Norbornane

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Structural formula
Structural formula of norbornane
General
Surname Norbornane
other names
  • Bicyclo [2.2.1] heptane ( IUPAC )
  • 8,9,10-trinorbornane
  • 1,4-endomethylene cyclohexane
  • Norbornylan
  • Norcamphan
  • Norfenchan
  • Norsantan
Molecular formula C 7 H 12
External identifiers / databases
CAS number 279-23-2
EC number 205-996-2
ECHA InfoCard 100.005.452
PubChem 9233
ChemSpider 8878
Wikidata Q418111
properties
Molar mass 96.17 g mol −1
Physical state

firmly

Melting point

85-88 ° C

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

56 mg kg −1 ( LD 50 ,  mouse ,  iv )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Norbornane (systematically: bicyclo [2.2.1] heptane ) is an organic compound , a saturated hydrocarbon with the empirical formula C 7 H 12 . At room temperature it is a crystalline solid. Structurally, it is a cyclohexane ring with a methylene bridge .

properties

An interesting property of this compound is its ability to form norbornyl carbonium ions - five-bonded carbocations of alkanes - by taking up a proton with a superacid . Since the 1950s there had been a decade-long dispute between Saul Winstein (non-classical character) and his critic Herbert C. Brown about the non-classical character of the 2-norbornyl cation , until the non-classical character was finally proven experimentally.

Non-classical (A) and classical (B) view of the 2-norbornyl cation

Related bicyclic compounds are norbornene , which has the same carbon structure but one double bond , and norbornadiene , also with the same structure but two double bonds and thus a diene .

use

Some norbornane derivatives are used as intermediates in the pharmaceutical industry, e.g. B. Camphor oxime .

See also

The synthesis of a saturated C 11 H 16 hydrocarbon called trinorbornane , which contains three norbornane structural elements, was published in 2017.

Individual evidence

  1. ↑ a b c d data sheet norbornane from Sigma-Aldrich , accessed on June 14, 2011 ( PDF ).Template: Sigma-Aldrich / name not given
  2. ↑ Observation of 2-norbornyl carbonium
  3. ↑ Mark Peplow: The nonclassical cation: a classic case of conflict Chemistry World, July, 20, 2013.
  4. ↑ Lorenzo Delarue Bizzini, Thomas Müntener, Daniel Häussinger, Markus Neuburger, Marcel Mayor: Synthesis of trinorbornane . In: Chem. Commun. tape 53 , no. 83 , 2017, p. 11399 , doi : 10.1039 / c7cc06273g ( unibas.ch [PDF]).

Web links

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