Norbornane

Norbornane
Names
Preferred IUPAC name
Bicyclo[2.2.1]heptane
Other names
norcamphane, norbornylane
Identifiers
3D model (JSmol)
1900379
ChEBI
ChemSpider
ECHA InfoCard 100.005.452 Edit this at Wikidata
EC Number
  • 205-996-2
UNII
  • InChI=1S/C7H12/c1-2-7-4-3-6(1)5-7/h6-7H,1-5H2 checkY
    Key: UMRZSTCPUPJPOJ-UHFFFAOYSA-N checkY
  • InChI=1/C7H12/c1-2-7-4-3-6(1)5-7/h6-7H,1-5H2
    Key: UMRZSTCPUPJPOJ-UHFFFAOYAR
  • C1CC2CCC1C2
Properties
C7H12
Molar mass 96.17 g mol−1
Appearance white volatile solid
Melting point 85 to 88 °C (185 to 190 °F; 358 to 361 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Norbornane (also known as bicyclo[2.2.1]heptane) is an organic compound and a saturated hydrocarbon with chemical formula C7H12. It is a crystalline compound with a melting point of 88 °C.[citation needed] The carbon skeleton is derived from cyclohexane ring with a methylene bridge in the 1,4- position, and is a bridged bicyclic compound. The compound is a prototype of a class of strained bicyclic hydrocarbons.

The compound was originally synthesized by reduction of norcamphor.

The name norbornane is derived from bornane, which is 1,7,7-trimethylnorbornane, being a derivative of camphor (bornanone). The prefix nor- refers to the stripping of the methyl groups from the parent molecule bornane.

See also

References

  1. ↑ Fort, Raymond C. Adamantane. Studies in Organic Chemistry. Vol. 5. New York, NY: Marcel Dekker. p. 123. Whereas noradamantane certainly is strained relative to, say, adamantane, it is the most stable of the tricyclononanes, being the only one that does not contain a bicyclo[2.2.1]heptane.
  2. ↑ Komppa, Gust.; Beckmann, Siegfried (1934). "Der Grundkörper der Camphergruppe, das Bicyclo-[1.2.2]-heptan, und die stereoisomeren Norborneole". Naturwissenschaften. 22: 171. doi:10.1007/BF01496254.