis of dendrimers:[7][8]

Cyanuric chloride based dendrimer

It is also employed the synthesis of an experimental adenosine receptor ligand.[9]:

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[10].

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. ^ 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", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv7p0197 ; Coll. Vol. 7: 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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Look at other dictionaries:

  • cyanuric chloride — cianurchloridas statusas T sritis chemija formulė C₃Cl₃N₃ atitikmenys: angl. cyanuric chloride rus. цианурхлорид ryšiai: sinonimas – 2,4,6 trichlor 1,3,5 triazinas …   Chemijos terminų aiškinamasis žodynas

  • cyanuric chloride — noun : a crystalline compound C3N3Cl3 made by polymerization of cyanogen chloride and used in organic synthesis; 2,4,6 trichloro s triazine …   Useful english dictionary

  • Cyanuric fluoride — IUPAC name 2,4,6 trifluoro 1,3,5 triazine …   Wikipedia

  • Cyanuric acid — Cyanuric acid …   Wikipedia

  • cyanuric acid — /saɪəˌnjurɪk ˈæsəd/ (say suyuh.nyoohrik asuhd) noun a heterocyclic substance, C3H3N3O3.2H20, obtained by heating urea or by the action of water on cyanuric chloride; tricyanic acid …   Australian English dictionary

  • cyanuric — |sīə|n(y)u̇rik adjective Etymology: International Scientific Vocabulary cyan + Latin urea + International Scientific Vocabulary ic more at urea : relating to derivatives of symmetrical triazine formed by polymerization of certain cyanogen… …   Useful english dictionary

  • Cyanogen chloride — Cyanogen chloride …   Wikipedia

  • cyanogen chloride — noun : a colorless very pungent poisonous low boiling liquid compound CNCl obtained by the action of chlorine on hydrocyanic acid or a cyanide and polymerizing on storage to cyanuric chloride * * * a colorless, volatile, poisonous liquid, CNCl,… …   Useful english dictionary

  • 108-77-0 — Chlorure cyanurique Chlorure cyanurique Général Nom IUPAC 2,4,6 trichloro 1,3,5 triazine Synonymes …   Wikipédia en Français

  • C3Cl3N3 — Chlorure cyanurique Chlorure cyanurique Général Nom IUPAC 2,4,6 trichloro 1,3,5 triazine Synonymes …   Wikipédia en Français