511404
5-Hexenenitrile
95%
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About This Item
Linear Formula:
H2C=CH(CH2)3CN
CAS Number:
Molecular Weight:
95.14
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
95%
InChI
1S/C6H9N/c1-2-3-4-5-6-7/h2H,1,3-5H2
SMILES string
C=CCCCC#N
InChI key
UNAQSRLBVVDYGP-UHFFFAOYSA-N
assay
95%
refractive index
n20/D 1.427 (lit.)
bp
165 °C (lit.)
density
0.837 g/mL at 25 °C (lit.)
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.
signalword
Warning
hcodes
Hazard Classifications
Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk
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
Regulatory Information
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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)
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)
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
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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