Bicyclo(1.1.1)pentane
Chemical compound
From Wikipedia, the free encyclopedia
Bicyclo[1.1.1]pentane is an organic compound, the simplest member of the bicyclic bridged compounds family. It is a hydrocarbon with formula C5H8. The molecular structure consists of three rings of four carbon atoms each.
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| Preferred IUPAC name
Bicyclo[1.1.1]pentane | |||
| Identifiers | |||
3D model (JSmol) |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |||
| C5H8 | |||
| Molar mass | 68.119 g·mol−1 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bicyclo[1.1.1]pentane is a highly strained molecule.
Usage
Kenneth Wiberg and Frederick Walker used a bicyclo[1.1.1]pentane derivative to make [1.1.1]propellane.[1] Conversely, some substituted bicyclo[1.1.1]pentanes are best synthesized from the corresponding propellanes.[2][3]
The bicyclo[1.1.1]pentane structure has been used as an unusual bioisostere for a phenyl ring.[4]