Norbornane

Norbornane
Names
	Preferred IUPAC name Bicyclo[2.2.1]heptane
	Other names norcamphane, norbornylane
Identifiers
CAS Number	279-23-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1900379
ChEBI	CHEBI:71546;
ChemSpider	8878 ;
ECHA InfoCard	100.005.452
EC Number	205-996-2;
PubChem CID	9233;
UNII	PAF9G8MY72 ;
CompTox Dashboard (EPA)	DTXSID4075376 ;
	InChI InChI=1S/C7H12/c1-2-7-4-3-6(1)5-7/h6-7H,1-5H2 Key: UMRZSTCPUPJPOJ-UHFFFAOYSA-N ; InChI=1/C7H12/c1-2-7-4-3-6(1)5-7/h6-7H,1-5H2 Key: UMRZSTCPUPJPOJ-UHFFFAOYAR;
	SMILES C1CC2CCC1C2;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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.^[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.

References

↑ 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.
↑ 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

Norbornane in 3D Archived 2011-05-14 at the Wayback Machine
Datasheet at Sigma-Aldrich

[Ad-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.

[1]

[2]

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Norbornane

See also

References

External links