Cyanuric chloride
From Wikipedia, the free encyclopedia
| Cyanuric chloride | |
|---|---|
 |
|
| IUPAC name | 2,4,6-Trichloro-1,3,5-triazine |
| Other names | Trichlorotriazine s-Triazine trichloride Cyanuryl chloride |
| Identifiers | |
| CAS number | [108-77-0] |
| EINECS number | |
| Properties | |
| Molecular formula | C3Cl3N3 |
| Molar mass | 184.41 |
| Appearance | White powder |
| Density | 1.32 g/cm3 |
| Melting point |
145-147 °C |
| Boiling point |
192 °C (decomposes) |
| Solubility in water | organic solvents |
| Solubility | hydrolyzes |
| Hazards | |
| NFPA 704 |
 0
3
1
|
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Cyanuric chloride is the chemical 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].
The compound 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=NMe2+Cl-, which is a versatile source of aminoalkylations and a precursor to heterocycles.[2]
The chlorine atoms are easily replaced by amines to a melamine for example in the the synthesis of this first generation dendrimer [3] [4]:
or in the synthesis of an experimental adenosine receptor ligand [5]:
[edit] References
- ^ Cyanuric chloride at Chemicalland21.com
- ^ 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
- ^ 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 Abdellatif Chouai and Eric E. Simanek J. Org. Chem. 2008, 73, 2357-2366 doi:10.1021/jo702462t
- ^ Reagent: DIPEA, amine protective group: BOC
- ^ WO patent application 03101980, "1,3,5-TRIAZINE DERIVATIVES AS LIGANDS FOR HUMAN ADENOSINE-A3 RECEPTORS", published 2003-12-11 (Reagent number two: norephedrine, base DIPEA)
