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424595

Sigma-Aldrich

5-Nitro-1-pentene

98%

Linear Formula:
O2N(CH2)3CH=CH2
CAS Number:
Molecular Weight:
115.13
MDL number:
PubChem Substance ID:

assay

98%

form

liquid

refractive index

n20/D 1.44 (lit.)

bp

82 °C/32 mmHg (lit.)

density

1.007 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[O-][N+](=O)CCCC=C

InChI

1S/C5H9NO2/c1-2-3-4-5-6(7)8/h2H,1,3-5H2

InChI key

NPFOLTHIKZSVPQ-UHFFFAOYSA-N

Related Categories

General description

5-Nitro-1-pentene is a nitro alkene. It undergoes conjugate addition to 3-buten-2-one by C-C bond formation. Its enthalpy of vaporization at boiling point has been determined.

Application

5-Nitro-1-pentene was used as a substrate in the microwave assisted cross metathesis reaction with allyl trimethylsilane (allylTMS).
It may be used as a precursor for the preparation of allylrethrone and as a starting material in the synthesis of 3-(3′-butenyl)-5-acetyl-2-isoxazoline.

Certificate of Analysis

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Certificate of Origin

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5-Nitro-1-pentene as a precursor for the synthesis of allylrethrone.
Ballini R.
Synthesis, 7, 687-688 (1993)
Reluctant cross-metathesis reactions: the highly beneficial effect of microwave irradiation.
Michaut A, et al.
Synthesis, 18, 2867-2871 (2007)
Yaws CL.
Thermophysical Properties of Chemicals and Hydrocarbons, 430-430 (2008)
Silyl nitronates in organic synthesis. Routes to heterocycles and cyclopentanoids. Synthesis of allethrolone and calythrone. Acylation and cyanohydroxylation of double bonds. An exploratory study.
Knudsen J, et al.
Acta Chemica Scandinavica. Series B, 36, 1-14 (1982)

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