Norbornane: Difference between revisions

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Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|error
 
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{{chembox
{{chembox
| Watchedfields = changed
| verifiedrevid = 439349846
| verifiedrevid = 450425949
| ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageFile1 = Norbornane-2D-skeletal.png
| ImageFile1 = NorbornaneNumbering.png
| ImageSize1 = 180px
| ImageSize1 = 180px
| ImageFile2 = Norbornane-3D-balls.png
| ImageFile2 = Norbornane-3D-balls.png
| ImageSize2 =
| ImageSize2 =
| ImageFile3 = Norbornan.gif
| IUPACName = norbornane
| ImageSize3 = 180px
| OtherNames = bicyclo[2.2.1]heptane
| PIN = Bicyclo[2.2.1]heptane
| Section1 = {{Chembox Identifiers
| OtherNames = norcamphane, norbornylane
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 279-23-2
| Beilstein = 1900379
| ChEBI = 71546
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8878
| 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
| InChI = 1/C7H12/c1-2-7-4-3-6(1)5-7/h6-7H,1-5H2
| InChIKey = UMRZSTCPUPJPOJ-UHFFFAOYAR
| InChIKey = UMRZSTCPUPJPOJ-UHFFFAOYAR
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UMRZSTCPUPJPOJ-UHFFFAOYSA-N
| StdInChIKey = UMRZSTCPUPJPOJ-UHFFFAOYSA-N
| CASNo = 279-23-2
| SMILES = C1CC2CCC1C2
| PubChem = 9233
| SMILES = C1CC2CCC1C2
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>7</sub>H<sub>12</sub>
| Formula = C<sub>7</sub>H<sub>12</sub>
| MolarMass = 96.17 g mol<sup>−1</sup>
| MolarMass = 96.17 g mol<sup>−1</sup>
| Appearance =
| Appearance = white volatile solid
| Density =
| Density =
| MeltingPtCL = 85
| MeltingPtC = 85 to 88
| MeltingPtCH = 88
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
}}
}}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition =
| AutoignitionPt =
}}
}}
}}
}}


'''Norbornane''' (also known as '''bicyclo[2.2.1]heptane''') is an [[organic compound]] and a [[saturated compound|saturated]] [[hydrocarbon]] with [[chemical formula]] C<sub>7</sub>H<sub>12</sub>. It is a [[crystalline]] compound with [[melting point]] 88 [[°C]]. The carbon skeleton is a [[cyclohexane]] ring bridged by a [[methylene]] group in the 1,4- position, and is a bridged [[bicyclic]] compound. The compound can be synthesized by [[hydrogenation]] of the related compounds [[norbornene]] and [[norbornadiene]]. The norbornyl cation (C<sub>7</sub>H<sub>11</sub><sup>+</sup>) is of great scientific interest in relation to [[non-classical ion]]s.
'''Norbornane''' (also known as '''bicyclo[2.2.1]heptane''') is an [[organic compound]] and a [[saturated compound|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]]. 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]].<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 compound got its name from [[bornane]] which has three methyl groups and is the carbon skeleton for [[camphor]] (bornanone). In bornane, there is one methyl group attached to a carbon at the base of the bridge and two methyl groups attached to the carbon at the apex of the bridge. The prefix ''nor'' refers to the stripping of the methyl groups from the original bornane.


The name norbornane is derived from [[bornane]], which is 1,7,7-trimethylnorbornane, being a derivative of [[camphor]] (bornanone). The prefix [[nor-|''nor'']] refers to the stripping of the methyl groups from the parent molecule bornane.
== External links ==
* [http://www-jmg.ch.cam.ac.uk/data/molecules/misc/norbornane.html Norbornane in 3D]
* [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/N32008 datasheet]


==See also==
[[Category:Hydrocarbons]]
* [[2-Norbornyl cation]]
* [[Norbornene]]
* [[Norbornadiene]]
* [[Bornane]]
* [[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]
* [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/N32008 Datasheet at ''Sigma-Aldrich'']


[[Category:Bicycloalkanes]]
[[de:Norbornan]]
[[Category:Norbornanes| ]]
[[es:Norbornano]]
[[it:Norbornano]]
[[hu:Norbornán]]
[[nl:Norbornaan]]
[[ja:ノルボルナン]]
[[pl:Norbornan]]
[[zh:降冰片烷]]