Cyanuric chloride
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| Names | |
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IUPAC name
2,4,6-Trichloro-1,3,5-triazine
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| Other names
Trichlorotriazine
s-Triazine trichloride Cyanuryl chloride TCT |
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| Identifiers | |
108-77-0 
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| 3D model (Jmol) | Interactive image |
| ChEBI |
CHEBI:58964
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| ChemSpider |
7666
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| ECHA InfoCard | 100.003.287 |
| EC Number | 203-614-9 |
| PubChem | 7954 |
| RTECS number | XZ1400000 |
| UN number | 2670 |
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| Properties | |
| C3Cl3N3 | |
| Molar mass | 184.40 g·mol−1 |
| Appearance | White powder |
| Odor | pungent |
| Density | 1.32 g/cm3 |
| Melting point | 154 °C (309 °F; 427 K) |
| Boiling point | 192 °C (378 °F; 465 K) |
| hydrolyzes | |
| Solubility in organic solvents | soluble |
| Structure | |
| monoclinic | |
| Hazards | |
| Safety data sheet | ICSC 1231 |
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EU classification (DSD)
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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 | |
| Flash point | Non-flammable |
| Lethal dose or concentration (LD, LC): | |
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LD50 (median dose)
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485 mg/kg (rat, oral) |
| Related compounds | |
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Related triazines
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Cyanuric acid Cyanuric fluoride Cyanuric bromide Trichloroisocyanuric acid |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is  ?) |
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| 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. Cyanuric chloride is the main precursor to the popular but controversial herbicide atrazine.
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:
In 2005, approximately 200,000 tons were produced.
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:
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.
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=NMe2+Cl−, which is a versatile source of aminoalkylations and a precursor to heterocycles.
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