Cyanoacetylene

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

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

H−C≡C−H + H−C≡N → H−C≡C−C≡N + H₂

Nickel carbonyl catalyzes cyanoacetylene carboalkoxylation to cyanoacrylate esters.^[6]

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