Cyanogen chloride: Difference between revisions
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'''Cyanogen chloride''' is |
'''Cyanogen chloride''' is an [[organic compound]] with the [[chemical formula|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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==Synthesis, basic properties, structure== |
==Synthesis, basic properties, structure== |
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Revision as of 23:36, 8 March 2017
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Carbononitridic chloride | |||
| Systematic IUPAC name
Chloroformonitrile | |||
Other names
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| Identifiers | |||
3D model (JSmol)
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| Abbreviations | CK | ||
| ChemSpider | |||
| ECHA InfoCard | 100.007.321 | ||
| EC Number |
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| MeSH | cyanogen+chloride | ||
PubChem CID
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| RTECS number |
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| UN number | 1589 | ||
CompTox Dashboard (EPA)
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| Properties[1] | |||
| CNCl | |||
| Molar mass | 61.470 g mol−1 | ||
| Appearance | Colorless gas | ||
| Odor | acrid | ||
| 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) | ||
| soluble | |||
| Solubility | soluble in ethanol, 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 K−1 mol−1 | ||
Std enthalpy of
formation (ΔfH⦵298) |
137.95 kJ mol−1 | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
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Highly toxic;[2] forms cyanide in the body[3] | ||
| NFPA 704 (fire diamond) | |||
| Flash point | nonflammable [3] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible)
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none[3] | ||
REL (Recommended)
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C 0.3 ppm (0.6 mg/m3)[3] | ||
IDLH (Immediate danger)
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N.D.[3] | ||
| Safety data sheet (SDS) | inchem.org | ||
| Related compounds | |||
Related alkanenitriles
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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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Cyanogen chloride is an organic 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).[4]
- NaCN + Cl2 → ClCN + NaCl
The compound trimerizes in the presence of acid to the heterocycle called cyanuric chloride.
Cyanogen chloride is slowly hydrolyzed by water to release cyanate and chloride ions
- ClCN + H2O → NCO− + Cl− + 2H+
- at neutral pH
Applications in synthesis
Cyanogen chloride is a precursor to the sulfonyl cyanides[5] and chlorosulfonyl isocyanate, a useful reagent in organic synthesis.[6]
Safety
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.[2] 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.[citation needed]
References
- ^ Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, FL: CRC Press. ISBN 0-8493-0487-3.
- ^ a b "CYANOGEN CHLORIDE (CK)". The Emergency Response Safety and Health Database. NIOSH.
- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0162". National Institute for Occupational Safety and Health (NIOSH).
- ^ 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). Organic Syntheses. 57: 88; Collected Volumes, vol. 6, p. 727.
- ^ Graf, R. (1966). "Chlorosulfonyl Isocyanate" (PDF). Organic Syntheses. 46: 23; Collected Volumes, vol. 5, p. 226.
- ^ FM 3-8 Chemical Reference Handbook. US Army. 1967.
External links
- 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.