Editing Cyanoacetylene

{{short description|Organic compound (HC≡C−C≡N)}}
{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 444463004
|Reference = <ref>{{cite journal | title = Cyanoacetylene. I. The synthesis and some chemical properties |author1=Murahashi, Shunsuke |author2=Takizawa, Takeo |author3=Kurioka, Shohei |author4=Maekawa, Seiji | journal = Nippon Kagaku Zasshi | year = 1956 | volume = 77 | pages = 1689–1692 | doi = 10.1246/nikkashi1948.77.1689 | issue = 11| doi-access = free}}</ref>
|ImageFile1 = Cyanoacetylene.png
|ImageFile2 = Cyanoacetylene-3D-vdW.png
|PIN = Prop-2-ynenitrile
|OtherNames = {{ubl|Propiolonitrile|Cyanoethyne|Monocyanoacetylene|2-Propynenitrile}}
|Section1 = {{Chembox Identifiers
|CASNo_Ref = {{cascite|correct|??}}
|CASNo=1070-71-9
|UNII_Ref = {{fdacite|correct|FDA}} 
|UNII = 0TF7QM91EF
|PubChem=14055
|SMILES=C#CC#N
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 13436
|InChI = 1/C3HN/c1-2-3-4/h1H
|InChIKey = LNDJVIYUJOJFSO-UHFFFAOYAB
|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
|StdInChI = 1S/C3HN/c1-2-3-4/h1H
|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
|StdInChIKey = LNDJVIYUJOJFSO-UHFFFAOYSA-N
}}
|Section2 = {{Chembox Properties
|C=3 | H=1 | N=1
|Appearance = Colorless liquid
|MeltingPtC=5
|BoilingPtC=42.5
}}
}}

'''Cyanoacetylene''' is an [[organic compound]] with the formula {{chem2|C3HN|auto=1}} or {{chem2|H\sC\tC\sC\tN}}. It is the simplest [[cyanopolyyne]]. Cyanoacetylene has been detected by [[spectroscopy|spectroscopic methods]] in [[interstellar cloud]]s,<ref>{{Cite journal | title = Interstellar molecules | author = Solomon, Philip M. | journal = Physics Today | year = 1973 | volume = 26 | issue = 3 | pages = 32–40 | doi=10.1063/1.3127983|bibcode = 1973PhT....26c..32S | doi-access = free}}</ref> in the [[Coma (cometary)|coma]] of [[comet Hale–Bopp]] and in the atmosphere of [[Saturn]]'s moon [[titan (moon)|Titan]],<ref>{{cite journal | title= The abundances of constituents of Titan's atmosphere from the GCMS instrument on the Huygens probe |author= H. B. Niemann |journal= [[Nature (journal)|Nature]] |volume=438 | issue= 7069 |pages=779–784 |year=2005 | pmid= 16319830 |doi=10.1038/nature04122 | bibcode=2005Natur.438..779N|display-authors=etal|url=https://deepblue.lib.umich.edu/bitstream/2027.42/62703/1/nature04122.pdf |hdl= 2027.42/62703 |s2cid= 4344046 |hdl-access=free}}</ref> where it sometimes forms expansive fog-like clouds.<ref>{{cite news | title=Cassini Detects Giant Cloud of Frozen Compounds on Saturn's Moon Titan |first= Enrico |last=de Lazaro |date=November 11, 2015|publisher= Sci News |url=http://www.sci-news.com/space/science-cassini-ice-cloud-saturns-moon-titan-03427.html}}</ref>

Cyanoacetylene is one of the molecules that was produced in the [[Miller–Urey experiment]].<ref>{{cite journal |title= Astrophysical and Astrochemical Insights into the Origin of Life| journal=Reports on Progress in Physics| volume=65| issue=10| pages=1427–1487| doi=10.1088/0034-4885/65/10/202| year=2002| last1=Ehrenfreund| first1=P.| last2=Irvine| first2=W.| last3=Becker| first3=L.| last4=Blank| first4=J.| last5=Brucato| first5=J. R.| last6=Colangeli| first6=L.| last7=Derenne| first7=S.| last8=Despois| first8=D.| last9=Dutrey| first9=A.| last10=Fraaije| first10=H.| last11=Lazcano| first11=A.| last12=Owen| first12=T.| last13=Robert| first13=F.| last14=Issi-Team| first14=an International Space Science Inst| bibcode=2002RPPh...65.1427E| url=https://digital.library.unt.edu/ark:/67531/metadc1406361/| url-access=subscription}}</ref>

:{{Chem2|H\sC\tC\sH + H\sC\tN → H\sC\tC\sC\tN + H2}}

[[Nickel carbonyl]] catalyzes cyanoacetylene [[carboalkoxylation]] to [[cyanoacrylate]] esters.<ref>{{Ullmann|author1=Ohara Takashi|author2=Sato Takahisa|author3=Shimizu Noboru|first4=G&uuml;nter|last4=Prescher|first5=Helmut|last5=Schwind|first6=Otto|last6=Weiberg|first7=Klaus|last7=Marten|first8=Helmut|last8=Greim|first9=Timothy&nbsp;D.|last9=Shaffer|first10=Partha|last10=Nandi|title=Acrylic acid and derivatives|year=2020|doi=10.1002/14356007.a01_161.pub4|p=17}}</ref>

==See also==
*[[Dicyanoacetylene]], N≡C−C≡C−C≡N
*[[Diacetylene]], H−C≡C−C≡C−H
*[[Cyanogen]], N≡C−C≡N
*[[Hydrocyanic acid]], H−C≡N
*[[Polyyne]], R−(C≡C)<sub>''n''</sub>−R

==References==
{{reflist}}
{{Molecules detected in outer space}}
{{Authority control}}

[[Category:Alkyne derivatives]]
[[Category:Conjugated nitriles]]