{{chembox | Watchedfields = changed | verifiedrevid = 450425949 | ImageFile1_Ref = {{chemboximage|correct|??}} | ImageFile1 = NorbornaneNumbering.svg | ImageSize1 = 180px | ImageFile2 = Norbornane-3D-balls.png | ImageSize2 = | ImageFile3 = Norbornane-spin.gif | ImageSize3 = 180px | PIN = Bicyclo[2.2.1]heptane | OtherNames = norcamphane, norbornylane |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 279-23-2 | Beilstein = 1900379 | ChEBI = 71546 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8878 | EINECS = 205-996-2 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = PAF9G8MY72 | PubChem = 9233 | InChI = 1/C7H12/c1-2-7-4-3-6(1)5-7/h6-7H,1-5H2 | InChIKey = UMRZSTCPUPJPOJ-UHFFFAOYAR | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C7H12/c1-2-7-4-3-6(1)5-7/h6-7H,1-5H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = UMRZSTCPUPJPOJ-UHFFFAOYSA-N | SMILES = C1CC2CCC1C2 }} |Section2={{Chembox Properties | Formula = C<sub>7</sub>H<sub>12</sub> | MolarMass = 96.17 g mol<sup>−1</sup> | Appearance = white volatile solid | Density = | MeltingPtC = 85 to 88 | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Norbornane''' (also known as '''bicyclo[2.2.1]heptane''') is an organic compound and a saturated hydrocarbon with chemical formula C<sub>7</sub>H<sub>12</sub>. It is a crystalline compound with a melting point of 88 °C.{{cn|date=January 2026}} 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.<ref name=Ad>{{cite book|series=Studies in Organic Chemistry|volume=5|title=Adamantane|first=Raymond C.|last=Fort|publisher=Marcel Dekker|location=New York, NY|p=123|quote=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.}}</ref>
The compound was originally synthesized by reduction of norcamphor.<ref>{{cite journal |last=Komppa |first=Gust. |last2=Beckmann |first2=Siegfried |title=Der Grundkörper der Camphergruppe, das Bicyclo-[1.2.2]-heptan, und die stereoisomeren Norborneole |journal=Naturwissenschaften |year=1934 |volume=22 |pages=171 |doi=10.1007/BF01496254 }}</ref>
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== * 2-Norbornyl cation * Norbornene * Norbornadiene * endo-Norborneol * exo-Norborneol * Norcamphor, the ketone derivative of norbornane
==References== {{Reflist}}
==External links== * [http://www-jmg.ch.cam.ac.uk/data/molecules/misc/norbornane.html Norbornane in 3D] {{Webarchive|url=https://web.archive.org/web/20110514083612/http://www-jmg.ch.cam.ac.uk/data/molecules/misc/norbornane.html |date=2011-05-14 }} * [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/N32008 Datasheet at ''Sigma-Aldrich'']
Category:Bicycloalkanes Category:Norbornanes