norbornane
{{chembox
| Watchedfields = changed
| verifiedrevid = 450425949
| ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageFile1 = NorbornaneNumbering.png
| 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 = C7H12
| MolarMass = 96.17 g mol−1
| Appearance = white volatile solid
| Density =
| MeltingPtC = 85 to 88
| BoilingPt =
| Solubility =
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|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
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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. 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.{{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 }}
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
- 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]