| Cyanogen chloride | |
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Cyanic chloride |
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Other names
Chloroformonitrile, Chlorine cyanide, Carbononitridic chloride, CK |
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| Identifiers | |
| CAS number | 506-77-4 |
| PubChem | 10477 |
| ChemSpider | 10045 |
| EC number | 208-052-8 |
| UN number | 1589 |
| RTECS number | GT2275000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | CNCl |
| Molar mass | 61.46 g/mol |
| Appearance | colorless gas |
| Density | 1.186 g/cm3 (liquid) |
| Melting point |
−6 °C |
| Boiling point |
13 °C[1] |
| Solubility in water | Soluble |
| Vapor pressure | 1987 kPa (21.1 °C) |
| Hazards | |
| MSDS | ICSC 1053 |
| Main hazards | Highly toxic[2] |
| NFPA 704 |
0
4
2
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| Related compounds | |
| Related cyanogen halides | Cyanogen fluoride Cyanogen bromide Cyanogen iodide |
| Related compounds | Cyanogen |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Cyanogen chloride is an inorganic compound with the formula NCCl. This linear, triatomic pseudohalogen is an easily condensed colorless gas. More commonly encountered in the laboratory is the related compound cyanogen bromide, a room-temperature solid that is widely used in biochemical analysis and preparation.
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Although the formula is written CNCl, cyanogen chloride is a molecule with the connectivity ClCN. Carbon and chlorine are linked by a single bond, and carbon and nitrogen by a triple bond. It is a linear molecule, as are the related cyanogen halides (NCF, NCBr, NCI). Cyanogen chloride is produced by the oxidation of sodium cyanide with chlorine. This reaction proceeds via the intermediate cyanogen ((CN)2).[3]
The compound trimerizes in the presence of acid to the heterocycle called cyanuric chloride.
Cyanogen chloride is slowly hydrolyzed by water to release hydrogen cyanide
Cyanogen chloride is a precursor to the sulfonyl cyanides[4] and chlorosulfonyl isocyanate, a useful reagent in organic synthesis.[5]
Also known as CK, cyanogen chloride is a highly toxic blood agent, and was once proposed for use in chemical warfare. It causes immediate injury upon contact with the eyes or respiratory organs. Symptoms of exposure may include drowsiness, rhinorrhea (runny nose), sore throat, coughing, confusion, nausea, vomiting, edema, loss of consciousness, convulsions, paralysis, and death.[6] It is especially dangerous because it is capable of penetrating the filters in gas masks, according to U.S. analysts. CK is unstable due to polymerization, sometimes with explosive violence.[7]
Cyanogen chloride is listed in schedule 3 of the Chemical Weapons Convention: all production must be reported to the OPCW.
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