15241-23-3

Basic information

• Product Name: [(Z)-2-Nitroethenyl]benzene
• Synonyms: (Z)-2-Nitroethenylbenzene;[(Z)-2-Nitroethenyl]benzene;(Z)-1-Phenyl-2-nitroethene;(Z)-2-Nitro-1-phenylethene;(Z)-β-Nitrostyrene;[(1Z)-2-Nitroethenyl]benzene;1-[(Z)-2-Nitrovinyl]benzene
• CAS NO: 15241-23-3
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 149.15
• Mol File: 15241-23-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 255.8 °C at 760 mmHg
• Flash Point: 117.5 °C
• Appearance: /
• Density: 1.177g/cm³
• Vapor Pressure: 0.0255mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: [(Z)-2-Nitroethenyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: [(Z)-2-Nitroethenyl]benzene(15241-23-3)
• EPA Substance Registry System: [(Z)-2-Nitroethenyl]benzene(15241-23-3)

Safety Data

• Hazardous Substances Data: 15241-23-3(Hazardous Substances Data)

Usage

General Description

[(Z)-2-Nitroethenyl]benzene, also known as beta-nitrostyrene, is an organic compound that consists of a benzene ring attached to a nitroethene group. It is a yellow crystalline solid that is used in the preparation of various organic compounds, particularly in the field of organic synthesis. It can be synthesized by the condensation reaction of benzaldehyde with nitroethane in the presence of a base and a catalyst. [(Z)-2-Nitroethenyl]benzene is known for its potential pharmacological activities and has been studied for its potential use in the development of pharmaceutical drugs. However, it is important to handle this chemical with caution as it is a potential irritant and can be harmful if ingested or inhaled.

InChI:InChI=1/C8H7NO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H

Upstream product

• 100-42-5 styrene 
• 5153-67-3 nitrostyrene 
• 543-75-9 1,4-dioxene 
• 271-89-6 1-benzofurane 
• 760-21-4 2-ethyl-1-butene 
• 17510-46-2 3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene 
• 766-90-5 cis-1-phenyl-1-propylene 
• 1192-37-6 methylenecyclohexane 
• 1191-99-7 2,3-dihydro-2H-furan 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 873-66-5 1-propenylbenzene 
• 100-52-7 benzaldehyde 
• 75-52-5 nitromethane 
• 7422-28-8 (Z)-1-Phenyl-2-(trimethylstannyl)aethen 

Downstream Products

• 6852-55-7 N-benzylidenepropylamine 
• 74401-25-5 exo-1-nitro-endo-2-phenyl-1,1a,2,2a-tetrahydro-7H-cyclobutindene 
• 110551-61-6 diprotonated β-nitrostyrene 
• 5153-67-3 nitrostyrene 
• 105441-95-0 1-Nitro-2-phenyl-3-(5-methoxycarbonyl-2-methyl-3-furyl)-2,3-dihydrobenzoindolizine 
• 128589-14-0 dimethyl 4-phenyl-2-propyl-3-butenylphosphonate 
• 128589-29-7 (4-Nitro-3-phenyl-butyl)-phosphonic acid diethyl ester 
• 128589-30-0 (2-Methyl-4-nitro-3-phenyl-butyl)-phosphonic acid dimethyl ester 
• 18869-27-7 (E)-(2-cyclohexylvinyl)benzene 

Relevant articles and documents

On the Steric Course of the Reaction of Enamines Derived from Open-Chain Aldehydes and Ketones with Nitro-olefins Yielding 2,3-Disubstituted 4-Nitroketones

The relative configuration of the nitro-ketone 12 obtained by the title reaction has been proved by a Baeyer-Villiger degradation and subsequent reduction to the amino-alcohol (+/-)-(u)-20, the relative configuration of which is identical with a sample prepared from 2-methyl-3-hydroxybutyrate of known configuration (Scheme 1).The stereochemical course of the title reaction is thus as predicted by our topological rule.It is assumed that the other nitro-ketones 13-18 described here are also formed by (lk)-combination of the trigonal centers of the educts (diastereoselectivity > 90percent, see Formulae and Fig. 1).It is not possible to reverse this relative topicity by employing (Z)-instead of (E)-components of the starting materials, due to the reversibility of the primary step of these Michael additions (Schemes 2 and 3, and Fig.2).

Visible light-mediated intermolecular [2 + 2] photocycloaddition of 1-aryl-2-nitroethenes and olefins

Despite the importance of cyclobutanes there are not many direct [2 + 2] photocycloaddition reactions which can be performed with visible light in the absence of a catalyst. A notable exception is the reaction of 1-aryl-2-nitroethenes and olefins which can be performed at a wavelength of λ = 419 nm or λ = 424 nm in CH2Cl2 as the solvent. In the present study, a total of 15 1-aryl-2-nitroethenes were found to undergo a [2 + 2] photocycloaddition with 2,3-dimethyl-2-butene (28-86% yield) and a set of 12 olefins was studied in their photocycloaddition to 1-phenyl-2-nitroethene (37-88% yield). All mechanistic results are in agreement with a triplet reaction pathway and with the intermediacy of a 1,4-diradical.

Light-Enabled Enantiodivergence: Stereospecific Reduction of Activated Alkenes Using a Single Organocatalyst Enantiomer

Light-enabled enantiodivergence is demonstrated in which the alkene substrate configuration is manipulated (E → Z) prior to organocatalytic reduction with a chiral thiourea and Hantzsch ester. This allows stereodivergent reduction to be regulated at the substrate level with high fidelity and mitigates the need for a second, enantiomeric catalyst (up to 93:07 and 95:5 er). The synthetic utility of this strategy has been demonstrated in the synthesis of the weight-loss drug (R)-Lorcaserin (Belviq) and a potent AMPA modulator.

Direct aziridination of nitroalkenes affording N-alkyl-C-nitroaziridines and the subsequent Lewis acid mediated isomerization to β-nitroenamines

A mild and highly diastereoselective one-pot synthesis of trans-N-alkyl-C-nitroaziridines was achieved by treatment of nitroalkenes with aliphatic amines and N-chlorosuccinimide. Treatment of the obtained aziridines with a Lewis acid resulted in a facile ring opening reaction, accompanied by rearrangement and isomerization into functionalized (Z)-β-nitroenamines.