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Norbornane

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. 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.

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Norbornane
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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
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).
checkY verify (what is checkY☒N ?)

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. 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.1

The compound was originally synthesized by reduction of norcamphor.2

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

See also

References

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.
External links