Camphene

Structural formula
	(+) - or D- camphene (left) and (-) - or L- camphene (right)
General
Surname	Camphene
other names	2,2-dimethyl-3-methylene-norbornane; 2,2-dimethyl-3-methylene-bicyclo [2.2.1] heptane;
Molecular formula	C 10 H 16
Brief description	colorless, cubic crystals with a turpentine odor
External identifiers / databases
EC number	201-234-8
ECHA InfoCard	100.001.123
PubChem	6616
ChemSpider	6364
Wikidata	Q416775
properties
Molar mass	136.23 g mol −1
Physical state	firmly
density	0.87 g · cm -3 (20 ° C)
Melting point	52 ° C [( R ) -Camphene] or [( S ) -Camphene] ; 51–52 ° C [( RS ) camphene] ;
boiling point	158-159 ° C
Vapor pressure	21.5 h Pa (50 ° C)
solubility	almost insoluble in water (4.2 mg l −1 at 20 ° C); moderate in ethanol , good in chloroform ;
Refractive index	1.5441 (54 ° C)
safety instructions
H and P phrases	H: 228-319-410
	P: 210-262-273-305 + 351 + 338
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Camphene (stress on the final syllable: Camph e n ) is a white, waxy solid. It is a bicyclic monoterpene - hydrocarbon , which molecular formula is C ₁₀ H ₁₆ . It comes as a racemate of the two enantiomers , D - and L -Camphen before.

Manufacturing

(-) - Camphene can be formed by rearrangement of the bornyl cation, which is formed by protonation and elimination of water from (-) - borneol .

properties

Camphene is almost insoluble in water; it is readily soluble in cyclohexane , alcohol and chloroform . The flash point of the racemate is 39 ° C.

use

Camphene is an intermediate product for the synthesis of flavors and smells. It is also needed for the production of camphor , stroban and toxaphene . It is part of the essential oil of the cubeb pepper .

Rod model of (+) - camphene

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on camphene in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
^ ^A ^b The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals. 9th edition. Merck & Co., Inc., Whitehouse Station, NJ, USA 1976, ISBN 0-911910-26-3 , p. 219.
↑ ^a ^b entry on camphene. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
^ Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta , Zurich, 2006, p. 206, ISBN 978-3-906390-29-1 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on camphene in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[MERCK_Index-2] A ^b The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals. 9th edition. Merck & Co., Inc., Whitehouse Station, NJ, USA 1976, ISBN 0-911910-26-3 , p. 219.

[roempp-3] try on camphene. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.

[Gossauer-4] Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta , Zurich, 2006, p. 206, ISBN 978-3-906390-29-1 .