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Sigma-Aldrich

4-Pentenenitrile

97%

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About This Item

Linear Formula:
CH2=CHCH2CH2CN
CAS Number:
592-51-8
Molecular Weight:
81.12
EC Number:
209-762-0
MDL number:
MFCD00151259
UNSPSC Code:
12352100
PubChem Substance ID:
24879303
NACRES:
NA.22

assay

97%

refractive index

n20/D 1.42 (lit.)

bp

140 °C (lit.)

density

0.814 g/mL at 25 °C (lit.)

SMILES string

C=CCCC#N

InChI

1S/C5H7N/c1-2-3-4-5-6/h2H,1,3-4H2

InChI key

CFEYBLWMNFZOPB-UHFFFAOYSA-N

General description

4-Pentenenitrile (4-PN) is a terminal alkene nitrile. It is obtained from 3-pentenenitrile via cationic nickel hydride or cobalt catalyzed isomerization. 4-Pentenenitrile undergoes hydrocyanation in the presence of bidentate nickel complexes (catalysts) to yield 3-pentenenitrile. 4-PN undergoes gas-phase reaction with OH radicals and Cl atoms in the presence of synthetic air and various reference compounds.

Application

4-Pentenenitrile may be used to synthesize 4-pentenylamine.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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B Ozierenski et al.
Die Nahrung, 37(1), 5-14 (1993-01-01)
The effects of 5-vinyloxazolidine-2-thione (VOT), 1-cyano-3-butene (CYB) and various isothiocyanates on parameters of hepatic phase I and phase II biotransformation were investigated in male rats after oral treatment for 3 consecutive days. The compounds with the exception of CYB caused
Ligand Descriptor Analysis in Nickel-Catalysed Hydrocyanation: A Combined Experimental and Theoretical Study.
Burello E, et al.
Advanced Synthesis & Catalysis, 347(6), 803-810 (2005)
Gas-phase reactivity study of (E)-3-pentenenitrile and 4-pentenenitrile towards OH radicals and Cl atoms at atmospheric pressure.
Colomer JP, et al.
Atmospheric Environment, 61, 597-604 (2012)
New methods for alkaloid synthesis: Generation of indole-2, 3-diquinomethanes as a route to indole alkaloids.
Gallagher T and Magnus P.
Tetrahedron, 37(23), 3889-3897 (1981)
Kinetic control in catalytic olefin isomerization. An explanation for the apparent contrathermodynamic isomerization of 3-pentenenitrile.
McKinney RJ.
Organometallics, 4(6), 1142-1143 (1985)
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