Phenyl-2-nitropropene

1-Phenyl-2-nitropropene
IUPAC name 1-Phenyl-2-nitropropene
Other names P2NP, β-methyl-β-nitropropene, (2-Nitro-1-propenyl)benzene
Identifiers
CAS number	705-60-2 N, [1]
PubChem	1549520
ChemSpider	1266396 Y
Jmol-3D images	{{#if:[O-][N+](=O)/C(=C/c1ccccc1)C|Image 1
SMILES [O-][N+](=O)/C(=C/c1ccccc1)C
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
Properties
Molecular formula	C9H9NO2
Molar mass	163.17 g mol−1
Appearance	solid
Melting point	64-66 °C
Hazards
EU classification	Harmful (Xn)
R-phrases	R22, R36/37/38
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 can be reduced in the presence of a catalyst to produce phenylacetone, which is a controlled precursor of methamphetamine. With lithium aluminium hydride, it can be reduced to amphetamine.

References