Bornan

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Structural formula
Bornan's structural formula
General
Surname Bornan
other names
  • Camphane
  • Bornylan
  • 1,7,7-trimethylbicyclo [2.2.1] heptane
Molecular formula C 10 H 18
Brief description

"Six-sided tablet" [made of alcohol], "is characterized by its high volatility and great ability to sublimate"

External identifiers / databases
CAS number 464-15-3
PubChem 92108
ChemSpider 83155
DrugBank DB04501
Wikidata Q421333
properties
Molar mass 138.25 g mol −1
Physical state

firmly

Melting point

156-157 ° C

boiling point

161 ° C (757 Torr)

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

In organic chemistry, bornane is the name given to the bicyclic hydrocarbon that forms the basic structure of some terpenes . Important derivatives are the natural substances borneol and camphor . Because of the structural relationship to the latter, the hydrocarbon was also called camphane , but according to the IUPAC nomenclature rule A-72, this name (also “Bornylan”) should no longer be used.

nomenclature

The carbon atoms of the Bornane skeleton are numbered: The methyl group on C-1 (bridgehead) of the bicyclo [2.2.1] heptane skeleton bears the number 10. The geminal methyl groups on the "one-bridge" are numbered C-8 and C-9 numbered. The name camphane is misleading as an unsaturated hydrocarbon with a different structure is called camphene . So this would have to deliver camphane during the hydrogenation , but this is not the case.

Manufacturing

Bornane was obtained from bornyl chloride by reduction (dehalogenation), among other things with metallic sodium . The reduction of camphor, which was first reported by the discoverers of the Wolff-Kishner reduction , is likely to be more advantageous . In this case, the ketone was first used to produce the hydrazone , which was strongly heated with potassium hydroxide or sodium ethanolate. With the base potassium tert -butanolate in dimethyl sulfoxide, the reduction could be carried out at room temperature.

Individual evidence

  1. ↑ a b c d L. Wolff, Liebigs Ann. Chem. 394, 86 (1912)
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ Hans Beyer, Wolfgang Walter: Textbook of organic chemistry . 21st edition, S. Hirzel Verlag, Stuttgart 1988, p. 669, ISBN 3-7776-0438-0 .
  4. ↑ J. Kachler, FV Spitzer: Reports of the German Chemical Society 13, 615, 2236 (1880).
  5. ^ N. Kishner: Journal of the Russian Physico-Chemical Society 43, 582 (1911).
  6. ↑ DJ Cram, MRV Sayhun: J. Amer. Chem. Soc. 84, 1734 (1962).

Web links

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