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
• Article Data: 36

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

Description

(E)-2-Chlorostilbene is a chemical compound belonging to the stilbene class of organic compounds. It is a white to light yellow solid that is insoluble in water but soluble in organic solvents. (E)-2-Chlorostilbene has been identified as a potential intermediate in the synthesis of active pharmaceutical ingredients, and its properties are of interest in the investigation of its potential therapeutic applications. Additionally, (E)-2-Chlorostilbene has been studied for its potential environmental impact and toxicological properties.

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

• 1657-51-8 (Z)-1-chloro-2-styrylbenzene 
• 7514-02-5 α-Phenyl-o-chlor-zimtsaeure 
• 100-42-5 styrene 
• 10560-52-8 acetic acid-(2-chloro-N-nitroso-anilide) 
• 95-51-2 o-chloroaniline 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 89-98-5 2-chloro-benzaldehyde 
• 100-52-7 benzaldehyde 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 102-04-5 1,3-Diphenylpropanone 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 728-04-1 trans-α-(2'-chlorophenyl)cinnamic acid 
• 140-10-3 (E)-3-phenylacrylic acid 
• 89-90-7 2-chlorobenzenediazonium chloride 

Downstream Products

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

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.

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.

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.