Editing Cyanogen chloride

{{Chembox
|Watchedfields = changed
|verifiedrevid = 470455423
|ImageFile = Cyanogen-chloride.svg
|ImageFile_Ref = {{chemboximage|correct|??}}
|ImageSize = 100
|ImageName = Skeletal formula of cyanogen chloride
|ImageFileL1 = Cyanogen-chloride-3D-balls.png
|ImageFileL1_Ref = {{chemboximage|correct|??}}
|ImageNameL1 = Ball and stick model of cyanogen chloride
|ImageFileR1 = Cyanogen-chloride-3D-vdW.png
|ImageFileR1_Ref = {{chemboximage|correct|??}}
|ImageNameR1 = Spacefill model of cyanogen chloride
|PIN = Carbononitridic chloride
|SystematicName = Chloroformonitrile
|OtherNames = {{Unbulleted list|Chlorine cyanide|Cyanic chloride|Chlorocyanogen|Chlorcyan|Chlorocyanide|CK}}
|Section1={{Chembox Identifiers
|Abbreviations = CK
|CASNo = 506-77-4
|CASNo_Ref = {{cascite|correct|CAS}}
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 697I61NSA0
|PubChem = 10477
|ChemSpiderID = 10045
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|EINECS = 208-052-8
|UNNumber = 1589
|MeSHName = cyanogen+chloride
|RTECS = GT2275000
|SMILES = ClC#N
|StdInChI = 1S/CClN/c2-1-3
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = QPJDMGCKMHUXFD-UHFFFAOYSA-N
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
|Properties_ref = <ref>{{RubberBible87th}}</ref>
|Formula = ClCN
|MolarMass = 61.470 g/mol
|Appearance = Colorless gas
|Odor = acrid
|Density = 2.7683 mg/cm<sup>3</sup> (at 0&nbsp;°C, 101.325 kPa)
|MeltingPtC = −6.55
|BoilingPtC = 13
|Solubility = soluble
|SolubleOther = soluble in [[ethanol]], [[diethyl ether|ether]]
|VaporPressure = 1.987 MPa (at 21.1&nbsp;°C)
|MagSus = −32.4·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
|Section3={{Chembox Thermochemistry
|DeltaHf = 137.95 kJ/mol
|Entropy = 236.33 J/(mol·K)
}}
|Section4={{Chembox Hazards
|ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics1053.htm inchem.org]
|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 [[cyanide]] in the body<ref name=PGCH/>
|GHSPictograms = {{GHS05}} {{GHS06}} {{GHS09}}
|GHSSignalWord = '''DANGER'''
|NFPA-H = 4
|NFPA-F = 0
|NFPA-R = 2
|PEL = none<ref name=PGCH>{{PGCH|0162}}</ref>
|IDLH = N.D.<ref name=PGCH/>
|REL = C 0.3 ppm (0.6 mg/m<sup>3</sup>)<ref name=PGCH/>
|FlashPt = nonflammable
|FlashPt_ref = <ref name=PGCH/>
}}
|Section5={{Chembox Related
|OtherFunction_label = alkanenitriles
|OtherFunction = {{Unbulleted list|[[Hydrogen cyanide]]|[[Thiocyanic acid]]|[[Cyanogen iodide]]|[[Cyanogen bromide]]|[[Cyanogen fluoride]]|[[Acetonitrile]]|[[Aminoacetonitrile]]|[[Glycolonitrile]]|[[Cyanogen]]}}
}}
}}
'''Cyanogen chloride''' is an [[inorganic compound]] with the [[chemical formula|formula]] {{chem2|ClCN|auto=1}}. This 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 used in biochemical analysis and preparation. Cyanogen compounds are highly [[toxicity|toxic]].

==Synthesis, basic properties, structure==
Cyanogen chloride is a [[Linear molecular geometry|linear]] molecule with the connectivity {{chem2|Cl\sC\tN}}, as are [[Hydrogen cyanide|HCN]] and the related cyanogen halides ([[Cyanogen fluoride|FCN]], [[cyanogen bromide|BrCN]], [[Cyanogen iodide|ICN]]). The carbon and chlorine atoms are linked by a [[single bond]], and carbon and nitrogen by a [[triple bond]]. It is a linear molecule. Cyanogen chloride is produced by the oxidation of [[sodium cyanide]] with [[chlorine]]. This reaction proceeds via the intermediate [[cyanogen]] ({{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>
:{{chem2|NaCN + Cl2 → ClCN + [[sodium chloride|NaCl]]}}
The compound [[trimer (chemistry)|trimer]]izes in the presence of acid to the heterocycle called [[cyanuric chloride]].

Cyanogen chloride is slowly [[hydrolyzed]] by water at neutral [[pH]] to release cyanate and chloride ions:
:{{chem2|ClCN + H2O → [[cyanate|[OCN]-]] + [[Chloride|Cl-]] + 2 H+}}

==Applications in synthesis==
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}}</ref> and [[chlorosulfonyl isocyanate]], a useful reagent in [[organic synthesis]].<ref>{{OrgSynth | author = Graf, R. | title = Chlorosulfonyl Isocyanate | year = 1966 | volume = 46 | pages = 23 | collvol = 5 | collvolpages = 226 | prep = cv5p0226}}</ref>

Further chlorination gives the [[isocyanide dichloride]].

==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]], [[cough]]ing, [[confusion]], [[nausea]], [[vomiting]], [[edema]], [[Fainting|loss of consciousness]], [[convulsion]]s, [[paralysis]], and death.<ref name=niosh/> It is especially dangerous because it is capable of penetrating the filters in [[gas mask]]s, according to United States analysts. CK is unstable due to [[polymerization]], sometimes with explosive violence.<ref name="FM 3-8">{{cite book | title = FM 3-8 Chemical Reference Handbook | publisher = US Army | year = 1967}}</ref>

==Chemical weapon==
Cyanogen chloride is listed in [[List of Schedule 3 substances (CWC)|schedule 3]] of the [[Chemical Weapons Convention]]: all production must be reported to the [[Organisation for the Prohibition of Chemical Weapons|OPCW]].<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>

By 1945, the U.S. Army's [[Chemical Corps (United States Army)|Chemical Warfare Service]] developed chemical warfare rockets intended for the new M9 and M9A1 [[Bazooka]]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 &#124; NIOSH &#124; 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 = [[University of South Carolina Press]] | 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 [[hydrogen cyanide]], as part of [[Operation Downfall]], the planned invasion of Japan, but President [[Harry Truman]] decided against it, instead using the atomic bombs developed by the secret [[Manhattan Project]].<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"/>

==References==
{{Reflist}}

==External links==
* {{Cite journal | url = http://www.emedicine.com/emerg/topic910.htm | title = Cyanogen Chloride Poisoning | year = 2011 | author = Murphy-Lavoie, H. | publisher = MedScape | journal = EMedicine}}
* {{cite web | url = http://www.npi.gov.au/substances/cyanide/index.html | title = National Pollutant Inventory – Cyanide compounds fact sheet | publisher = Australian Government}}
* {{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}}

{{Cyanides}}
{{Chemical warfare}}

{{Use dmy dates|date=March 2018}}

[[Category:Chlorine compounds]]
[[Category:Triatomic molecules]]
[[Category:Cyano compounds]]
[[Category:Nonmetal halides]]
[[Category:Blood agents]]
[[Category:Pseudohalogens]]