3,7-dimethylocta-2,6-diene nitrile

Structural formula
Structural formula of the ( E ) isomer
General
Surname	3,7-dimethylocta-2,6-diene nitrile
other names	Geranyl nitrile Citronitrile
Molecular formula	C 10 H 15 N
Brief description	colorless to yellow liquid
External identifiers / databases
CAS number 5146-66-7 5585-39-7 [( E ) -form] 31983-27-4 [( Z ) -form] EC number 225-918-0 ECHA InfoCard 100,023,562 PubChem 21768 ChemSpider 20458 Wikidata Q2700125
properties
Molar mass	149.24 g mol −1
Physical state	liquid
density	0.853 g cm −3
Melting point	<−50 ° C
boiling point	260 ° C
Vapor pressure	3.7 Pa (20 ° C)
Refractive index	1.475 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 340-411 P: 201-273-308 + 313-391-405-501
Toxicological data	3100 mg kg −1 ( LD 50 ,  rat ,  oral ) 4300 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
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

3,7-Dimethylocta-2,6-diene nitrile is a chemical compound from the group of nitriles .

Extraction and presentation

3,7-Dimethylocta-2,6-diene nitrile can be obtained from citral ( 1 ) by reacting with hydroxylamine to citraloxime ( 2 ) and dehydrating it.

Furthermore, 3,7-dimethylocta-2,6-dienonitrile can be produced from 6-methyl-5-hepten-2-one ( 3 ) by Doebner's reaction with cyanoacetic acid ( 4 ) with dehydration and subsequent decarboxylation of intermediate 5 .

properties

3,7-Dimethylocta-2,6-diene nitrile is a colorless to yellow liquid.

use

3,7-Dimethylocta-2,6-diene nitrile has been used as an odorous substance since the 1940s .

Individual evidence

1. ↑ ^{a b c d e f g h i} Entry on 3,7-Dimethylocta-2,6-diennitrile in the GESTIS substance database of the IFA , accessed on February 5, 2019(JavaScript required) .
2. ↑ ^{a b c d e} D. LJ Opdyke: Monographs on Fragrance Raw Materials A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology . Elsevier, 2013, ISBN 978-1-4831-4797-0 , pp. 407 ( limited preview in Google Book search).
3. ↑ Data sheet 3,7-dimethyl-2,6-octadiene nitrile, mixture of isomers, ≥97% from Sigma-Aldrich , accessed on February 5, 2019 ( PDF ).
4. ↑ Entry on 3,7-dimethylocta-2,6-Dienitrile in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 6, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ^ Charles Sell: The Chemistry of Fragrances From Perfumer to Consumer . Royal Society of Chemistry, 2006, ISBN 978-0-85404-824-3 , pp. 67 ( limited preview in Google Book search).
6. ↑ ^{a b} Kirk-Othmer: Kirk-Othmer Chemical Technology of Cosmetics . John Wiley & Sons, 2012, ISBN 1-118-51890-X ( limited preview in Google Book Search).