Β-Nitrostyrene
{{lowercase title}}
{{Chembox
| Name = β-Nitrostyrene
| verifiedrevid = 401764526
| ImageFile = Beta-nitrostyrene.svg
| ImageSize = 200
| ImageAlt1 = Beta-Nitrostyrene molecule
| PIN = [(E)-2-Nitroethen-1-yl]benzene
| OtherNames = (2-Nitrovinyl)benzene
(2-Nitroethenyl)benzene
ω-Nitrostyrene
1-Nitro-2-phenylethene
1-Nitro-2-phenylethylene
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4447524
| InChIKey = AFUKNJHPZAVHGQ-UHFFFAOYAN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H10O3/c1-11-8-3-4-9(12-2)7(5-8)6-10/h3-6H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PIAOLBVUVDXHHL-VOTSOKGWSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 102-96-5; 5153-67-3 (trans)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5287E3OUAV
| EINECS = 203-066-0
| PubChem = 5284459
| SMILES = C1=CC=C(C=C1)/C=C/[N+](=O)[O-]
| InChI = InChI=1S/C8H7NO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H/b7-6+
}}
| Section2 = {{Chembox Properties
| Formula = | C=8 | H=7 | N=1 | O=2
| Appearance = Yellow crystalline solid
| MeltingPtC = 58
| BoilingPtC = 255
}}
| Section3 = {{Chembox Hazards
| ExternalSDS = [https://www.sigmaaldrich.com/US/en/sds/aldrich/n26806 MSDS at Sigma Aldrich]
}}
}}
β-Nitrostyrene is an aromatic compound and a nitroalkene used in the synthesis of the slimicide bromo-nitrostyrene.{{Ullmann|last=Markofsky|first=Sheldon B.|title=Nitro Compounds, Aliphatic|year=2000|page=6|doi=10.1002/14356007.a17_401}}
Applications
β-Nitrostyrene is a chemical precursor for slimicides and dyes. Specifically bromo-nitrostyrene is obtained upon treatment with bromine followed by partial dehydrohalogenation.
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).{{cite book | last = Shulgin | first = Alexander | title = Pihkal : a chemical love story | publisher = Transform Press | location = Berkeley, CA | year = 1991 | isbn = 978-0-9630096-0-9 }}
Chemical synthesis
The chemical is produced by either the Henry reaction of benzaldehyde and nitromethane{{cite book|author1=Furniss, Brian |author2=Hannaford, Antony |author3=Smith, Peter |author4=Tatchell, Austin |name-list-style=amp |title=Vogel's Textbook of Practical Organic Chemistry 5th Ed.|year=1996|publisher=Longman Science & Technical|location=London|isbn=9780582462366|page=[https://archive.org/details/TextbookOfPracticalOrganicChemistry5thEd/page/n1059 1035]|url=https://archive.org/details/TextbookOfPracticalOrganicChemistry5thEd}}{{cite journal|last=Worrall|first=David E.|title=Nitrostyrene|journal=Org. Synth.|year=1929|volume=9|pages=66|url=http://www.orgsyn.org/Content/pdfs/procedures/cv1p0413.pdf|accessdate=13 January 2014|doi=10.15227/orgsyn.009.0066}} or by direct nitration of styrene using nitric oxide.{{cite journal|author1=Mukaiyama, T. |author2=Hata E. |author3=Yamada, T. |name-list-style=amp |title=Convenient and Simple Preparation of Nitroolefins Nitration of Olefins with Nitric Oxide|journal=Chemistry Letters|year=1995|volume=24|issue=7|pages=505–506|doi=10.1246/cl.1995.505|url=https://www.jstage.jst.go.jp/article/cl/24/7/24_7_505/_article|accessdate=5 January 2014|url-access=subscription}}
Related compounds
References
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{{DEFAULTSORT:Nitrostyrene, β-}}