Phenyl-2-nitropropene

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 the drug Adderall, an amphetamine mixture, which is used to treat ADHD and narcolepsy.

Synthesis of phenyl-2-nitropropene
1-Phenyl-2-nitropropene
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R-phrases (outdated) R22, R36/37/38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).
N verify (what is YN ?)
Infobox references

References


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