Beta-Nitrostyrene Explained

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).[1]

Chemical synthesis

The chemical is produced by either the Henry reaction of benzaldehyde and nitromethane[2] [3] or by direct nitration of styrene using nitric oxide.[4]

Notes and References

  1. Book: Shulgin, Alexander . Pihkal : a chemical love story . Transform Press . Berkeley, CA . 1991 . 978-0-9630096-0-9 .
  2. Book: Furniss, Brian . Hannaford, Antony . Smith, Peter . Tatchell, Austin . amp . Vogel's Textbook of Practical Organic Chemistry 5th Ed.. 1996. Longman Science & Technical. London. 9780582462366. 1035.
  3. Worrall. David E.. Nitrostyrene. Org. Synth.. 1929. 9. 66. 13 January 2014. 10.15227/orgsyn.009.0066.
  4. Mukaiyama, T. . Hata E. . Yamada, T. . amp . Convenient and Simple Preparation of Nitroolefins Nitration of Olefins with Nitric Oxide. Chemistry Letters. 1995. 24. 7. 505–506. 10.1246/cl.1995.505. 5 January 2014.