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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Carbononitridic chloride | |||
| Systematic IUPAC name Chloroformonitrile | |||
Other names
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| Identifiers | |||
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3D model (JSmol) | |||
| Abbreviations | CK | ||
| ChemSpider |
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| ECHA InfoCard | 100.007.321 | ||
| EC Number |
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| MeSH | cyanogen+chloride | ||
| RTECS number |
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| UNII | |||
| UN number | 1589 | ||
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| Properties[1] | |||
| ClCN | |||
| Molar mass | 61.470 g/mol | ||
| Appearance | Colorless gas | ||
| Odor | acrid | ||
| Density | 2.7683 mg/cm3 (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) | ||
| soluble | |||
| Solubility | soluble inethanol,ether | ||
| Vapor pressure | 1.987 MPa (at 21.1 °C) | ||
| −32.4·10−6 cm3/mol | |||
| Thermochemistry | |||
Std molar entropy(S⦵298) | 236.33 J/(mol·K) | ||
Std enthalpy of formation(ΔfH⦵298) | 137.95 kJ/mol | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | Highly toxic;[2] formscyanide in the body[3] | ||
| GHS labelling: | |||
   | |||
| Danger | |||
| NFPA 704 (fire diamond) | |||
| Flash point | nonflammable[3] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | none[3] | ||
REL (Recommended) | C 0.3 ppm (0.6 mg/m3)[3] | ||
IDLH (Immediate danger) | N.D.[3] | ||
| Safety data sheet (SDS) | inchem.org | ||
| Related compounds | |||
Related alkanenitriles | |||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Cyanogen chloride is aninorganic compound with theformulaClCN. This triatomicpseudohalogen is an easily condensed colorless gas. More commonly encountered in the laboratory is the related compoundcyanogen bromide, a room-temperature solid that is used in biochemical analysis and preparation. Cyanogen compounds are highlytoxic.
Cyanogen chloride is alinear molecule with the connectivityCl−C≡N, as areHCN and the related cyanogen halides (FCN,BrCN,ICN). The carbon and chlorine atoms are linked by asingle bond, and carbon and nitrogen by atriple bond. It is a linear molecule. Cyanogen chloride is produced by the oxidation ofsodium cyanide withchlorine. This reaction proceeds via the intermediatecyanogen ((CN)2).[4]
The compoundtrimerizes in the presence of acid to the heterocycle calledcyanuric chloride.
Cyanogen chloride is slowlyhydrolyzed by water at neutralpH to release cyanate and chloride ions:
Cyanogen chloride is a precursor to the sulfonyl cyanides[5] andchlorosulfonyl isocyanate, a useful reagent inorganic synthesis.[6]
Further chlorination gives theisocyanide dichloride.
Also known asCK, cyanogen chloride is a highly toxicblood agent, and was once proposed for use inchemical warfare. It causes immediate injury upon contact with the eyes or respiratory organs. Symptoms of exposure may includedrowsiness,rhinorrhea (runny nose),sore throat,coughing,confusion,nausea,vomiting,edema,loss of consciousness,convulsions,paralysis, and death.[2] It is especially dangerous because it is capable of penetrating the filters ingas masks, according to United States analysts. CK is unstable due topolymerization, sometimes with explosive violence.[7]
Cyanogen chloride is listed inschedule 3 of theChemical Weapons Convention: all production must be reported to theOPCW.[8]
By 1945, the U.S. Army'sChemical Warfare Service developed chemical warfare rockets intended for the new M9 and M9A1Bazookas. An M26 Gas Rocket was adapted to fire cyanogen chloride-filled warheads for these rocket launchers.[9] As it was capable of penetrating the protective filter barriers in some gas masks,[10] it was seen as an effective agent against Japanese forces (particularly those hiding in caves or bunkers) because their standard issue gas masks lacked the barriers that would provide protection against cyanogen chloride.[9][11][12] The US added the weapon to its arsenal, and considered using it, along withhydrogen cyanide, as part ofOperation Downfall, the planned invasion of Japan, but PresidentHarry Truman decided against it, instead using the atomic bombs developed by the secretManhattan Project.[13] The CK rocket was never deployed or issued to combat personnel.[9]
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