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  N
3D model (JSmol)	Interactive image
ChemSpider	1266396 Y
ECHA InfoCard	100.155.731
PubChem CID	1549520
CompTox Dashboard (EPA)	DTXSID601336391 DTXSID1041188, DTXSID601336391
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)
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

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. However, with lithium aluminium hydride it can simply be reduced to directly form amphetamine in moderate yields.

Synthesis of phenyl-2-nitropropene