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Chemical compound From Wikipedia, the free encyclopedia
β-Nitrostyrene is an aromatic compound and a nitroalkene used in the synthesis of indigo dye[1] and the slimicide bromo-nitrostyrene.[2]
Names | |
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Preferred IUPAC name
[(E)-2-Nitroethen-1-yl]benzene | |
Other names
β-Nitro-styrene, 2-Nitrovinylbenzene, 1-Nitro 2-Nitroethenylbenzene, ω-Nitrostyrene, γ-Nitrostyrene, trans-β-nitrostyrene, MFCD00007402 | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.002.788 |
EC Number |
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PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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Properties | |
C8H7NO2 | |
Molar mass | 149.149 g·mol−1 |
Appearance | Yellow crystalline solid |
Melting point | 58 °C (136 °F; 331 K) |
Boiling point | 255 °C (491 °F; 528 K) |
Hazards | |
Safety data sheet (SDS) | MSDS at Sigma Aldrich |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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β-Nitrostyrene is a chemical precursor for slimicides and dyes. Specifically bromo-nitrostyrene is obtained upon treatment with bromine followed by partial dehydrohalogenation[2] while 2-nitrobenzaldehyde is obtained by treatment with ozone respectively.[1]
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).[3]
The chemical is produced by either the Henry reaction of benzaldehyde and nitromethane[4][5] or by direct nitration of styrene using nitric oxide.[6]
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