| Revision as of 16:15, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 469304575 of page Cyanogen_chloride for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 13:43, 30 October 2024 edit Mondtaler (talk | contribs)182 edits GHS04 specifically addresses hazards linked to the pressurized storage of gases. As storage methods can vary, that pictogram is not universally applicable to all gaseous compounds.Tag: 2017 wikitext editor |
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{{Chembox |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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|Watchedfields = changed |
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{{chembox |
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| verifiedrevid = 446276735 |
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|verifiedrevid = 470455423 |
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| ImageFile = Cyanogen-chloride.png |
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|ImageFile = Cyanogen-chloride.svg |
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|ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageSize = |
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|ImageSize = 100 |
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| ImageFile1 = Cyanogen-chloride-3D-vdW.png |
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|ImageName = Skeletal formula of cyanogen chloride |
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| ImageSize1 = |
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| IUPACName = Cyanic chloride |
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|ImageFileL1 = Cyanogen-chloride-3D-balls.png |
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|ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| OtherNames = Chloroformonitrile, Chlorine cyanide, Carbononitridic chloride, CK |
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|ImageNameL1 = Ball and stick model of cyanogen chloride |
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| Section1 = {{Chembox Identifiers |
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|ImageFileR1 = Cyanogen-chloride-3D-vdW.png |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ChemSpiderID = 10045 |
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|ImageNameR1 = Spacefill model of cyanogen chloride |
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| InChIKey = QPJDMGCKMHUXFD-UHFFFAOYAQ |
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|PIN = Carbononitridic chloride |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|SystematicName = Chloroformonitrile |
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| StdInChI = 1S/CClN/c2-1-3 |
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|OtherNames = {{Unbulleted list |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|Chlorine cyanide |
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| StdInChIKey = QPJDMGCKMHUXFD-UHFFFAOYSA-N |
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|Cyanic chloride |
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| CASNo = 506-77-4 |
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|Chlorocyanogen |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|Chlorcyan |
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| EINECS = 208-052-8 |
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|Chlorocyanide |
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| PubChem = 10477 |
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| SMILES = ClC#N |
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| InChI = 1/CClN/c2-1-3 |
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| RTECS = GT2275000 |
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| UNNumber = 1589 |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = CNCl |
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| MolarMass = 61.46 g/mol |
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| Appearance = colorless gas |
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| Density (0 °C, 101.325 ]) 2,7683 g/L |
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| Density = 1.186 g/cm<sup>3</sup> (liquid) |
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| MeltingPt = −6 °C |
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| BoilingPt = 13 °C<ref>{{RubberBible87th}}</ref> |
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| Solubility = Soluble |
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| VaporPressure = 1987 kPa (21.1 °C) |
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}} |
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| Section3 = {{Chembox Hazards |
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| ExternalMSDS = |
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| MainHazards =Highly toxic<ref>http://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750039.html</ref> |
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| FlashPt = |
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| NFPA-H = 4 |
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| NFPA-F = 0 |
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| NFPA-R = 2 |
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| NFPA-O = |
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}} |
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| Section8 = {{Chembox Related |
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| OtherFunctn = ]<br/>]<br/>] |
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| Function = cyanogen halides |
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| OtherCpds = ] |
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}} |
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}} |
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}} |
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|Section1={{Chembox Identifiers |
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|Abbreviations = CK |
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|CASNo = 506-77-4 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = 697I61NSA0 |
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|PubChem = 10477 |
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|ChemSpiderID = 10045 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|EINECS = 208-052-8 |
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|UNNumber = 1589 |
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|MeSHName = cyanogen+chloride |
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|RTECS = GT2275000 |
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|SMILES = ClC#N |
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|StdInChI = 1S/CClN/c2-1-3 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = QPJDMGCKMHUXFD-UHFFFAOYSA-N |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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|Section2={{Chembox Properties |
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|Properties_ref = <ref>{{RubberBible87th}}</ref> |
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|Formula = CNCl |
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|MolarMass = 61.470 g mol<sup>−1</sup> |
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|Appearance = Colorless gas |
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|Odor = acrid |
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|Density = 2.7683 mg mL<sup>−1</sup> (at 0 °C, 101.325 kPa) |
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|MeltingPtC = −6.55 |
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|BoilingPtC = 13 |
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|Solubility = soluble |
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|SolubleOther = soluble in ], ] |
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|VaporPressure = 1.987 MPa (at 21.1 °C) |
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|MagSus = -32.4·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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|Section3={{Chembox Thermochemistry |
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|DeltaHf = 137.95 kJ mol<sup>−1</sup> |
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|Entropy = 236.33 J K<sup>−1</sup> mol<sup>−1</sup> |
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}} |
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|Section4={{Chembox Hazards |
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|ExternalSDS = |
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|MainHazards = Highly toxic;<ref name=niosh>{{ cite web | url = https://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750039.html | title = CYANOGEN CHLORIDE (CK)| work = The Emergency Response Safety and Health Database | date = 9 July 2021| publisher = NIOSH }}</ref> forms ] in the body<ref name=PGCH/> |
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|GHSPictograms = {{GHS05}} {{GHS06}} {{GHS09}} |
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|GHSSignalWord = '''DANGER''' |
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|NFPA-H = 4 |
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|NFPA-F = 0 |
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|NFPA-R = 2 |
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|PEL = none<ref name=PGCH>{{PGCH|0162}}</ref> |
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|IDLH = N.D.<ref name=PGCH/> |
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|REL = C 0.3 ppm (0.6 mg/m<sup>3</sup>)<ref name=PGCH/> |
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|FlashPt = nonflammable |
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|FlashPt_ref = <ref name=PGCH/> |
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}} |
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|Section5={{Chembox Related |
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|OtherFunction_label = alkanenitriles |
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|OtherFunction = {{Unbulleted list|]|]|]|]|]|]|]|]|]}} |
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}} |
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}} |
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'''Cyanogen chloride''' is a highly ] chemical compound with the ] CNCl. This linear, triatomic ] is an easily condensed colorless gas. More commonly encountered in the laboratory is the related compound ], a room-temperature solid that is widely used in biochemical analysis and preparation. |
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==Synthesis, basic properties, structure== |
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Cyanogen chloride is a molecule with the connectivity {{chem2|Cl\sC\tN}}. Carbon and chlorine are linked by a ], and carbon and nitrogen by a ]. It is a linear molecule, as are the related cyanogen halides (NCF, ], NCI). Cyanogen chloride is produced by the oxidation of ] with ]. This reaction proceeds via the intermediate ] ({{chem2|(CN)2}}).<ref>{{ Cite book |author1=Coleman, G. H. |title=Inorganic Syntheses |author2=Leeper, R. W. |author3=Schulze, C. C. | chapter = Cyanogen Chloride | year = 1946 | volume = 2 | pages = 90–94 | doi = 10.1002/9780470132333.ch25 |isbn=9780470132333 }}</ref> |
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:<chem>NaCN + Cl2 -> ClCN + NaCl</chem> |
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The compound ]izes in the presence of acid to the heterocycle called ]. |
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Cyanogen chloride is slowly ] by water at neutral ] to release cyanate and chloride ions: |
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:<chem>ClCN + H2O -> NCO- + Cl- + 2H+</chem> |
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==Applications in synthesis== |
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Cyanogen chloride is a precursor to the sulfonyl cyanides<ref>{{ OrgSynth | author = Vrijland, M. S. A. | title = Sulfonyl Cyanides: Methanesulfonyl Cyanide | year = 1977 | volume = 57 | pages = 88 | collvol = 6 | collvolpages = 727 | prep = cv6p0727 | url = http://www.orgsyn.org/orgsyn/pdfs/CV6P0727.pdf }}</ref> and ], a useful reagent in ].<ref>{{ OrgSynth | author = Graf, R. | title = Chlorosulfonyl Isocyanate | year = 1966 | volume = 46 | pages = 23 | collvol = 5 | collvolpages = 226 | prep = cv5p0226 | url = http://www.orgsyn.org/orgsyn/pdfs/CV5P0226.pdf}}</ref> |
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Further chlorination gives the ]. |
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==Safety== |
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Also known as '''CK''', cyanogen chloride is a highly toxic ], and was once proposed for use in ]. It causes immediate injury upon contact with the eyes or respiratory organs. Symptoms of exposure may include ], ] (runny nose), ], ]ing, ], ], ], ], ], ]s, ], and death.<ref name=niosh/> It is especially dangerous because it is capable of penetrating the filters in ]s, according to United States analysts. CK is unstable due to ], sometimes with explosive violence.<ref name="FM 3-8">{{cite book | title = FM 3-8 Chemical Reference Handbook | publisher = US Army | year = 1967}}</ref> |
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==Chemical weapon== |
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Cyanogen chloride is listed in ] of the ]: all production must be reported to the ].<ref>{{Cite web|url=https://www.opcw.org/chemical-weapons-convention/annexes/annex-on-chemicals/schedule-3/|title=Schedule 3 |publisher= www.opcw.org|access-date=16 March 2018}}</ref> |
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By 1945, the U.S. Army's ] developed chemical warfare rockets intended for the new M9 and M9A1 ]s. An M26 Gas Rocket was adapted to fire cyanogen chloride-filled warheads for these rocket launchers.<ref name="Smart, Jeffrey 1997 p. 32">{{Citation | last = Smart | first = Jeffrey | title = History of Chemical and Biological Warfare: An American Perspective | chapter = 2 | place = Aberdeen, MD, USA | publisher = Army Chemical and Biological Defense Command | year = 1997 | page = 32}}.</ref> As it was capable of penetrating the protective filter barriers in some gas masks,<ref>{{Cite web|url=https://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750039.html|title = Cyanogen chloride (CK): Systemic Agent | NIOSH | CDC|date = 9 July 2021}}</ref> 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.<ref name="Smart, Jeffrey 1997 p. 32" /><ref>{{Citation | title = Field Manual 3-5 | contribution = Characteristics and Employment of Ground Chemical Munitions | place = Washington, DC | publisher = War Department | year = 1946 | pages = 108–19}}</ref><ref>{{Citation | last = Skates | first = John R | title = The Invasion of Japan: Alternative to the Bomb | publisher = ] | year = 2000 | isbn = 978-1-57003-354-4 | pages = 93–96}}</ref> The US added the weapon to its arsenal, and considered using it, along with ], as part of ], the planned invasion of Japan, but President ] decided against it, instead using the atomic bombs developed by the secret ].<ref>{{cite web |url=https://www.youtube.com/watch?v=8CFPaSH84ZU |title=How would have WW2 gone if the US had not used nuclear bombs on Japan? |author=Binkov's Battlegrounds |date=April 27, 2022 |website=YouTube.Com |publisher= |access-date=June 23, 2022 }}</ref> The CK rocket was never deployed or issued to combat personnel.<ref name="Smart, Jeffrey 1997 p. 32"/> |
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==References== |
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{{Reflist}} |
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==External links== |
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* {{ Cite journal | url = http://www.emedicine.com/emerg/topic910.htm | title = Cyanogen Chloride Poisoning | year = 2011 | author = Murphy-Lavoie, H. | publisher = MedScape | journal = EMedicine }} |
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* {{ cite web | url = http://www.npi.gov.au/substances/cyanide/index.html | title = National Pollutant Inventory – Cyanide compounds fact sheet | publisher = Australian Government }} |
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* {{ cite web | url = https://www.cdc.gov/niosh/npg/npgd0162.html | title = NIOSH Pocket Guide to Chemical Hazards | publisher = Centers for Disease Control and Prevention }} |
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{{Cyanides}} |
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{{Chemical warfare}} |
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{{Use dmy dates|date=March 2018}} |
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] |
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] |
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] |