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.
Names | |
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IUPAC name
1-Phenyl-2-nitropropene | |
Other names
P2NP, β-methyl-β-nitropropene, (2-Nitro-1-propenyl)benzene | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.155.731 |
PubChem CID |
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CompTox Dashboard (EPA) |
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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 | |
EU classification (DSD) (outdated) |
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R-phrases (outdated) | R22, R36/37/38 |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). | |
Infobox references | |
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