706-07-0

Basic information

• Product Name: 1-(4-Chlorophenyl)-2-nitroethene
• Synonyms: 4'-CHLORO-BETA-NITROSTYRENE;4-CHLORO-BETA-NITROSTYRENE;1-CHLORO-4-(2-NITRO-VINYL)-BENZENE;1-(4-CHLOROPHENYL)-2-NITROETHENE;TRANS-4-CHLORO-BETA-NITROSTYRENE;p-chloro-beta-nitro-styren;p-chloro-beta-nitro-styrene;trans-4-chloro-β-nitrostyrene
• CAS NO: 706-07-0
• Molecular Formula: C₈H₆ClNO₂
• Molecular Weight: 183.59
• Product Categories: Ethanes/ethenes;Alkenyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 706-07-0.mol

Chemical Properties

• Melting Point: 112-116 °C(lit.)
• Boiling Point: 299 °C at 760 mmHg
• Flash Point: 134.6 °C
• Appearance: /
• Density: 1.324 g/cm³
• Vapor Pressure: 0.00218mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-(4-Chlorophenyl)-2-nitroethene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Chlorophenyl)-2-nitroethene(706-07-0)
• EPA Substance Registry System: 1-(4-Chlorophenyl)-2-nitroethene(706-07-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• WGK Germany: 3
• RTECS: WL4200500
• HazardClass: IRRITANT
• Hazardous Substances Data: 706-07-0(Hazardous Substances Data)

Usage

Uses

Used in Medical Research:
1-(4-Chlorophenyl)-2-nitroethene is used as a research compound for its potential applications in the development of new pharmaceuticals. Its unique chemical structure allows for exploration in various therapeutic areas.
Used in Chemical Research:
1-(4-Chlorophenyl)-2-nitroethene is used as a chemical intermediate in the synthesis of other compounds, particularly in the field of organic chemistry. Its aromatic and nitro characteristics make it a valuable building block for creating new molecules with specific properties.
Used in Drug Development:
1-(4-Chlorophenyl)-2-nitroethene is used as a lead compound in the process of drug discovery, where its properties can be further modified to develop new therapeutic agents with improved efficacy and safety profiles.

InChI:InChI=1/C8H6ClNO2/c9-8-3-1-7(2-4-8)5-6-10(11)12/h1-6H/b6-5+

Upstream product

• 75-52-5 nitromethane 
• 104-88-1 4-chlorobenzaldehyde 
• 135711-37-4 Butyl-[1-(4-chloro-phenyl)-2-nitro-ethyl]-amine 
• 1073-67-2 4-vinylbenzyl chloride 
• 1749-03-7 N-(4-chlorobenzylidene)-4-methoxyaniline 
• 3395-81-1 4-chlorobenzaldehyde dimethyl acetal 
• 1615-02-7 p-chlorocinnamic acid 
• 89979-04-4 1-(4-chlorophenyl)-2-nitroethanol 
• 1075-77-0 4-chlorocinnamaldehyde 

Downstream Products

• 102451-67-2 3-[1-(4-chlorophenyl)-2-nitroethyl]-2-phenyl-1H-indole 
• 52809-72-0 (1-(4-chlorophenyl)-2-nitroethyl)(phenyl)sulfide 
• 107775-55-3 N-[1-(4-chloro-phenyl)-2-nitro-ethyl]-aniline 
• 10125-50-5 4-Chlor-1-<1,3,3,3-tetranitro-propyl-2>-benzol 
• 10125-48-1 4-Chlor-1-<1,3,3-trinitro-butyl-2>-benzol 
• 10125-49-2 4-Chlor-1-(1,3,3-trinitropentyl-2)-benzol 
• 50368-40-6 5-(4-chloro-phenyl)-3-methyl-2-thioxo-[1,3,4]thiadiazinan-6-one oxime 
• 29651-84-1 S-1-(4-chlorophenyl)-2-nitroethyl thiolacetate 
• 82947-78-2 [1-(4-Chloro-phenyl)-2-nitro-ethyl]-phosphonic acid dipropyl ester 
• 82947-82-8 [2-(4-Chloro-phenyl)-2-(dipropoxy-phosphoryl)-ethyl]-phosphonic acid dipropyl ester 
• 57544-20-4 2-(4-chlorophenyl)-6-methoxy-3-nitro-2H-chromene 
• 92774-82-8 2-[1-(4-Chloro-phenyl)-2-nitro-ethyl]-3-hydroxy-cyclopent-2-enone 
• 134435-14-6 3-<1-(4-chlorophenyl)-2-nitroethyl>isobenzofuran-1(3H)-one 
• 134435-13-5 dimethyl 1-<1-(4-chlorophenyl)-2-nitroethyl>-3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonate 

Relevant articles and documents

Microwave-assisted rapid synthesis of spirooxindole-pyrrolizidine analogues and their activity as anti-amyloidogenic agents

A library of Sox-pyrrolizidines was rapidly prepared by microwave-assisted, one-pot, three-component, 1,3-dipolar cycloaddition of azomethine ylides from l-proline and isatin, with various β-nitrostyrenes. Nitro-Sox compounds, 4b, 4d and 4e inhibit HEWL amyloid fibril formation by ThT studies with percentages of fluorescence intensity of 55.4, 42.9 and 40.3%, respectively. Further studies with MTT assay, Raman spectroscopy, TEM and molecular docking supported these promising candidates for activity against amyloid misfolding, a phenomenon leading to Alzheimer's disease pathology.

Palladium-Catalyzed Formal (3 + 2) Cycloaddition Reactions of 2-Nitro-1,3-enynes with Vinylaziridines, -epoxides, and -cyclopropanes

A two-step Pd-catalyzed (3 + 2) cycloaddition/HNO2 elimination reaction sequence has been developed to give novel cyclic 1,3-dien-5-yne systems from Pd-stabilized zwitterionic 1,3-dipoles and 2-nitro-1,3-enyne substrates. The process is highly atom-efficient and tolerates the reaction of 2-vinyloxirane, 1-tosyl-2-vinylaziridine, and diethyl 2-vinylcyclopropane-1,1-dicarboxylate derived 1,3-dipoles with a variety of 2-nitro-1,3-enyne substrates. The stereochemistry of the intermediate (3 + 2) cycloadducts was determined by single crystal X-ray analysis. Furthermore, a selective kinetic elimination of the cycloadduct with an antiperiplanar relationship between the NO2 group and the participating hydrogen was demonstrated, allowing for efficient isolation of a single diastereoisomer of the cycloadduct.

A green metal-free "one-pot" microwave assisted synthesis of 1,4-dihydrochromene triazoles

The synthesis of several 4-aryl-1,4-dihydrochromene-triazoles was achieved via a metal-free "one-pot"procedure using PEG400 as the sole solvent in an eco-friendly process. Using microwave irradiation, the triazole derivatives were obtained in good yields and short reaction times starting from readily accessible building blocks.

Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles

An asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been realized with a chiral bifunctional squaramide catalyst. This Michael/Friedel-Crafts cascade strategy provides a facile and efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.

Skeletally Tunable Seven-Membered-Ring Fused Pyrroles

We describe a copper-mediated method that enables the synthesis of seven-membered-ring fused pyrroles (7-mrFPs). The protocol proceeds via an in situ spiro-intermediate ring expansion and tolerates a library of 7-mrFP derivatives with a broad range of functional groups in a simple step with tangible parameters and substrate adaptations. These rare 7-mrFPs are now accessible on a millimolar scale, and selected examples exhibit high antioxidant activity.

Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid

The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ?NO2 radical is the active species.

A noncovalent hybrid of [Pd(phen)(OAc)2] and st-DNA for the enantioselective hydroamination of β-nitrostyrene with methoxyamine

We developed a novel Pd-catalysed enantioselective synthesis of C-N bonds using the chiral scaffold of DNA. The non-covalently linked [Pd(phen)(OAc)2] with st-DNA catalysed the Markonicov hydroamination of β-nitrostyrene with methoxyamine for the first time with >75% enantiomeric excess (ee) in an aqueous buffer (pH 7.4) at room temperature.

One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

β-Nitrostyrenes underwent a Diels-Alder reaction with Danishefsky's diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated-5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated-4-nitrophenols. The reaction of nitrostyrenes with Danishefsky's diene could be conducted in one pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group, e.g., a thienyl group could be introduced into the nitrophenol framework.

Porous Boron Nitride as a Weak Solid Base Catalyst

Porous boron nitride was synthesized by pyrolysis from boric acid and urea mixed in varying molar ratios. The boron nitride prepared had high surface areas ranging from 376 to 647 m2 g?1 with both microporous and mesoporous structures. The sample prepared with a urea-to-boric acid molar ratio of 5 exhibited the highest pore volume with the highest surface area of mesopores. Boron-K edge X-ray absorption fine structure spectroscopy revealed that the surface structure consisted of BN3 sites along with BN2O, BNO2, and BO3 sites. Fourier transform infrared (FTIR) spectroscopy indicated the formation of amino and hydroxyl groups on the surface. Analysis using color indicator reagents and deuterated chloroform-adsorbed FTIR results indicated that the porous boron nitride had very weak base sites of strength +7.2>H?≥+6.3. Porous boron nitride exhibited a high activity for the nitroaldol reaction with a high selectivity for nitroalkene (>97 %). A good correlation was observed between the catalytic activity of the boron nitride catalysts and their porous structures.

Facile Synthesis of 1,3,5-Triarylbenzenes and 4-Aryl-NH-1,2,3-Triazoles Using Mesoporous Pd-MCM-41 as Reusable Catalyst

We report mesoporous nano-Pd-MCM-41 catalyzed rapid and efficient synthesis of 1,3,5-triarylbenzenes via de-nitrative cyclotrimerization of β-nitrostyrenes. All the reactions were very fast and high yielding. The Pd-MCM-41 was also very effective in catalyzing de-nitrative [3+2] cycloaddition of β-nitrostyrenes with TMSN3 to synthesize 4-aryl-NH-1,2,3-triazoles. The catalyst was reused at least up to eight times with minimum loss of catalytic activity.