Cyclononyne
Chemical compound
From Wikipedia, the free encyclopedia
Cyclononyne is an organic compound with the chemical formula C9H14.[1] Its molecule has a ring of nine carbon atoms, connected by eight single bonds and one triple bond.[2]
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| Names | |
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| Preferred IUPAC name
Cyclononyne | |
| Identifiers | |
3D model (JSmol) |
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| 1920441 | |
| ChEBI | |
| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C9H14 | |
| Molar mass | 122.211 g·mol−1 |
| Density | 0.8972 g/cm³ |
| Boiling point | 68 °C (154 °F; 341 K) at 15 Torr |
| Related compounds | |
Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
The compound can be prepared by converting 1,2-cyclononanedione to the corresponding dihydrazone via hydrazine and then reacting it with mercuric oxide in the presence of sodium sulfate.[3][4] When 1,2-cyclononadiene is exposed to light in a dilute pentane solution, it will produce a small amount of cyclononyne and other C9 cycloolefin products via the intermediate isomer of bicyclo[6.1.0]non-8-ene.[5]
Properties
It is reported that pyrolysis of cyclononyne at 600 °C will lead to forming 1,2,8-nonatriene and trans-bicyclo[4.3.0]nona-2-ene in a 1:0.9 ratio.[6]
Under the catalysis of a rhodium complex, it is refluxed with sulfur in butanone to obtain a dithiol derivative, which is then refluxed in o-dichlorobenzene and desulfurized to obtain a thiophene derivative.[5]