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Sigma-Aldrich

5-Hexenenitrile

95%

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About This Item

Linear Formula:
H2C=CH(CH2)3CN
CAS Number:
5048-19-1
Molecular Weight:
95.14
MDL number:
MFCD00067056
UNSPSC Code:
12352100
PubChem Substance ID:
24873444
NACRES:
NA.22

assay

95%

refractive index

n20/D 1.427 (lit.)

bp

165 °C (lit.)

density

0.837 g/mL at 25 °C (lit.)

SMILES string

C=CCCCC#N

InChI

1S/C6H9N/c1-2-3-4-5-6-7/h2H,1,3-5H2

InChI key

UNAQSRLBVVDYGP-UHFFFAOYSA-N

General description

5-Hexenenitrile, an aliphatic nitrile, is a volatile compound that is formed as a degradation product of glucobrassicanapin in Aurinia sinuata. It is reported to be an attractant from oilseed rape for the cabbage seed weevil, Ceutorhynchus assimilis. 5-Hexenenitrile is the main volatile compound found in wheat extract. It undergoes Wacker oxidation to form the corresponding methyl ketone using PdCl2-DMA (palladium dichloride-N,N-diemthylacetamide) catalytic system.

Application

5-Hexenenitrile may be used in the synthesis of 1,8-dicyano-4-octene.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

104.9 °F - closed cup

flash_point_c

40.5 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Composition of the young green barley and wheat leaves.
Shibamoto T, et al.
J. Essent. Oil Res., 19(2), 134-137 (2007)
Convenient and Efficient Pd-Catalyzed Regioselective Oxyfunctionalization of Terminal Olefins by Using Molecular Oxygen as Sole Reoxidant.
Mitsudome T, et al.
Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 118(3), 495-499 (2006)
Shengxiang Ji et al.
Polymer, 49(24), 5307-5313 (2009-11-13)
High molecular weight, high functionality diamino telechelic polybutadienes (TPBs) were synthesized by ring-opening metathesis polymerization (ROMP) of 1,5-cyclooctadiene (COD) in the presence of a chain transfer agent, 1,8-dicyano-4-octene, followed by lithium aluminum hydride reduction. Melt coupling of diamino TPB with
The responses of the cabbage seed weevil Ceutorhynchus assimilis to volatile compounds from oilseed rape in a linear track olfactometer.
Bartlet E, et al.
Entomologia Experimentalis et Applicata, 85(3), 257-262 (1997)
Glucosinolates, glycosidically bound volatiles and antimicrobial activity of Aurinia sinuata (Brassicaceae).
Blazevic I, et al.
Food Chemistry, 121(4), 1020-1028 (2010)
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