beta-Nitrostyrene

β-Nitrostyrene

Names
IUPAC name 2-Nitrovinylbenzene
Other names β-Nitro-styrene, 2-Nitrovinylbenzene, 1-Nitro-2-phenylethylene, 2-Nitroethenylbenzene, ω-Nitrostyrene, γ-Nitrostyrene, trans-β-nitrostyrene, MFCD00007402
Identifiers
CAS Number	102-96-5 Y
ChemSpider	4447524 Y
EC Number	203-066-0
Jmol 3D model	Interactive image
PubChem	5284459
InChI InChI=1S/C9H10O3/c1-11-8-3-4-9(12-2)7(5-8)6-10/h3-6H,1-2H3 Y Key: PIAOLBVUVDXHHL-VOTSOKGWSA-N Y InChI=1S/C8H7NO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H/b7-6+ Key: AFUKNJHPZAVHGQ-UHFFFAOYAN
SMILES C1=CC=C(C=C1)/C=C/[N+](=O)[O-]
Properties
Chemical formula	C8H7NO2
Molar mass	149.15 g·mol−1
Appearance	Yellow crystalline solid
Melting point	58 °C (136 °F; 331 K)
Boiling point	255 °C (491 °F; 528 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

β-Nitrostyrene is an aromatic compound and a nitroalkene used in the synthesis of indigo dye and the slimicide bromo-nitrostyrene.

Applications

β-Nitrostyrene is a chemical precursor for slimicides and dyes. Specifically bromo-nitrostyrene is obtained upon treatment with bromine followed by partial dehydrohalogenation while 2-nitrobenzaldehyde is obtained by treatment with ozone respectively.

Many of the syntheses of psychedelic substituted phenethylamines and substituted amphetamines described by Alexander Shulgin in his book PiHKAL use substituted nitrostyrenes as precursors. They are the final precursor, reduced with lithium aluminium hydride to the final product (an amine).

Chemical synthesis

The chemical is produced by either the Henry reaction of benzaldehyde and nitromethane or by direct nitration of styrene using nitric oxide.

See also

• Alkene
• Nitro compound