Cyanoacetylene

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
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
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 their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Cyanoacetylene is an organic compound with formula C₃HN or H−C≡C−C≡N. It is the simplest cyanopolyyne. Cyanoacetylene has been detected by spectroscopic methods in interstellar clouds,^[2] in the coma of comet Hale–Bopp and in the atmosphere of Saturn's moon Titan,^[3] where it sometimes forms expansive fog-like clouds.^[4]

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

{\ce {H-C#C-H + H-C#N -> H-C#C-C#N + H2}}

References

^ 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.

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 Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Imidogen Sulfur mononitride Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur monohydride 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 radical N₂H⁺ Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water
Four atoms	Acetylene Ammonia Cyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl cation Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon monosulfide Thiocyanic acid
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 E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC₄N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene
Seven atoms	Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Methylacetylene Methylamine Methyl isocyanate Vinyl alcohol
Eight atoms	Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Propenal
Nine atoms	Acetamide Cyanohexatriyne Cyanotriacetylene Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Propionitrile
Ten atoms or more	Acetone Benzene Benzonitrile Buckminsterfullerene (C₆₀, C₆₀⁺, fullerene, buckyball) C₇₀ fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propyl cyanide Pyrimidine Heptatrienyl radical