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
ChemSpider	4447524
EC Number	203-066-0
Jmol interactive 3D	Image
PubChem	5284459
InChI InChI=1S/C9H10O3/c1-11-8-3-4-9(12-2)7(5-8)6-10/h3-6H,1-2H3 Key: PIAOLBVUVDXHHL-VOTSOKGWSA-N 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)
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

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

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]

See also

• Alkene
• Nitro compound

References

1. Wright, Elaine and Brühne, Friedrich (2000). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry: 8. doi:10.1002/14356007.a03_463. Retrieved 13 January 2014.
2. Markofsky, Sheldon B. (2000). "Nitro Compounds, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry: 6. doi:10.1002/14356007.a17_401. Retrieved 13 January 2014.
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; and 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.; and 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.