67471-39-0

Basic information

• Product Name: 1-(4-chlorophenyl)ethenyl methyl ether
• CAS NO: 67471-39-0
• Molecular Formula: C₉H₉ClO
• Molecular Weight: 168.6202
• Mol File: 67471-39-0.mol

Chemical Properties

• Boiling Point: 237°C at 760 mmHg
• Flash Point: 101.8°C
• Density: 1.098g/cm³
• Vapor Pressure: 0.0707mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: 1-(4-chlorophenyl)ethenyl methyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-chlorophenyl)ethenyl methyl ether(67471-39-0)
• EPA Substance Registry System: 1-(4-chlorophenyl)ethenyl methyl ether(67471-39-0)

Safety Data

• Hazardous Substances Data: 67471-39-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-chlorophenyl)ethenyl methyl ether is utilized as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new medications and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(4-chlorophenyl)ethenyl methyl ether serves as a crucial intermediate for the production of pesticides and other agrochemicals, aiming to enhance crop protection and yield.
Used in Dye Manufacturing:
This chemical compound is employed as a synthetic intermediate in the manufacturing of dyes, playing a significant role in the creation of a wide range of colors and pigments for various applications.
Used in Perfumery and Flavoring Industry:
1-(4-chlorophenyl)ethenyl methyl ether is also used in the production of perfumes and flavorings, where it contributes to the development of unique scents and tastes for consumer products.
Safety Precautions:
Given its hazardous nature, 1-(4-chlorophenyl)ethenyl methyl ether requires careful handling to prevent irritation to the skin, eyes, and respiratory tract. It is essential to follow proper safety measures and precautions when working with this chemical compound.

Upstream product

• 83739-62-2 2-bromo-1-methoxy-1-(4-chlorophenyl)ethane 
• 99-91-2 para-chloroacetophenone 
• 77-78-1 dimethyl sulfate 
• 72360-69-1 4-chlorophenyl methyl ketone dimethyl acetal 
• 54149-82-5 1-(4-Chlorophenyl)-2,2-dimethoxyethanone 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 67-56-1 methanol 

Downstream Products

• 72360-69-1 4-chlorophenyl methyl ketone dimethyl acetal 
• 99-91-2 para-chloroacetophenone 
• 67-56-1 methanol 
• 119205-36-6 4-chloro-α-bromoacetophenone methyl hemiacetal 
• 1176756-84-5 methyl 2,2-dimethyl-3-(p-chlorophenyl)-3-butenoate 
• 99360-14-2 1-(4-chloro-phenyl)-propan-1-one semicarbazone 
• 6285-05-8 4'-chloropropiophenone 
• 74103-64-3 1,4-bis-(4-chloro-phenyl)-2-methyl-butane-1,4-dione 
• 7575-74-8 p-chloroacetophenone semicarbazone 
• 98-86-2 acetophenone 
• 93-55-0 1-phenyl-propan-1-one 

Relevant articles and documents

Coupling Reaction of Enol Derivatives with Silyl Ketene Acetals Catalyzed by Gallium Trihalides

A cross-coupling reaction between enol derivatives and silyl ketene acetals catalyzed by GaBr3took place to give the corresponding α-alkenyl esters. GaBr3showed the most effective catalytic ability, whereas other metal salts such as BF3?OEt2, AlCl3, PdCl2, and lanthanide triflates were not effective. Various types of enol ethers and vinyl carboxylates as enol derivatives are amenable to this coupling. The scope of the reaction with silyl ketene acetals was also broad. We successfully observed an alkylgallium intermediate by using NMR spectroscopy, suggesting a mechanism involving anti-carbogallation among GaBr3, an enol derivative, and a silyl ketene acetal, followed by syn-β-alkoxy elimination from the alkylgallium. Based on kinetic studies, the turnover-limiting step of the reaction using a vinyl ether and a vinyl carboxylate involved syn-β-alkoxy elimination and anti-carbogallation, respectively. Therefore, the leaving group had a significant effect on the progress of the reaction. Theoretical calculations analysis suggest that the moderate Lewis acidity of gallium would contribute to a flexible conformational change of the alkylgallium intermediate and to the cleavage of the carbon?oxygen bond in the β-alkoxy elimination process, which is the turnover-limiting step in the reaction between a vinyl ether and a silyl ketene acetal.

Gallium tribromide catalyzed coupling reaction of alkenyl ethers with ketene silyl acetals

A 'Ga'llant couple: The α-alkenylation of esters was accomplished by GaBr3-catalyzed coupling between alkenyl ethers and ketene silyl acetals. In this reaction system, various alkenyl ethers, including those with vinyl and substituted alkenyl groups, were applicable, and the scope of applicable ketene silyl acetals was sufficiently broad. The mechanism is also discussed. Copyright

THERMODINAMYCS OF THE ISODESMIC ENOL-TO-METHYL ENOL ETHER EQUILIBRIUM IN WATER

ΔGo values for the isodesmic equilibrium between substituted acetophenone enols and corresponding methyl enol ethers are calculated from previously reported data on equilibrium constants for keto-enol tautomerism and for enol ether formation from ketones.These values agree with those expected from literature data on analogous alcohol-ether isodesmic systems.

Carbonyl Methylenation Using a Titanium- Aluminum (Tebbe) Complex

The titanium-aluminum (Tebbe) complex is shown to be an effective methylenating agent for a variety of carbonyl groups.The reaction is unique in that the carbonyl groups of carboxylic acid derivatives are readily methylenated.Thus vinyl enol ethers are prepared from esters and enamines are formed from amides.The complex provides a method for methylenating hindered or base sensitive ketones that is advantageous to the Wittig reagent.Selective methylenation of dicarbonyl compounds is also accomplished.

The Allopolarization Principle and its Applications, IV. Substituent Effects in the Methylation of Enolate Anions

The ratio of O- and C-methylated products in the reaction of the sodium salts of acetophenones 1, propiophenones 3, phenylacetones 5, β-dicarbonyl compounds 12, α-cyanocarbonyl compounds 13, acetaldehyde, propionaldehyde, and diethylketone with dimethyl sulfate, methyl iodide, and trimethyl phosphate in HMPTA has been determined with regard to the effect of substituents.In some cases the influence of solvents, concentration and temperature has also been studied.