5043-91-4

Basic information

• Product Name: 1-chloro-4-[2-(4-methoxyphenyl)ethenyl]benzene
• CAS NO: 5043-91-4
• Molecular Formula: C₁₅H₁₃ClO
• Molecular Weight: 244.7161
• Mol File: 5043-91-4.mol
• Article Data: 71

Chemical Properties

• Boiling Point: 375.8°C at 760 mmHg
• Flash Point: 179.8°C
• Density: 1.173g/cm³
• Vapor Pressure: 1.64E-05mmHg at 25°C
• Refractive Index: 1.64
• CAS DataBase Reference: 1-chloro-4-[2-(4-methoxyphenyl)ethenyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chloro-4-[2-(4-methoxyphenyl)ethenyl]benzene(5043-91-4)
• EPA Substance Registry System: 1-chloro-4-[2-(4-methoxyphenyl)ethenyl]benzene(5043-91-4)

Safety Data

• Hazardous Substances Data: 5043-91-4(Hazardous Substances Data)

Usage

SMILES code

OC(=O)C=CC1=C(C=CC(C2=CC=C(Cl)C=C2)=C1)C(=O)C

Molecular weight

252.73 g/mol

Functional groups

Chlorine atom, methoxy group, phenyl ring, vinyl group

Structure

Contains two phenyl rings connected by a vinyl group, with a chlorine atom and a methoxy group attached to one of the phenyl rings

Physical state

Likely a solid at room temperature, based on its molecular weight and structure

Applications

Used in organic synthesis and research as a starting material for the production of various pharmaceuticals, agrochemicals, and dyes; used as a building block for the synthesis of various organic compounds; has applications in the field of medicinal chemistry

Environmental considerations

Potential environmental pollutant; should be handled and disposed of with care to minimize its impact on the environment

Hazards

Not specified in the provided material, but may include toxicity, flammability, or reactivity with other substances, depending on its specific properties and handling conditions.

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 135705-51-0 p-chlorobenzyldibutyltelluronium bromide 
• 105336-81-0 4(C₅H₅)^(1-)*2Zr⁽⁴⁺⁾*2(NNCHC₆H₄OCH₃)^(2-)=((C₅H₅)2ZrNNCHC₆H₄OCH₃)2 
• 104-88-1 4-chlorobenzaldehyde 
• 1073-67-2 4-vinylbenzyl chloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 696-62-8 para-iodoanisole 
• 637-69-4 4-Methoxystyrene 
• 106-39-8 bromochlorobenzene 
• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 622-95-7 4-chlorobenzyl bromide 
• 1177254-38-4 2,2,4,4-tetramethyl-3-(4-chloro)benzylidene-1,5-dioxa-2,4-disilacycloheptane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 105336-83-2 4(C₅H₅)^(1-)*2Zr⁽⁴⁺⁾*2(NNCHC₆H₅)^(2-)=((C₅H₅)2ZrNNCHC₆H₅)2 

Downstream Products

• 2131-84-2 1-methoxy-4-(4-styrylstyryl)benzene 
• 1608492-52-9 (2R,3S,4R,5S)-3,4-bis(4-chlorophenyl)2,5-bis(4-methoxyphenyl)tetrahydrofuran 
• 5043-91-4 (E)-4-chloro-4'-methoxystilbene 
• 54945-17-4 1-(4-chlorophenyl)-2-(4-methoxyphenyl)-ethane-1,2-dione 
• 1333128-06-5 5-[4-[(E)-2-(4-methoxyphenyl)vinyl]phenyl]-1,2-dimethylimidazole 
• 1333128-07-6 3-[4-[2-(4-methoxyphenyl)ethenyl]phenyl]imidazo[1,2-a]pyridine 
• 18951-46-7 (E)-4-<2-(4-chlorophenyl)ethenyl>phenol 
• 1588534-24-0 C₂₈H₂₀Cl₂O₂ 
• 10547-60-1 4-chloro-4'-methoxybenzophenone 

Relevant articles and documents

Synthesis, crystal structure, and catalytic activity of bridged-bis(N-heterocyclic carbene) palladium(II) complexes in selective Mizoroki-Heck cross-coupling reactions

A series of three 1,3-propanediyl bridged bis(N-heterocyclic carbene)palladium(II) complexes (Pd-BNH1, Pd-BNH2, and Pd-BNH3), with + I effect order of the N-substituents of the ligand (isopropyl > benzyl > methoxyphenyl), was the subject of a spectroscopic, structural, computational and catalytic investigation. The bis(NHC)PdBr2 complexes were evaluated in Mizoroki-Heck coupling reactions of aryl bromides with styrene or acrylate derivatives and showed high catalytic efficiency to produce diarylethenes and cinnamic acid derivatives. The X-ray structure of the most active palladium complex Pd-BNH3 shows that the Pd(II) center is bonded to the two carbon atoms of the bis(N-heterocyclic carbene) and two bromide ligands in cis position, resulting in a distorted square planar geometry. The NMR data of Pd-BNH3 are consistent with a single chair-boat rigid conformer in solution with no dynamic behavior of the 8-membered ring palladacycle in the temperature range 25–120 °C. The catalytic activities of three Pd-bridged bis(NHC) complexes in the Mizoroki-Heck cross-coupling reactions were not found to have a direct correlation with +I effect order of the N-substituents of the ligand. However, a direct correlation was found between the DFT calculated absolute softness of the three complexes with their respective catalytic activity. The highest calculated softness, in the case of Pd-BNH3, is expected to favor the coordination steps of both the soft aryl bromides and alkenes in the Heck catalytic cycle.

Transition-Metal-Free Matsuda-Heck Type Cross-Coupling and Mechanistic Evidence for a Radical Mechanism

The Matsuda-Heck reaction, usually performed with palladium catalysts, can be carried out under transition-metal-free conditions in the presence of a KOtBu/DMF couple. This system allows the selective and direct synthesis of stilbenes from aryldiazonium salts under mild temperature (20 °C). Mechanistic studies suggest a radical pathway in which the DMF acts as the initiator of the overall process.

Diarylethene synthesis method without transition metal catalysis

The invention discloses a diarylethene synthesis method without transition metal catalysis. The method comprises the following steps: a cinnamic acid derivative and aryl trifluoroborate are subjectedto a decarboxylation coupling reaction in a solvent under the action of an oxidizing agent, postprocessing is performed after the reaction, and diarylethene is obtained. K2S2O8 is adopted to promote acatalytic system in the synthetic method, and a free radical coupling reaction can be performed directly under the condition that no ligand, transition metal or alkali is added. The method has widersubstrate range and higher yield; the method is simple to operate, reaction conditions are mild, and large-scale application is facilitated.