4231-16-7

Basic information

• Product Name: 1-nitro-4-[(1E)-2-nitroprop-1-en-1-yl]benzene
• Synonyms: 1-Nitro-4-(2-nitro-1-propenyl)benzene; 1-Nitro-4-[(1E)-2-nitro-1-propen-1-yl]benzene; benzene, 1-nitro-4-[(1E)-2-nitro-1-propen-1-yl]-
• CAS NO: 4231-16-7
• Molecular Formula: C₉H₈N₂O₄
• Molecular Weight: 208.1708
• Mol File: 4231-16-7.mol

Chemical Properties

• Boiling Point: 323.9°C at 760 mmHg
• Flash Point: 152.9°C
• Density: 1.344g/cm³
• Vapor Pressure: 0.00048mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 1-nitro-4-[(1E)-2-nitroprop-1-en-1-yl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-nitro-4-[(1E)-2-nitroprop-1-en-1-yl]benzene(4231-16-7)
• EPA Substance Registry System: 1-nitro-4-[(1E)-2-nitroprop-1-en-1-yl]benzene(4231-16-7)

Safety Data

• Hazardous Substances Data: 4231-16-7(Hazardous Substances Data)

Usage

Benzene ring

One
A six-membered, unsaturated carbon ring with delocalized electrons, which provides the compound with stability and aromaticity.

Nitro groups

Two
Functional groups consisting of an oxygen and nitrogen atom (-NO2) attached to the benzene ring, contributing to the compound's reactivity and properties.

1-nitroprop-1-en-1-yl group

One
A functional group with a nitro (-NO2) attached to a propene (a three-carbon chain with a double bond) and an additional single bond to the benzene ring.

Uses

Intermediate in the synthesis of pharmaceuticals, dyes, and other organic compounds
The compound serves as a building block or precursor in the production of various pharmaceuticals, dyes, and other organic compounds.

Applications

Production of plasticizers and polymer resins
1,4-dinitrostyrene is used in the manufacturing of plasticizers (chemicals that increase the flexibility of plastics) and polymer resins (a base material for plastics and coatings).

Toxicity

Toxic
The compound is harmful and can cause adverse health effects if ingested, inhaled, or absorbed through the skin.

Hazards

Skin, eye, and respiratory system irritation
Exposure to 1,4-dinitrostyrene can cause irritation to the skin, eyes, and respiratory system, necessitating proper handling and safety precautions.

Upstream product

• 79-24-3 Nitroethane 
• 555-16-8 4-nitrobenzaldehdye 
• 142839-98-3 2-nitro-1-(4-nitrophenyl)propan-1-ol 
• 142840-00-4 Acetic acid 2-nitro-1-(4-nitro-phenyl)-propyl ester 
• 135711-51-2 Butyl-[2-nitro-1-(4-nitro-phenyl)-propyl]-amine 

Downstream Products

• 53359-85-6 tetraethyl 2-(4-nitrophenyl)ethene-1,1-diyldiphosphonate 
• 51146-36-2 aci-nitroethane trimethylsilyl ester 
• 99290-08-1 [(4S,5S)-3-Methyl-4-(4-nitro-phenyl)-2-oxy-4,5-dihydro-isoxazol-5-yl]-phenyl-methanone 
• 93530-63-3 N-hydroxy-p-nitroamphetamine 
• 1723-25-7 ethyl 2,3-dioxobutyrate 
• 95838-64-5 2,5-Dimethyl-4-(4-nitrophenyl)-3-pyrrolcarbonsaeure-ethylester 
• 95863-85-7 2-Acetyl-4-aci-nitro-3-(4-nitrophenyl)pentansaeure-ethylester 
• 62044-15-9 1-(4-amino-phenyl)propan-2-one 
• 29865-60-9 1-nitro-4-(2-nitropropyl)benzene 
• 109703-99-3 <5-Methyl-2-phenyl-4-(4-nitrophenyl)-3-pyrrolyl>phenylketon 
• 1210053-76-1 C₁₃H₁₃N₃O₄ 
• 1600521-09-2 1-(2,5-dimethyl-4-(4-nitrophenyl)-1-phenyl-1H-pyrrol-3-yl)ethanone 
• 25798-60-1 (1-nitro-4-(prop-1-en-1-yl)benzene) 

Relevant articles and documents

Synthesis and characterization of silica-polymer nanocomposites functionalized with piperazine for the synthesis of β-nitro alcohols

In order to compare the activity and selectivity for the synthesis of β-nitro alcohols, piperazine was functionalized directly and after surface modification into the ordered mesoporous SBA-15 framework. The materials were characterized by powder X-ray di

Ambiphilic dual activation role of a task-specific ionic liquid: 2-hydroxyethylammonium formate as a recyclable promoter and medium for the green synthesis of β-nitrostyrenes

A cost-effective task-specific ionic liquid, 2-hydroxyethylammonium formate, efficiently promotes the condensation of nitroalkanes with various aldehydes to produce β-nitrostyrenes in high to excellent yields at room temperature. This reaction does not involve any hazardous organic solvent and toxic catalyst. The ionic liquid is recovered and recycled for subsequent reactions. In addition, a novel mechanism has been proposed invoking ambiphilic dual activation influence of the ionic liquid.

Switchable perfomance of an L-proline-derived basic catalyst controlled by supramolecular gelation

An L-proline-derived low molecular weight gelator forms gels in nitromethane and nitroethane and acts as a basic catalyst for the Henry nitroaldol reaction of these solvents with 4-nitrobenzaldehyde and 4-chlorobenzaldehyde. The reported catalyst is effic

Spin trapping of alkoxyl radicals generated from 5-methyl and 5-aryl-3-alkoxy-4-methylthiazole-2(3H)-thiones in photochemically induced and microwave-initiated reactions

Methoxyl and isopropoxyl radicals were generated from N-alkoxy-4,5-dimethylthiazole-2(3H)-thiones (λmax～320 nm) and 5-aryl derivatives (aryl=p-XC6H4; X=MeO, H, AcNH, Cl) (λmax～335 nm) in photochemically and microwave-induced reactions. Alkoxyl radicals were trapped with dimethylpyrrolidine N-oxide and characterized as spin adducts via EPR. Cumyloxyl radicals were liberated in a similar manner from N-cumyloxy-5-(4-methoxyphenyl)-4-methylthiazole-2(3H)-thione. A noteworthy bathochromic shift was found for the lowest energy transition of N-(hydroxy)indeno[2,1-d]thiazole-2(3H)-thione (λmax=376 nm), if compared to the UV-vis absorption of N-hydroxy-4-methyl-5-phenylthiazole-2(3H)-thione (λmax=338 nm). Syntheses of alkoxyl radical precursors and procedures for conducting N,O-homolysis are described in a full account.

2-Benzyl-2-methyl-2H-benzimidazole 1,3-dioxide derivatives: Spectroscopic and theoretical study

The spectroscopic behavior of 2-benzyl-2-methyl-2H-benzimidazole 1,3-dioxide derivatives in solution was studied in terms of electronic and nuclear magnetic resonance (1H and 13C NMR) techniques. The experimental spectra were compared to the theoretical ones, obtained at DFT level, proving that the compounds adopt in solution a bird-like conformational distribution. Also, theoretically this conformational distribution resulted the most stable in gas phase. Infrared spectroscopy was used to study solid state behavior identifying experimentally the N-O stretching near to 1380, 1365 and 1225 cm-1 and the vibrational benzimidazole skeleton near to 1610 and 1590 cm-1. The vibrational spectrum was satisfactorily described by DFT calculations funding the N-O stretching as a coupled vibration near to 1470, 1350 and 1285 cm-1. The fragmentation that takes place in mass spectrometry was assigned for all of the new derivatives.

Inter- and Intramolecular Cycloadditions of Nitroalkenes with Olefins. 2-Nitrostyrenes

Aromatic nitroalkenes 9 - 12 underwent Lewis acid catalyzed cycloadditions with various cyclic alkenes to afford high yields of nitronates 25 - 30 with exclusive anti selectivity.Hammett studies helped to further delineate the role of the Lewis acid.Reaction of nitroalkenes 8 and 10 with various cyclic dienes in the presence of a Lewis acid demonstrated the ability of nitroalkenes to behave as dienes in cycloadditions.The major products were the syn diastereomers which arise from an endo-folded transition structure.Finally, intramolecular cycloaddition of 36 - 39 allowed a correlation between the stereochemical course of the reaction and positions of sp2 centers in the tether to be addressed.

Kinetics of reaction of para-substituted β-nitrostyrenes and β-methyl-β-nitrostyrenes with n-butylamine

The kinetics of addition of n-butylamine to β-nitrostyrene and β-methyl-β-nitrostyrene and their para-substituted derivatives in acetonitrile at four different temperatures have been followed spectrophotometrically.The order in is unity and in (n-butylamine) it is non-integral.On the basis of the observed kinetic data, a stepwise mechanism involving the formation of zwitterionic addition complex in an equilibrium step followed by conversion into the reaction product via proton transfer in catalytic route by the amine has been proposed.The study of effect of substituents in these reactions shows that the electron-withdrawing substituents accelerate the reaction and electronreleasing substituents retard it.Good Hammett correlations have been observed in both the reaction series.

HENRY CONDENSATION UNDER HIGH PRESSURE. 2. EFFECT OF AROMATIC ALDEHYDE TYPE AND PRESSURE ON THE YIELD OF ω-NITROSTYRENES AND SECONDARY PROCESSES

Condensation of aromatic aldehydes (I)-(XX) with EtNO2 and n-PrNO2 in AcOH in the presence of AcONH4 or i-BuNH2 gives primarily ω-nitrostyrenes (Ia, b) - (XXa, b) and small quantities of nitriles (Ic) - (XXc), oximes (Id) - (XXd), and ketones (Ie, f) - (XXe, f).The yields of (Ia, b) - (XXa, b) at P = 1 atm are higher for acceptor substitutents on the aromatic ring whereas at P = 10 kbar, they are higher for donor substituents.High pressures suppress the formation of (Ic-f) - (XXc-f) and the Z-isomers of (Ia, b) - (XXa, b).The high pressure technique is especially useful in the preparation of donor-substituted (Ia, b) - (XXa, b) which are intermediates in the synthesis of the psychotropic β-phenylethylamines.