1657-52-9

Basic information

• Product Name: (E)-2-Chlorostilbene
• Synonyms: (E)-1-(2-Chlorophenyl)-2-phenylethene;(E)-2-Chlorostilbene
• CAS NO: 1657-52-9
• Molecular Formula: C₁₄H₁₁Cl
• Molecular Weight: 214.69
• Mol File: 1657-52-9.mol

Chemical Properties

• Melting Point: 39.5°C
• Boiling Point: 278.18°C (rough estimate)
• Appearance: /
• Density: 1.1475 (rough estimate)
• Refractive Index: 1.6012 (estimate)
• CAS DataBase Reference: (E)-2-Chlorostilbene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-Chlorostilbene(1657-52-9)
• EPA Substance Registry System: (E)-2-Chlorostilbene(1657-52-9)

Safety Data

• Hazardous Substances Data: 1657-52-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(E)-2-Chlorostilbene is used as an intermediate in the synthesis of other chemicals and pharmaceuticals, contributing to the development of new compounds with various applications.
Used in Research Applications:
(E)-2-Chlorostilbene is utilized in research applications across the fields of organic chemistry, biochemistry, and pharmacology, aiding in the understanding of its properties and potential therapeutic uses.
Used in Pharmaceutical Development:
(E)-2-Chlorostilbene is considered as a potential intermediate for the synthesis of active pharmaceutical ingredients, which could lead to the creation of new medications with various therapeutic benefits.
Used in Environmental and Toxicological Studies:
(E)-2-Chlorostilbene is also studied for its potential environmental impact and toxicological properties, which is crucial for assessing its safety and suitability for various applications.

Upstream product

• 7514-02-5 α-Phenyl-o-chlor-zimtsaeure 
• 22568-07-6 1-chloro-2-(2-nitrovinyl)benzene 
• 94-36-0 dibenzoyl peroxide 
• 108-86-1 bromobenzene 
• 2039-87-4 2-chlorostyrene 
• 1657-51-8 (Z)-1-chloro-2-styrylbenzene 
• 23265-32-9 1-(methylsulfonyl)-2-(phenyl)diazene 
• 3112-88-7 Benzyl phenyl sulfone 
• 89-98-5 2-chloro-benzaldehyde 
• 10271-57-5 1-chloro-2-(2-phenylethynyl)benzene 
• 694-80-4 2-bromo-1-chlorobenzene 
• 83947-56-2 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane 
• 704-96-1 trans-2-chlorocinnamic acid 
• 36719-71-8 1-phenyl-3,3-tetramethylenetriazene 

Downstream Products

• 85-01-8 phenanthrene 
• 1657-51-8 (Z)-1-chloro-2-styrylbenzene 
• 52231-33-1 trans-2-p-Toluoylstilben 
• 52095-24-6 (E)-1-{2-[2-phenylvinyl]phenyl}ethanone 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 80663-50-9 2-((1E)-2-phenylvinyl)benzenecarbonitrile 
• 5162-03-8 (2-chlorophenyl)(phenyl)methanone 
• 34082-45-6 1-(2-chlorophenyl)-2-phenylethane-1,2-dione 
• 34662-94-7 1-phenyl-2-(2'-biphenylyl)ethylene 

Relevant articles and documents

A photocatalyst-free visible-light-mediated solvent-switchable route to stilbenes/vinyl sulfones from β-nitrostyrenes and arylazo sulfones

Photocatalyst-free visible-light-mediated reactions, based on the presence of a visible-light-absorbing functional group in the starting material itself in order to exclude the often costly, hazardous, degradable and difficult to remove or recover photoredox catalysts, have been gaining momentum recently. We have employed this approach to develop a denitrative photocatalyst-free visible-light-mediated protocol for the arylation/sulfonylation of β-nitrostyrenes employing arylazo sulfones (bench-stable photolabile compounds) in a switchable solvent-controlled manner. Arylazo sulfones served as the aryl and sulfonyl radical precursors under blue LED irradiation for the synthesis oftrans-stilbenes and (E)-vinyl sulfones in CH3CN and dioxane/H2O 2?:?1, respectively. The absence of any metal, photocatalyst and additive; excellent selectivity (E-stereochemistry) and solvent-switchability; and the use of visible light and ambient temperature are the prime assets of the developed method. Moreover, we report the first photocatalyst-free visible light-driven route to synthesize stilbenes and vinyl sulfones from readily available β-nitrostyrenes.

Custom-Made Pyrene Photocatalyst-Promoted Desulfonylation of Arylethenyl Sulfones Using Green-Light-Emitting Diodes

The Sonogashira coupling of 1,3,6,8-tetrabromopyrene with 4-[(-)-β-citronellyloxy]phenylethyne was employed to synthesize 1,3,6,8-tetra[4-(citronellyloxy)phenylethynyl]pyrene. The pyrene derivative catalyzed the reductive desulfonylation of ethenyl sulfones via visible-light irradiation (514 nm green light-emitting diodes) in the presence of i -Pr 2NEt. The β-citronellyloxy groups provided the sufficient solubility to the highly π-expanded pyrene catalyst, and their polar oxygen functionalities enabled the easy separation of the catalyst from the products via column chromatography.

A Bidentate Ru(II)-NC Complex as a Catalyst for Semihydrogenation of Alkynes to (E)-Alkenes with Ethanol

Four Ru(II)-NC complexes were tested as catalysts for semihydrogenation of internal alkynes to (E)-alkenes with ethanol, and the complex {(C5H4N)(C6H4)}RuCl(CO)(PPh3)2 (1a) showed the highest activity. The reactions proceeded well with 1 mol % catalyst loading and 0.1 equiv of t-BuONa at 110 °C for 1 h, and 32 alkenes were synthesized with excellent E:Z selectivity. This is the first ruthenium-catalyzed semihydrogenation of internal alkynes to (E)-alkenes using ethanol as the hydrogen donor.

Mizoroki-Heck Cross-Coupling of Bromobenzenes with Styrenes: Another Example of Pd-Catalyzed Cross-Coupling with Potential Safety Hazards

The potential safety hazards associated with the Mizoroki-Heck cross-coupling of bromobenzenes with styrenes were evaluated. The heat output from the reaction in various solvents was comparable in a variety of solvents; however, the rate of reaction was significantly faster in the presence of water. Thermal stability evaluation of the postreaction mixtures in DMSO and 3:1 DMSO/water by differential scanning calorimetry indicated that the onset temperatures of thermal decomposition were significantly lower than that of neat DMSO. Evaluation of the substrate scope revealed that the substitution pattern on the bromobenzene did not affect the heat output. The reaction rate of electron-deficient bromobenzenes was slower than that of the electron-rich bromobenzenes. In general, substituted styrenes afforded similar magnitudes of exotherms; however, the reaction rate of bromobenzene with 2-methylstyrene was significantly slower than the other studied styrenes. The predicted heat of reaction using the density functional theory method, B3LYP, was in good agreement with the experimental data. Such excellent agreement suggests that this calculation method can be used as a preliminary tool to predict heat of reaction and avoid exothermic reaction conditions. In many of the studied cases, the maximum temperature of a synthesis reaction was considerably higher than the solvent boiling point and thermal decomposition onset temperatures when the reaction was performed in DMSO or 3:1 DMSO/water. It is crucial to understand the thermal stability of the reaction mixture to design the process accordingly and ensure the reaction temperature is maintained below the onset temperature of decomposition to avoid potential runaway reactions.

Stereocontrolled synthesis of (E)-stilbene derivatives by palladium-catalyzed Suzuki-Miyaura cross-coupling reaction

A general procedure for the stereocontrolled synthesis of (E)-stilbene derivatives by palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of (E)-2-phenylethenylboronic acid pinacol ester with aryl bromides was investigated. (E)-2-Phenylethenylboronic acid pinacol ester was prepared by 9-BBN-catalyzed hydroboration of phenylacetylene with pinacolborane. This reagent undergoes facile palladium-catalyzed cross-coupling with a diverse set of aryl bromides to provide the corresponding (E)-stilbene derivatives in moderate to good yield. The use of the sterically bulky t-Bu3PHBF4 ligand was crucial to the successful coupling of electron-rich and electron-poor aryl bromides. Complete stereochemical retention of the (E)-2-phenylethenylboronic acid pinacol ester alkene geometry was observed in all of the (E)-stilbene derivatives synthesized.

Decarboxylative Arylation of α,β-Unsaturated Carboxylic Acids Using Aryl Triazenes by Copper/Ionic Liquid Combination in PEG-400

A practical method for the construction of stilbene derivatives has been developed via catalytic cross-coupling of cinnamic acids with aryl triazenes. The methodology offers high stereoselectivity and is endowed with broad substrate scope, high yield, and significant functional group tolerance.

Synthesis of 1,2-diarylethylenes by Pd-catalyzed one-pot reaction of benzyl halides, tosylhydrazide, and aryl aldehydes

Background: Substituted olefins are versatile functional groups and intermediates in chemistry, medicine, electronics, and optics and materials science fields because of their unique properties. One important class of substituted olefins 1,2-diarylethylenes have attracted considerable attention due to their presence in both natural products and pharmacologically active substances. Methods: In this paper, we developed a one-pot two-step coupling reaction of aryl aldehydes, tosylhydrazide with benzyl halides by using inexpensive Pd(PPh3)4 as catalyst, leading to a variety of 1,2- diphenylethenes derivatives with moderate to good yields. Results: The desired 1,2-diarylethylenes were obtained in 46-96% yields via Pd(0)-catalyzed one-pot reaction of benzyl halides, tosylhydrazide, and aryl aldehydes. Conclusion: The catalytic system presented here enables the use of easily accessible starting materials and good functional group tolerance.

Palladium/copper-catalyzed arylation of alkenes with N′-acyl arylhydrazines

A novel ligand-free palladium/copper-catalyzed Heck-type coupling reaction of alkenes and N′-acyl arylhydrazines has been developed by using air as the terminal oxidant. This protocol features wide functional group tolerance and produces highly chemoselective and regioselective products with good to excellent yields.

Metal-free denitrative arylation of β-nitrostyrenes using benzoyl peroxide: An easy access to: Trans -stilbenes

A simple, novel and stereoselective synthesis of trans-stilbenes has been described using denitrative arylation of β-nitrostyrenes in the presence of benzoyl peroxide under metal-free conditions. The reaction is assumed to involve homolytic cleavage of benzoyl peroxide followed by decarboxylation to generate a phenyl radical, which brings about ipso-substitution of the nitro group of nitrostyrenes to afford trans-stilbenes.

Selective Semihydrogenation of Alkynes with N-Graphitic-Modified Cobalt Nanoparticles Supported on Silica

For the first time N-graphitic-modified cobalt nanoparticles (Co/phen@SiO2-800) are shown to be active in the semihydrogenation of alkynes to alkenes. Key to success for efficient catalysis is both the modification of the metal nanoparticles by nitrogen-doped graphitic layers and the use of silica as support. Several internal alkynes are converted to the Z isomer in high yields with up to 93% selectivity. In addition, a variety of terminal alkynes, including sensitive functionalized compounds, are readily converted into terminal alkenes. Notably, this non-noble-metal catalyst allows for the purification of alkenes by selective hydrogenation of the corresponding alkyne in the presence of an excess of olefin.