β-Nitrostyrene

β-Nitrostyrene
Names
	Preferred IUPAC name [(E)-2-Nitroethen-1-yl]benzene
	Other names (2-Nitrovinyl)benzene; (2-Nitroethenyl)benzene; ω-Nitrostyrene; 1-Nitro-2-phenylethene; 1-Nitro-2-phenylethylene
Identifiers
CAS Number	102-96-5; ;
3D model (JSmol)	Interactive image;
ChemSpider	4447524 ;
ECHA InfoCard	100.002.788
EC Number	203-066-0;
PubChem CID	5284459;
UNII	[https://precision.fda.gov/uniisearch/srs/unii/5287E3OUAV 5153-67-3 (trans) 5287E3OUAV 5153-67-3 (trans)] ;
CompTox Dashboard (EPA)	DTXSID0025789 ;
	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	149.149 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). verify (what is ?) 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]

Related compounds

3-Nitrostyrene (O₂NC₆H₄CH=CH₂)^[7]

References

^ ^a ^b Wright, Elaine & Brühne, Friedrich (2000). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 8. doi:10.1002/14356007.a03_463. ISBN 978-3527306732.
^ ^a ^b Markofsky, Sheldon B. (2000). "Nitro Compounds, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 6. doi:10.1002/14356007.a17_401. ISBN 978-3527306732.
^ Shulgin, Alexander (1991). Pihkal : a chemical love story. Berkeley, CA: Transform Press. ISBN 978-0-9630096-0-9.
^ 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.
^ Worrall, David E. (1929). "Nitrostyrene" (PDF). Org. Synth. 9: 66. doi:10.15227/orgsyn.009.0066. Retrieved 13 January 2014.
^ 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.
^ Wiley, Richard H.; Smith, Newton R. (1953). "m-Nitrostyrene". Organic Syntheses. 33: 62. doi:10.15227/orgsyn.033.0062.

[indigo-1] Wright, Elaine & Brühne, Friedrich (2000). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 8. doi:10.1002/14356007.a03_463. ISBN 978-3527306732.

[slimicide-2] Markofsky, Sheldon B. (2000). "Nitro Compounds, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 6. doi:10.1002/14356007.a17_401. ISBN 978-3527306732.

[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.

[7] Wiley, Richard H.; Smith, Newton R. (1953). "m-Nitrostyrene". Organic Syntheses. 33: 62. doi:10.15227/orgsyn.033.0062.

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