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Cyanoacetylene

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Organic compound (HC≡C–C≡N)

Cyanoacetylene^[1]
Names


Preferred IUPAC name Prop-2-ynenitrile
Other names Propiolonitrile Cyanoethyne Monocyanoacetylene 2-Propynenitrile
Identifiers
CAS Number	1070-71-9^Y
3D model (JSmol)	Interactive image
ChemSpider	13436^Y
ECHA InfoCard	100.313.512
PubChem CID	14055
UNII	0TF7QM91EF^Y
CompTox Dashboard(EPA)	DTXSID40147867
InChI InChI=1S/C3HN/c1-2-3-4/h1H^N Key: LNDJVIYUJOJFSO-UHFFFAOYSA-N^N InChI=1/C3HN/c1-2-3-4/h1H Key: LNDJVIYUJOJFSO-UHFFFAOYAB
SMILES C#CC#N
Properties
Chemical formula	C₃HN
Molar mass	51.048 g·mol⁻¹
Appearance	Colorless liquid
Melting point	5 °C (41 °F; 278 K)
Boiling point	42.5 °C (108.5 °F; 315.6 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Cyanoacetylene is anorganic compound with the formulaC₃H N orH−C≡C−C≡N. It is the simplestcyanopolyyne. Cyanoacetylene has been detected byspectroscopic methods ininterstellar clouds,^[2] in thecoma ofcomet Hale–Bopp and in the atmosphere ofSaturn's moonTitan,^[3] where it sometimes forms expansive fog-like clouds.^[4]

Cyanoacetylene is one of the molecules that was produced in theMiller–Urey experiment.^[5]

H−C≡C−H + H−C≡N → H−C≡C−C≡N + H₂

Nickel carbonyl catalyzes cyanoacetylenecarboalkoxylation tocyanoacrylate esters.^[6]

References

[edit]

^Murahashi, Shunsuke; Takizawa, Takeo; Kurioka, Shohei; Maekawa, Seiji (1956)."Cyanoacetylene. I. The synthesis and some chemical properties".Nippon Kagaku Zasshi.77 (11):1689–1692.doi:10.1246/nikkashi1948.77.1689.
^Solomon, Philip M. (1973)."Interstellar molecules".Physics Today.26 (3):32–40.Bibcode:1973PhT....26c..32S.doi:10.1063/1.3127983.
^H. B. Niemann; et al. (2005)."The abundances of constituents of Titan's atmosphere from the GCMS instrument on the Huygens probe"(PDF).Nature.438 (7069):779–784.Bibcode:2005Natur.438..779N.doi:10.1038/nature04122.hdl:2027.42/62703.PMID 16319830.S2CID 4344046.
^de Lazaro, Enrico (November 11, 2015)."Cassini Detects Giant Cloud of Frozen Compounds on Saturn's Moon Titan". Sci News.
^Ehrenfreund, P.; Irvine, W.; Becker, L.; Blank, J.; Brucato, J. R.; Colangeli, L.; Derenne, S.; Despois, D.; Dutrey, A.; Fraaije, H.; Lazcano, A.; Owen, T.; Robert, F.; Issi-Team, an International Space Science Inst (2002)."Astrophysical and Astrochemical Insights into the Origin of Life".Reports on Progress in Physics.65 (10):1427–1487.Bibcode:2002RPPh...65.1427E.doi:10.1088/0034-4885/65/10/202.
^Ohara Takashi; Sato Takahisa; Shimizu Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut; Shaffer, Timothy D.; Nandi, Partha (2020). "Acrylic acid and derivatives".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 17.doi:10.1002/14356007.a01_161.pub4.ISBN 978-3-527-30673-2.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)

Molecules detected in outer space

Molecules

Diatomic	Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Imidogen Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur mononitride Sulfur monoxide Titanium(II) oxide
Triatomic	Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene Methylidynephosphane N₂H⁺ Nitrous oxide Nitroxyl Ozone Potassium cyanide Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Trihydrogen cation Water
Four atoms	Acetylene Ammonia Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methyl cation Methyl radical Methylene amidogen Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thiocyanic acid Thioformaldehyde Tricarbon monosulfide Tricarbon monoxide
Five atoms	Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster
Six atoms	Acetonitrile Cyanobutadiynyl radical Cyclopropenone Diacetylene E-Cyanomethanimine Ethylene Formamide HC₄N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene
Seven atoms	Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Methyl isocyanate Methylamine Propyne Vinyl alcohol
Eight atoms	Acetic acid Acrolein Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methyl formate Methylcyanoacetylene
Nine atoms	Acetamide Cyanohexatriyne Dimethyl ether Ethanethiol Ethanol Methyldiacetylene N-Methylformamide Octatetraynyl radical Propene Propionitrile
Ten atoms or more	Acetone Benzene Benzonitrile Buckminsterfullerene (C₆₀, C₆₀⁺, fullerene, buckyball) Butyronitrile C₇₀ fullerene Cyanodecapentayne Cyclopentindene Ethyl formate Ethylene glycol Heptatrienyl radical Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Pyrimidine