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
CAS Number	705-60-2 [1] N
3D model (JSmol)	Interactive image
ChemSpider	1266396 Y
ECHA InfoCard	100.155.731
PubChem CID	1549520
CompTox Dashboard (EPA)	DTXSID1041188
InChI InChI=1S/C9H9NO2/c1-8(10(11)12)7-9-5-3-2-4-6-9/h2-7H,1H3/b8-7+ Y Key: WGSVFWFSJDAYBM-BQYQJAHWSA-N Y InChI=1/C9H9NO2/c1-8(10(11)12)7-9-5-3-2-4-6-9/h2-7H,1H3/b8-7+ Key: WGSVFWFSJDAYBM-BQYQJAHWBX
SMILES [O-][N+](=O)/C(=C/c1ccccc1)C
Properties
Chemical formula	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EU classification (DSD) (outdated)	Harmful (Xn)
R-phrases (outdated)	R22, R36/37/38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).
N verify (what is YN ?)
Infobox references