|Preferred IUPAC name
|Systematic IUPAC name
|Jmol 3D model||Interactive image|
|Molar mass||61.470 g mol−1|
|Density||2.7683 mg mL−1 (at 0 °C, 101.325 kPa)|
|Melting point||−6.55 °C (20.21 °F; 266.60 K)|
|Boiling point||13 °C (55 °F; 286 K)|
|Solubility||soluble in ethanol, ether|
|Vapor pressure||1.987 MPa (at 21.1 °C)|
|236.33 J K−1 mol−1|
Std enthalpy of
|137.95 kJ mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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.
Synthesis, basic properties, structure
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).
- NaCN + Cl2 → ClCN + NaCl
Cyanogen chloride is slowly hydrolyzed by water to release cyanate and chloride ions
- ClCN + H2O → NCO- + Cl- + 2H+
- at neutral pH
Applications in synthesis
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. 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.
- Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, FL: CRC Press. ISBN 0-8493-0487-3.
- Coleman, G. H.; Leeper, R. W.; Schulze, C. C. (1946). "Cyanogen Chloride". Inorganic Syntheses. 2: 90–94. doi:10.1002/9780470132333.ch25.
- Vrijland, M. S. A. (1977). "Sulfonyl Cyanides: Methanesulfonyl Cyanide" (PDF). Org. Synth. 57: 88.; Coll. Vol., 6, p. 727
- Graf, R. (1966). "Chlorosulfonyl Isocyanate" (PDF). Org. Synth. 46: 23.; Coll. Vol., 5, p. 226
- Cite error: Invalid
<ref>tag; no text was provided for refs named
- FM 3-8 Chemical Reference Handbook. US Army. 1967.
- Murphy-Lavoie, H. (2011). "Cyanogen Chloride Poisoning". eMedicine. MedScape.
- "National Pollutant Inventory – Cyanide compounds fact sheet". Australian Government.
- "NIOSH Pocket Guide to Chemical Hazards". Centers for Disease Control and Prevention.