Cyanoacetylene

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 an organic compound with the formula C ₃ H N 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]

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

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.
6. 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.