beta-Nitrostyrene

β-Nitrostyrene is an aromatic compound and a nitroalkene used in the synthesis of indigo dye[1] and the slimicide bromo-nitrostyrene.[2]

β-Nitrostyrene
Names
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)
ChemSpider
ECHA InfoCard 100.002.788
EC Number
  • 203-066-0
UNII
  • InChI=1S/C9H10O3/c1-11-8-3-4-9(12-2)7(5-8)6-10/h3-6H,1-2H3 checkY
    Key: PIAOLBVUVDXHHL-VOTSOKGWSA-N checkY
  • InChI=1S/C8H7NO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H/b7-6+
    Key: AFUKNJHPZAVHGQ-UHFFFAOYAN
  • C1=CC=C(C=C1)/C=C/[N+](=O)[O-]
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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Infobox references

Applications

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]

Chemical synthesis

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]

References
  1. Wright, Elaine & Brühne, Friedrich (2000). Benzaldehyde. p. 8. doi:10.1002/14356007.a03_463. ISBN 978-3527306732. {{cite book}}: |journal= ignored (help)
  2. Markofsky, Sheldon B. (2000). "Nitro Compounds, Aliphatic". p. 6. doi:10.1002/14356007.a17_401. ISBN 978-3527306732. {{cite book}}: |journal= ignored (help); Missing or empty |title= (help)
  3. Shulgin, Alexander (1991). Pihkal : a chemical love story. Berkeley, CA: Transform Press. ISBN 978-0-9630096-0-9.
  4. Furniss, Brian; Hannaford, Antony; Smith, Peter & Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed. London: Longman Science & Technical. p. 1035. ISBN 9780582462366.
  5. Worrall, David E. (1929). "Nitrostyrene" (PDF). Org. Synth. 9: 66. doi:10.15227/orgsyn.009.0066. Retrieved 13 January 2014.
  6. Mukaiyama, T.; Hata E. & Yamada, T. (1995). "Convenient and Simple Preparation of Nitroolefins Nitration of Olefins with Nitric Oxide". Chemistry Letters. 24 (7): 505–506. doi:10.1246/cl.1995.505. Retrieved 5 January 2014.
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