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Cyanoacetylene

Names
Preferred IUPAC name Prop-2-ynenitrile
Other names Propiolonitrile Cyanoethyne Monocyanoacetylene 2-Propynenitrile
Identifiers
CAS Number	1070-71-9
3D model (JSmol)	Interactive image
ChemSpider	13436
PubChem CID	14055
UNII	0TF7QM91EF
CompTox Dashboard (EPA)	DTXSID40147867
InChI InChI=1S/C3HN/c1-2-3-4/h1HKey: LNDJVIYUJOJFSO-UHFFFAOYSA-N InChI=1/C3HN/c1-2-3-4/h1HKey: LNDJVIYUJOJFSO-UHFFFAOYAB
SMILES C#CC#N
Properties
Chemical formula	C3HN
Molar mass	51.048 g·mol
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 , 100 kPa). N verify (what is  ?) Infobox references

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

Cyanoacetylene is one of the molecules that was produced in the Miller–Urey experiment.

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

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)_n−R

References

1. 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.
2. Solomon, Philip M. (1973). "Interstellar molecules". Physics Today. 26 (3): 32–40. Bibcode:1973PhT....26c..32S. doi:10.1063/1.3127983.
3. 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.
4. de Lazaro, Enrico (November 11, 2015). "Cassini Detects Giant Cloud of Frozen Compounds on Saturn's Moon Titan". Sci News.
5. 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.

v t e 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 Sulfanyl 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 N2H Nitrous oxide Nitroxyl Ozone Methylidynephosphane Potassium cyanide Trihydrogen cation Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water Four atoms Acetylene Ammonia Isocyanic 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 Propyne Methylamine Methyl isocyanate Vinyl alcohol Eight atoms Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Acrolein Nine atoms Acetamide Cyanohexatriyne Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Ethanethiol Propionitrile N-Methylformamide Ten atoms or more Acetone Benzene Benzonitrile Buckminsterfullerene (C60, C60, fullerene, buckyball) C70 fullerene Cyanodecapentayne Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Butyronitrile Pyrimidine Heptatrienyl radical
Deuterated molecules	Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Propyne N2D Trihydrogen cation
Unconfirmed	Anthracene Dihydroxyacetone Methoxyethane Glycine Graphene Hemolithin H2NCO Linear C5 Naphthalene cation Phosphine Pyrene Silylidyne
Related	Abiogenesis Astrobiology Astrochemistry Atomic and molecular astrophysics Chemical formula Circumstellar dust Circumstellar envelope Cosmic dust Cosmic ray Cosmochemistry Diffuse interstellar band Earliest known life forms Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism Homochirality Intergalactic dust Interplanetary medium Interstellar medium Photodissociation region Iron–sulfur world theory Kerogen Molecules in stars Nexus for Exoplanet System Science Organic compound Outer space PAH world hypothesis Pseudo-panspermia Polycyclic aromatic hydrocarbon (PAH) RNA world hypothesis Spectroscopy Tholin
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• Alkyne derivatives
• Conjugated nitriles