Cyclohexyne

Cyclohexyne
Names
	Preferred IUPAC name Cyclohexyne
Identifiers
CAS Number	1589-69-1;
3D model (JSmol)	Interactive image;
ChemSpider	9254522;
PubChem CID	11079373;
CompTox Dashboard (EPA)	DTXSID50454473;
	InChI InChI=1S/C6H8/c1-2-4-6-5-3-1/h1-4H2 Key: AAFFTDXPYADISO-UHFFFAOYSA-N;
	SMILES C1CCC#CC1;
Properties
Chemical formula	C6H8
Molar mass	80.130 g·mol−1
Density	0.9 g/cm³
Boiling point	100.1
Related compounds
Related compounds	Cyclobutyne; Cyclopentyne; Cyclooctyne; Cyclohexene; Cyclohexane; Cyclo(18)carbon
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyclohexyne is a highly reactive, strained cyclic alkyne with the molecular formula C₆H₈ and the structure of a six-membered carbon ring containing a triple bond.^[1] It is a member of the class of compounds known as arynes (or more broadly, cycloalkynes ) and is best classified as a six-membered cyclic alkyne . Due to its high ring strain and instability, cyclohexyne cannot be isolated under normal conditions and exists only as a short-lived reactive intermediate in certain organic reactions.^[2]

Synthesis

Cyclohexyne cannot be stored or isolated due to its extreme instability. It is generated in situ through the elimination of hydrogen halides from suitable precursors.^[3] Other methods include the use of organolithium reagents or photolytic or thermal activation of precursor molecules.^[4]

References

^ Parker, W. (31 October 2007). Alicyclic Chemistry: Volume 5. Royal Society of Chemistry. p. 248. ISBN 978-1-84755-548-9. Retrieved 29 July 2025.
^ Cava, M. P. (2 December 2012). Cyclobutadiene and Related Compounds. Elsevier. p. 17. ISBN 978-0-323-16312-5. Retrieved 29 July 2025.
^ Wiberg, Egon; Wiberg, Nils (2001). Inorganic Chemistry. Academic Press. p. 1613. ISBN 978-0-12-352651-9. Retrieved 29 July 2025.
^ Chari, Jason V.; Ippoliti, Francesca M.; Garg, Neil K. (15 March 2019). "Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors". The Journal of Organic Chemistry. 84 (6): 3652–3655. doi:10.1021/acs.joc.8b03223. ISSN 0022-3263. PMID 30840455. Retrieved 29 July 2025.

[1] Parker, W. (31 October 2007). Alicyclic Chemistry: Volume 5. Royal Society of Chemistry. p. 248. ISBN 978-1-84755-548-9. Retrieved 29 July 2025.

[2] Cava, M. P. (2 December 2012). Cyclobutadiene and Related Compounds. Elsevier. p. 17. ISBN 978-0-323-16312-5. Retrieved 29 July 2025.

[3] Wiberg, Egon; Wiberg, Nils (2001). Inorganic Chemistry. Academic Press. p. 1613. ISBN 978-0-12-352651-9. Retrieved 29 July 2025.

[4] Chari, Jason V.; Ippoliti, Francesca M.; Garg, Neil K. (15 March 2019). "Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors". The Journal of Organic Chemistry. 84 (6): 3652–3655. doi:10.1021/acs.joc.8b03223. ISSN 0022-3263. PMID 30840455. Retrieved 29 July 2025.

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