Bicyclo(1.1.1)pentane

The correct title of this article is Bicyclo[1.1.1]pentane. The substitution of any brackets is due to technical restrictions.

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.

bicyclo[1.1.1]pentane

Names
Preferred IUPAC name Bicyclo[1.1.1]pentane
Identifiers
CAS Number	311-75-1
3D model (JSmol)	Interactive image
ChemSpider	119929
PubChem CID	136153
CompTox Dashboard (EPA)	DTXSID60185044
InChI InChI=1S/C5H8/c1-4-2-5(1)3-4/h4-5H,1-3H2 Key: MKCBRYIXFFGIKN-UHFFFAOYSA-N
SMILES C1C2CC1C2
Properties
Chemical formula	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). Infobox references

Bicyclo[1.1.1]pentane is a highly strained molecule.

Usage

[1.1.1]Propellane

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]

The bicyclo[1.1.1]pentane structure has been used as an unusual bioisostere for a phenyl ring.^[3]

See also

• Housane
• Staffane