![]() | |
Names | |
---|---|
Preferred IUPAC name Cyclodecyne | |
Other names 1-Cyclodecyne | |
Identifiers | |
3D model (JSmol) | |
2203338 | |
ChEBI | |
ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C10H16 | |
Molar mass | 136.238 g·mol−1 |
Density | 0.898 g/cm³ |
Boiling point | 205 °C (401 °F; 478 K) |
Related compounds | |
Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Cyclodecyne is an organic compound with the chemical formula C10H16. [1] [2] The molecule has a ring of 10 carbon atoms, connected by nine single bonds and one triple bond. [3]
Cyclodecyne was first synthesized and isolated in the mid-20th century as part of studies on medium-ring hydrocarbons. A common synthetic route involves the double dehydrohalogenation of 1,2-dibromocyclodecane using a strong base such as potassium hydroxide (KOH) or sodium amide (NaNH2) in a high-boiling solvent [4] :
Alternatively, Fritsch–Buttenberg–Wiechell rearrangement of suitable dibromovinyl precursors has been used to generate cyclodecyne under milder conditions. [5]
Due to its reactivity, cyclodecyne is often generated in situ and trapped in cycloaddition reactions rather than stored for long periods.