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			{{Short description|Chemical compound (CN)₂, functional group -CN-, or radical CN·}}
	{{about|the chemical compound|the Android firmware|CyanogenMod}}
			{{Distinguish|cyanamide|hydrogen cyanide|Cyanide}}
	{{chembox
			{{for|the Android distribution|CyanogenMod}}
	| verifiedrevid = 443544396
			{{Chembox
	| Name = '''Cyanogen'''
			| Watchedfields = changed
	| ImageFile_Ref = {{chemboximage|correct|??}}
			| verifiedrevid = 444495670
	| ImageFile = Cyanogen-2D-dimensions.png
			| ImageFile = Cyanogen.png
	| ImageSize = 200px
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageName = Cyanogen
			| ImageSize = 100
	| ImageFile1 = Cyanogen-3D-vdW.png
			| ImageName = Skeletal formula of cyanogen
	| ImageSize1 = 200px
			| ImageFileL1 = Cyanogen-3D-balls.png
	| IUPACName = Ethanedinitrile
			| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| OtherNames = Cyanogen<br />Carbon nitride<br />Dicyan<br />Dicyanogen<br />Nitriloacetonitrile<br />Oxalic acid dinitrile<br />Oxalonitrile<br />Oxalyl cyanide
			| ImageNameL1 = Ball and stick model of cyanogen
	| Section1 = {{Chembox Identifiers
			| ImageFileR1 = Cyanogen-3D-vdW.png
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ImageFileR1_Ref = {{chemboximage|correct|??}}
	| ChemSpiderID = 9605
			| ImageNameR1 = Spacefill model of cyanogen
			| PIN = Oxalonitrile<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 902 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
			| SystematicName = Ethanedinitrile<ref name=iupac2013 />
			| OtherNames = Cyanogen<br />Bis(nitridocarbon)(''C''—''C'')<ref name=ChEBI>{{Cite web|title=oxalonitrile (CHEBI:29308)| url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=29308|work=Chemical Entities of Biological Interest|publisher=European Bioinformatics Institute|access-date=6 June 2012|location=UK|date=27 October 2006|at=Main}}</ref><br />Dicyan<ref Name="Pocket">{{cite book |title=NIOSH Pocket Guide to Chemical Hazards|date=September 2007 |publisher=Department of Health and Human Services, Centers for Disease Control, National Institute for Occupational Safety & Health |page=82}}</ref><ref name = "Merck">{{cite book |title=The Merck Index|url=https://archive.org/details/merckindexencycl00wind|url-access=registration|edition=10th|year=1983|publisher=Merck & Co. |location=Rahway, NJ|page=|isbn=9780911910278}}</ref><br />Carbon nitride<ref Name="Pocket" /><br />Oxalic acid dinitrile<ref name="Merck" /><br />Dicyanogen<br />Nitriloacetonitrile<br />CY
			|Section1={{Chembox Identifiers
			| CASNo = 460-19-5
			| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 534Q0F66RK
	| PubChem = 9999		| PubChem = 9999
			| ChemSpiderID = 9605
	| InChI = 1/C2N2/c3-1-2-4
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| EINECS = 207-306-5
			| UNNumber = 1026
			| MeSHName = cyanogen
	| ChEBI = 29308		| ChEBI = 29308
			| ChEBI_Ref = {{ebicite|correct|EBI}}
			| RTECS = GT1925000
			| Beilstein = 1732464
			| Gmelin = 1090
	| SMILES = N#CC#N		| SMILES = N#CC#N
	| InChIKey = JMANVNJQNLATNU-UHFFFAOYAS
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C2N2/c3-1-2-4		| StdInChI = 1S/C2N2/c3-1-2-4
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = JMANVNJQNLATNU-UHFFFAOYSA-N		| StdInChIKey = JMANVNJQNLATNU-UHFFFAOYSA-N
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| CASNo = 460-19-5
			}}
	| CASNo_Ref = {{cascite|correct|CAS}}
			|Section2={{Chembox Properties
	| RTECS = GT1925000
			| C=2 | N=2
	| EINECS = 207-306-5
			| Appearance = Colourless gas
	| UNNumber = 1026
			| Odor = pungent, ]-like
	}}
			| Density = 950 mg mL<sup>−1</sup> (at −21&nbsp;°C)
	| Section2 = {{Chembox Properties
	| C = 2		| MeltingPtC = -28
	| N = 2		| BoilingPtK = 252.0
	| Density = 0.95 g/cm<sup>3</sup> (liquid, &minus;21 °C)		| Solubility = 45 g/100 mL (at 20&nbsp;°C)
			| SolubleOther = soluble in ], ]
	| Solubility = 450 mL/100 mL (20 °C)
			| HenryConstant = 1.9 μmol Pa<sup>−1</sup> kg<sup>−1</sup>
	| MeltingPtC = -28
			| RefractIndex = 1.327 (18&nbsp;°C)
	| BoilingPtC = -21
			| VaporPressure = 5.1 atm (21&nbsp;°C)<ref name=PGCH/>
	}}
			| MagSus = -21.6·10<sup>−6</sup> cm<sup>3</sup>/mol
	| Section7 = {{Chembox Hazards
			}}
	| ExternalMSDS =
			|Section3={{Chembox Thermochemistry
	| EUIndex = 608-011-00-8
			| DeltaHf = 309.07 kJ mol<sup>−1</sup>
	| EUClass = Flammable ('''F''')<br />Very Toxic ('''T+''')<br />Dangerous for the environment ('''N''')
			| DeltaHc = −1.0978–−1.0942 MJ mol<sup>−1</sup>
	| RPhrases = {{R11}}, {{R23}}, {{R50/53}}
			| Entropy = 241.57 J K<sup>−1</sup> mol<sup>−1</sup>
	| SPhrases = {{S1/2}}, {{S23}}, {{S45}}, {{S60}}, {{S61}}
			}}
	| NFPA-H = 4
			|Section4={{Chembox Hazards
	| NFPA-F = 4
			| ExternalSDS =
	| NFPA-R = 2
			| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS09}}
	| FlashPt = Flammable gas
			| GHSSignalWord = Danger
	| ExploLimits = 6.6–42.6%
			| HPhrases = {{H-phrases|220|331|410}}
	}}
			| PPhrases = {{P-phrases|210|261|271|273|304+340|311|321|377|381|391|403|403+233|405|501}}
	| Section8 = {{Chembox Related
			| NFPA-H = 4
	| OtherCpds = ]<br />]<br />]
			| NFPA-F = 4
	}}
			| NFPA-R = 2
			| ExploLimits = 6.6–32%<ref name=PGCH/>
			| PEL = none<ref name=PGCH>{{PGCH|0161}}</ref>
			| IDLH = N.D.<ref name=PGCH/>
			| REL = TWA 10 ppm (20 mg/m<sup>3</sup>)<ref name=PGCH/>
			| MainHazards = forms ] in the body; flammable<ref name=PGCH/>
			}}
			|Section5={{Chembox Related
			| OtherFunction_label = alkanenitriles
			| OtherFunction = {{Unbulleted list|]|]|]|]|]|]|]|]|]|]|]|]|]|]|]}}
			| OtherCompounds = ]
			}}
	}}		}}
			'''Cyanogen''' is the ] with the ] (]]){{sub|2}}. The simplest stable ], it is a ] and highly ] ] with a ] ]. The molecule is a ]. Cyanogen molecules consist of two CN groups ‒ analogous to diatomic halogen molecules, such as ]{{sub|2}}, but far less oxidizing. The two ] are bonded together at their ] atoms: N≡C‒C≡N, though other ]s have been detected.<ref>{{ cite journal |author1=Ringer, A. L. |author2=Sherrill, C. D. |author3=King, R. A. |author4=Crawford, T. D. | year = 2008 | title = Low-lying singlet excited states of isocyanogen | journal = International Journal of Quantum Chemistry | volume = 106 | issue = 6 | pages = 1137–1140 | doi = 10.1002/qua.21586 |bibcode = 2008IJQC..108.1137R }}</ref> The name is also used for the CN radical,<ref name=radical>{{cite book|doi=10.1007/978-3-642-11274-4_1806|chapter=Cyanogen Radical|title=Encyclopedia of Astrobiology|pages=402|year=2011|last1=Irvine|first1=William M.|isbn=978-3-642-11271-3}}</ref> and hence is used for compounds such as ] (NCBr)<ref>{{OrgSynth |author=Hartman, W. W. |author2=Dreger, E. E. |title=Cyanogen Bromide |year=1931 |volume=11 |pages=30 |collvol=2 |collvolpages=150 |url=http://www.orgsyn.org/orgsyn/pdfs/CV2P0150.pdf}}</ref> (but see also '']''). When burned at increased pressure with oxygen, it is possible to get a blue tinted flame, the temperature of which is about 4800°C (a higher temperature is possible with ozone). It is as such regarded as the gas with the second highest temperature of burning (after ]).
	'''Cyanogen''' is the ] with the ] (]])<sub>2</sub>. It is a ], toxic ] with a ] ].
	The molecule is a ]. Cyanogen molecules consist of two CN groups &mdash; analogous to diatomic halogen molecules, such as ]<sub>2</sub>, but far less oxidizing. The two ] groups are bonded together at their ] atoms: N≡C−C≡N, although other isomers have been detected.<ref>
	{{ Cite news
	| last = Ringer
	| first = Ashley
	| publication-date =
	| date = Jan 15
	| year = 2008
	| title = Low-lying singlet excited states of isocyanogen
	| periodical = International Journal of Quantum Chemistry
	| publisher = Wiley
	| volume = 106
	| issue = 6
	| pages = 1137–1140
	| postscript = <!--None-->
	}}</ref>
	Certain derivatives of cyanogen are also called “cyanogen” even though they contain only one CN group. For example ] has the formula NCBr.<ref>Hartman W. W.; Dreger, E. E.
	"Cyanogen Bromide" Organic Syntheses, Collected Volume 2, p.150 (1943).http://www.orgsyn.org/orgsyn/pdfs/CV2P0150.pdf</ref>
	Cyanogen is the ] of ]:		Cyanogen is the ] of ]:
	:H<sub>2</sub>NC(O)C(O)NH<sub>2</sub> → NCCN + 2 H<sub>2</sub>O		:{{chem2|H2NC(O)C(O)NH2 → NCCN + 2 H2O}}
			though oxamide is manufactured from cyanogen by hydrolysis:<ref name=greenwood>{{Greenwood&Earnshaw2nd|pages=320–321}}</ref>
			:{{chem2|NCCN + 2 H2O → H2NC(O)C(O)NH2}}
	==Preparation==		==Preparation==
	Cyanogen is typically generated from cyanide compounds. One laboratory method entails thermal decomposition of ]:		Cyanogen is typically generated from ] compounds. One laboratory method entails thermal decomposition of ]:
	:2 Hg(CN)<sub>2</sub> → (CN)<sub>2</sub> + Hg<sub>2</sub>(CN)<sub>2</sub>		:{{chem2|2 Hg(CN)2 → (CN)2 + Hg2(CN)2}}
	Alternatively, one can combine solutions of copper(II) salts (such as ]) with cyanides, an unstable copper(II) cyanide is formed which rapidly decomposes into ] and cyanogen.<ref>{{cite journal		Or, one can combine solutions of copper(II) salts (such as ]) with cyanides; an unstable copper(II) cyanide is formed which rapidly decomposes into ] and cyanogen.<ref>{{cite journal | title = The Synthesis And Chemistry Of Cyanogen |author1=Brotherton, T. K. |author2=Lynn, J. W. | journal = ] | year = 1959 | volume = 59 | issue = 5 | pages = 841–883 | doi = 10.1021/cr50029a003 }}</ref>
			:{{chem2|2 CuSO4 + 4 KCN → (CN)2 + 2 CuCN + 2 K2SO4}}
	| title = The Synthesis And Chemistry Of Cyanogen
	| author = T. K. Brotherton, J. W. Lynn
	| journal = ]
	| volume = 59
	| issue = 5
	| pages = 841–883
	| year = 1959
	| doi = 10.1021/cr50029a003}}
	</ref>
	:2 CuSO<sub>4</sub> + 4 KCN → (CN)<sub>2</sub> + 2 CuCN + 2 K<sub>2</sub>SO<sub>4</sub>
	Industrially, it is created by the ] of ], usually using ] over an activated ] ] or ] over a ] salt. It is also formed when ] and ] are reacted by an electrical spark or discharge.<ref>{{cite journal		Industrially, it is created by the ] of ], usually using ] over an activated ] ] or ] over a ] salt. It is also formed when ] and ] are reacted by an electrical spark or discharge.<ref>{{cite journal |title=The Fixation of Atmospheric Nitrogen |author= Breneman, A. A. |journal=] |volume=11 |issue=1 |pages=2–27 |date=January 1889 |doi=10.1021/ja02126a001|url= https://zenodo.org/record/1428969 }}</ref>
	| title = Showing the Progress and Development of Processes for the manufacture of Cyanogen and its Derivates (in: THE FIXATION OF ATMOSPHERIC NITROGEN
			==Isomers==
	| author = A. A. Breneman
			Cyanogen is NCCN. There are less stable isomers in which the order of the atoms differs. Isocyanogen (or cyanoisocyanogen) is NCNC, diisocyanogen is CNNC, and diazodicarbon{{Citation needed|date=February 2020}} is CCNN.
	| journal = ]
	| volume = 11
	| issue = 1
	| pages = 2–28
	| year = 1959
	| doi = 10.1021/ja02126a001}}</ref>
	==Paracyanogen==		==Paracyanogen==
			] Paracyanogen is a ] of cyanogen. It can be best prepared by heating ]. It can also be prepared by heating ], ], ] or cyanuric iodide.<ref>{{cite journal |last= Bircumshaw |first= L. L. |author2=F. M. Tayler |author3=D. H. Whiffen |year=1954 |title= Paracyanogen: its formation and properties. Part I| journal= J. Chem. Soc. |pages=931–935 |doi=10.1039/JR9540000931}}</ref> It can also be prepared by the polymerization of cyanogen at {{convert|300|to|500|C}} in the presence of trace impurities. Paracyanogen can also be converted back to cyanogen by heating to {{convert|800|C}}.<ref name=greenwood/> Based on experimental evidence, the structure of this polymeric material is thought to be rather irregular, with most of the ] atoms being of ] and localized domains of ].<ref>{{cite journal|author=Maya, Leon|year=1993|journal=Journal of Polymer Science Part A|volume= 31|issue=10|pages= 2595–2600|title=Paracyanogen Reexamined |doi=10.1002/pola.1993.080311020 |bibcode=1993JPoSA..31.2595M |url=https://zenodo.org/record/1229357 |type=Submitted manuscript}}</ref>
	Paracyanogen is produced by polymerization of cyanogen through pyrolysis of heavy metal cyanides.<ref> Paracyanogen</ref>
	==Astronomy==
	Cyanogen is used to measure the temperature of interstellar gas clouds<ref>http://www.mendeley.com/research/interstellar-cyanogen-temperature-cosmic-microwave-background-radiation/</ref>.
	==History==		==History==
	Cyanogen was first synthesized in 1815 by ], who determined its empirical formula and named it.<ref>Joseph Louis Gay-Lussac (1815) ''Annales de chimie'', vol. 95, pages 136-231. On page 163 of this article, Gay-Lussac coined the word "cyanogène" from the Greek words κύανος (kyanos, blue) and γεννάω (gennao, I create), because cyanide was first isolated by the Swedish chemist ] from the pigment "]".</ref> It attained importance with the growth of the ] industry in the late nineteenth century and is still an important intermediate in the production of many fertilizers. It is also used as a stabilizer in the production of ].		Cyanogen was first synthesized in 1815 by ], who determined its empirical formula and named it. Gay-Lussac coined the word "cyanogène" from the Greek words κυανός (kyanos, blue) and γεννάω (gennao, to create), because cyanide was first isolated by Swedish chemist ] from the pigment ].<ref>{{ cite journal | author = Gay-Lussac, J. L. | title = Recherches sur l'acide prussique | journal = Annales de Chimie | date = 1815 | volume = 95 | pages = 136–231 | url = https://books.google.com/books?id=m9s3AAAAMAAJ&pg=PA136 |language=fr}} Gay-Lussac names cyanogen on p. 163.</ref> It attained importance with the growth of the ] industry in the late 19th century and remains an important intermediate in the production of many fertilizers. It is also used as a stabilizer in the production of ].
			Cyanogen is commonly found in ]s.<ref name="poison">{{cite web | title=Cometary Poison Gas Geyser Heralds Surprises | website=science.nasa.gov | date=2010-11-02 | url=https://science.nasa.gov/science-news/science-at-nasa/2010/02nov_epoxi2/ | archive-url=https://web.archive.org/web/20101106033738/https://science.nasa.gov/science-news/science-at-nasa/2010/02nov_epoxi2/ | archive-date=2010-11-06 | url-status=dead}}</ref> In 1910 a ] analysis of ] found cyanogen in the comet's tail, which led to public fear that the Earth would be poisoned as it passed through the tail. People in ] wore gas masks, and merchants sold ] "comet pills" claimed to neutralize poisoning.<ref name="poison" /> Because of the extremely diffuse nature of the tail, there was no effect when the planet passed through it.<ref>{{cite news |url=https://timesmachine.nytimes.com/timesmachine/1910/02/08/104920328.pdf |title=Comet's Poisonous Tail |newspaper=New York Times |date=1910-02-08}}</ref><ref>{{cite web | title=Halley's Comet 100 years ago | website=The Denver Post | date=2010-05-25 | url=https://www.denverpost.com/2010/05/25/halleys-comet-100-years-ago/}}</ref>
	==Safety==		==Safety==
	Like other inorganic ]s, cyanogen is very toxic, as it undergoes reduction to ], which binds more strongly than oxygen to the ] complex, thus interrupting the ] ]. Cyanogen gas is an irritant to the eyes and respiratory system. Inhalation can lead to headache, dizziness, rapid pulse, nausea, vomiting, loss of consciousness, convulsions, and death, depending on exposure.<ref name="HitCL">Muir, GD (ed.) 1971, ''Hazards in the Chemical Laboratory'', The Royal Institute of Chemistry, London.</ref>		Like other ]s, cyanogen is very toxic, as it readily undergoes reduction to cyanide, which poisons the ] complex, thus interrupting the ]l ]. Cyanogen gas is an irritant to the eyes and respiratory system. Inhalation can lead to headache, dizziness, rapid pulse, nausea, vomiting, loss of consciousness, convulsions, and death, depending on exposure.<ref name="HitCL">{{ cite book | editor = Muir, G. D. | year = 1971 | title = Hazards in the Chemical Laboratory | publisher = The Royal Institute of Chemistry | location = London }}</ref> Lethal dose through inhalation typically ranges from {{convert|100|to|150|mg|gr|abbr=off|lk=on}}.
			Cyanogen produces the second-hottest-known natural flame (after ] aka carbon subnitride) with a temperature of over {{convert|4525|C}} when it burns in oxygen.<ref>{{ cite journal |author1=Thomas, N. |author2=Gaydon, A. G. |author3=Brewer, L. | title = Cyanogen Flames and the Dissociation Energy of N<sub>2</sub> | journal = The Journal of Chemical Physics | year = 1952 | volume = 20 | issue = 3 | pages = 369–374 | doi = 10.1063/1.1700426 | bibcode = 1952JChPh..20..369T }}</ref><ref>{{ cite journal |author1=J. B. Conway |author2=R. H. Wilson Jr. |author3=A. V. Grosse |title=The Temperature of the Cyanogen-Oxygen Flame | journal = Journal of the American Chemical Society | year = 1953 | volume = 75 | issue = 2 | pages = 499 | doi = 10.1021/ja01098a517 }}</ref>
			==In popular culture==
			In the '']'' serial "]" (the 5th serial of season 13), the Doctor synthesizes cyanogen using hydrogen cyanide as a starting material and vents it through a pipe to stop Solon from performing surgery on the brain of Morbius's body.
			In '']'' (1987) Friday (Dan Aykroyd) and Streebek (Tom Hanks) are tracking down the villain who stole "the pseudohalogenic compound cyanogen".<ref>{{cite web|url=https://getyarn.io/yarn-clip/f528f11d-6d18-4f71-b3e0-874f23325b97|title=The trichlornitromethane and the pseudo-halogenic compound cyanogen|access-date=August 18, 2021}}</ref>
	Cyanogen produces the second hottest known natural flame (after ]) with a temperature of over 4525&nbsp;°C when it burns in oxygen.<ref>{{Cite journal
	| last = Thomas
	| first =N.
	| author-link =
	| last2 =Gaydon, A. G.; Brewer, L.
	| first2 =A. G.
	| author2-link =
	| title = Cyanogen Flames and the Dissociation Energy of N2
	| journal =The Journal of Chemical Physics
	| volume =20
	| issue =3
	| pages =369–374
	| date =March 1952
	| year =
	| url =http://scitation.aip.org/getabs/servlet/GetabsServlet?prog=normal&id=JCPSA6000020000003000369000001&idtype=cvips&gifs=yes
	| doi =10.1063/1.1700426
	| id =
	| last3 = Brewer
	| first3 = L.
	| postscript =
	| bibcode=1952JChPh..20..369T}}</ref>
	==See also==		==See also==
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	==References==		==References==
	{{reflist}}		{{Reflist|30em}}
	==External links==		==External links==
	{{commons category|cyanogen}}		* {{Commons category inline|Cyanogen}}
			* {{Cite EB1911|wstitle=Cyanogen}}
	*
			*
	*
			*
			*
			{{Chemical agents}}
	]
			{{Cyanides}}
	]
	]		{{Nitrogen compounds}}
			{{Molecules detected in outer space}}
			{{Authority control}}
			]
	]
			]
	]
			]
	]
			]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
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	]
	]