1657-50-7

Basic information

• Product Name: (E)-1-(4-Chlorophenyl)-2-phenylethene
• Synonyms: (E)-1-(4-Chlorophenyl)-2-phenylethene;(E)-4-Chlorostilbene
• CAS NO: 1657-50-7
• Molecular Formula: C₁₄H₁₁Cl
• Molecular Weight: 214.69
• Mol File: 1657-50-7.mol
• Article Data: 403

Chemical Properties

• Melting Point: 129.6-130.2 °C
• Boiling Point: 324.8±17.0 °C(Predicted)
• Appearance: /
• Density: 1.163±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (E)-1-(4-Chlorophenyl)-2-phenylethene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(4-Chlorophenyl)-2-phenylethene(1657-50-7)
• EPA Substance Registry System: (E)-1-(4-Chlorophenyl)-2-phenylethene(1657-50-7)

Safety Data

• Hazardous Substances Data: 1657-50-7(Hazardous Substances Data)

Usage

Description

(E)-1-(4-Chlorophenyl)-2-phenylethene, commonly known as stilbene, is a chemical compound characterized by its molecular formula C14H11Cl. It presents as a colorless to pale yellow crystalline solid, which is insoluble in water but readily soluble in organic solvents. (E)-1-(4-Chlorophenyl)-2-phenylethene is recognized for its significance in the synthesis of a variety of other organic compounds and its role as a key intermediate in the production of dyes, optical brighteners, and pharmaceuticals. Additionally, stilbene is valued for its fluorescent properties, making it a component in the manufacturing of fluorescent whitening agents. Its potential applications extend across the fields of organic synthesis, materials science, and pharmaceutical research.

Uses

Used in Organic Synthesis:
Stilbene is utilized as a starting material for the synthesis of various other organic compounds, making it a fundamental component in the creation of a wide array of chemical products.
Used in Dye Production:
As a key intermediate, (E)-1-(4-Chlorophenyl)-2-phenylethene is used in the production of dyes, contributing to the coloration and enhancement of various materials.
Used in Pharmaceutical Industry:
Stilbene serves as an important intermediate in the pharmaceutical industry, playing a role in the development and manufacturing of certain medications.
Used in Optical Brighteners:
(E)-1-(4-Chlorophenyl)-2-phenylethene is also employed in the production of optical brighteners, which are used to improve the appearance of materials by making them appear more vibrant and luminous.
Used in Fluorescent Whitening Agents:
Capitalizing on its fluorescent properties, (E)-1-(4-Chlorophenyl)-2-phenylethene is used in the manufacturing of fluorescent whitening agents, which are additives that give a whiter appearance to fabrics and other materials.
Used in Materials Science:
Stilbene's unique properties make it a valuable component in the field of materials science, where it can be used to develop new materials with specific characteristics and applications.

Upstream product

• 73789-34-1 cinnamic acid 4-chlorophenyl ester 
• 444666-99-3 (E)-3-(4-chlorophenyl)acrylic acid phenyl ester 
• 100-42-5 styrene 
• 106-39-8 bromochlorobenzene 
• 19277-54-4 p-chlorophenyldiazomethane 
• 908094-04-2 phenyldiazomethane 
• 1073-67-2 4-vinylbenzyl chloride 
• 108-86-1 bromobenzene 
• 329-98-6 phenylmethylsulphonyl fluoride 
• 104-88-1 4-chlorobenzaldehyde 
• 72646-24-3 P-(benzylidene)methyldiphenylphosphorane 
• 128160-29-2 C₁₉H₃₄BrSb 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 51044-12-3 (4-chlorobenzyl)triphenylphosphonium bromide 

Downstream Products

• 50793-42-5 meso-4-chlorostilbene dibromide 
• 28291-10-3 trans-2-(4-chlorobenzenyl)-3-phenyl-oxirane 
• 70712-72-0 1,2-Diadamant-1-yl-1,2-diphenylethan 
• 87286-95-1 1-Adamant-1-yl-1,2-diphenylethan 
• 72301-40-7 threo-1-fluoro-2-hydroxy-1-(4-chlorophenyl)-2-phenylethane 
• 72301-41-8 threo-1-fluoro-2-hydroxy-1-phenyl-2-(4-chlorophenyl)ethane 
• 72301-38-3 Trifluoro-acetic acid 2-(4-chloro-phenyl)-2-fluoro-1-phenyl-ethyl ester 
• 72301-39-4 Trifluoro-acetic acid 1-(4-chloro-phenyl)-2-fluoro-2-phenyl-ethyl ester 
• 28291-10-3 2-(4-chlorophenyl)-3-phenyloxirane 
• 42291-06-5 α-phenyl-β-(4-chlorophenyl)ethylamine 
• 79564-65-1 1-(4-chlorophenyl)-2-phenylethan-1-amine 
• 76583-57-8 1-[3-(4-Chloro-phenyl)-4,5-diphenyl-1H-pyrrol-2-yl]-isoquinoline 
• 22711-23-5 4-chlorobenzil 
• 1657-49-4 1-chloro-4-[(Z)-2-phenylethenyl]benzene 

Relevant articles and documents

On the involvement of palladium nanoparticles in the Heck and Suzuki reactions

We describe two different pathways by which palladium-catalyzed Heck and Suzuki coupling reactions take place. When sol-gel entrapped palladium acetate was used as a catalyst, the reactions proceed by the formation of metallic nanoparticles. Such particle

Ultrasound promoted C-C bond formation: Heck reaction at ambient conditions in room temperature ionic liquids

Heck reaction proceeds at ambient temperature (30 °C) with considerably enhanced reaction rate (1.5-3 h) through the formation of Pd-biscarbene complexes and stabilized clusters of zero-valent Pd nanoparticles in ionic liquids under ultrasonic irradiation.

Ruthenium-Catalyzed E-Selective Partial Hydrogenation of Alkynes under Transfer-Hydrogenation Conditions using Paraformaldehyde as Hydrogen Source

E-alkenes were synthesized with up to 100 % E/Z selectivity via ruthenium-catalyzed partial hydrogenation of different aliphatic and aromatic alkynes under transfer-hydrogenation conditions. Paraformaldehyde as a safe, cheap and easily available solid hydrogen carrier was used for the first time as hydrogen source in the presence of water for transfer-hydrogenation of alkynes. Optimization reactions showed the best results for the commercially available binuclear [Ru(p-cymene)Cl2]2 complex as pre-catalyst in combination with 2,2-bis(diphenylphosphino)-1,1-binaphthyl (BINAP) as ligand (1 : 1 ratio per Ru monomer to ligand). Mechanistic investigations showed that the origin of E-selectivity in this reaction is the fast Z to E isomerization of the formed alkenes. Mild reaction conditions plus the use of cheap, easily available and safe materials as well as simple setup and inexpensive catalyst turn this protocol into a feasible and promising stereo complementary procedure to the well-known Z-selective Lindlar reduction in late-stage syntheses. This procedure can also be used for the production of deuterated alkenes simply using d2-paraformaldehyde and D2O mixtures.

Pd supported on clicked cellulose-modified magnetite-graphene oxide nanocomposite for C-C coupling reactions in deep eutectic solvent

Cellulose-modified magnetite-graphene oxide nanocomposite was prepared via click reaction and utilized for immobilization of palladium (Pd) nanoparticles without using additional reducing agent. The abundant OH groups of cellulose provided the uniform dispersion and high stability of Pd nanoparticles, while magnetite-graphene oxide as a supporting material offered high specific surface area and easy magnetic separation. The as-prepared nanocomposite served as a heterogeneous catalyst for the Heck and Sonogashira coupling reactions in various hydrophilic and hydrophobic deep eutectic solvents (DESs) as sustainable and environmentally benign reaction media. Among the fifteen DESs evaluated for coupling reactions, the hydrophilic DES composed of dimethyl ammonium chloride and glycerol exhibited the best results. Due to the low miscibility of catalyst and DES in organic solvents, the separated aqueous phase containing both of the catalyst and DES can be readily recovered by evaporating water and retrieved eight times with negligible loss of catalytic performance.