Phenyl-2-nitropropene

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1-Phenyl-2-nitropropene
Phenyl-2-nitropropene.svg
Names
IUPAC name
1-Phenyl-2-nitropropene
Other names
P2NP, β-methyl-β-nitropropene, (2-Nitro-1-propenyl)benzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.155.731
Properties
C9H9NO2
Molar mass 163.17 g mol−1
Appearance solid
Melting point 64 to 66 °C (147 to 151 °F; 337 to 339 K)
Hazards
Harmful (Xn)
R-phrases (outdated) R22, R36/37/38
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Phenyl-2-nitropropene is a chemical compound with the chemical formula is C9H9NO2. It can be produced by the reaction of benzaldehyde and nitroethane in the presence of a basic catalyst. In this reaction, the base deprotonates nitroethane to form a resonance stabilized anion. This anion nucleophilically adds to the aldehyde forming a beta nitro alcohol, which is subsequently dehydrated to yield the nitroalkene. This reaction is known as a nitroaldol reaction. Phenyl-2-nitropropene is used to make pharmaceuticals. It is used in pharmaceutical industry to manufacture drug Adderall, an amphetamine mixture, which is used to treat ADHD and narcolepsy.

Synthesis of phenyl-2-nitropropene

References[edit]

  1. ^ Alfa MSDS Archived 2007-09-27 at the Wayback Machine.