4747-13-1

Basic information

• Product Name: Methyl(1-phenylethenyl) ether
• Synonyms: (1-Methoxyethenyl)benzene;(1-Methoxyvinyl)benzene;1-Methoxy-1-phenylethene;Methyl 1-phenylvinyl ether;Methyl(1-phenylethenyl) ether
• CAS NO: 4747-13-1
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.18
• Mol File: 4747-13-1.mol
• Article Data: 45

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl(1-phenylethenyl) ether(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl(1-phenylethenyl) ether(4747-13-1)
• EPA Substance Registry System: Methyl(1-phenylethenyl) ether(4747-13-1)

Safety Data

• Hazardous Substances Data: 4747-13-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 1738, 1955 DOI: 10.1021/ja01612a006Synthesis, p. 144, 1988 DOI: 10.1055/s-1988-27495Tetrahedron Letters, 23, p. 631, 1982 DOI: 10.1016/S0040-4039(00)86908-7

Upstream product

• 13684-98-5 2-methoxy-2-phenylethyl iodide 
• 4316-35-2 acetophenone dimethyl acetal 
• 104-15-4 toluene-4-sulfonic acid 
• 100-42-5 styrene 
• 124-41-4 sodium methylate 
• 98-86-2 acetophenone 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 629-05-0 n-octyne 
• 1600-27-7 mercury(II) diacetate 
• 108415-87-8 2-methoxy-2-phenyl-1-(phenylselenonyl)ethane 
• 108415-83-4 (E)-β-styryl phenyl selenone 
• 93-58-3 benzoic acid methyl ester 
• 31729-70-1 bis(iodozinc)methane 

Downstream Products

• 942-92-7 caprophenone 
• 1669-49-4 3-(4-methoxyphenyl)-1-phenylpropan-1-one 
• 854211-65-7 (β-methoxy-styryl)-hydrazine-N,N'-dicarboxylic acid dimethyl ester 
• 495-71-6 phenacylacetophenone 
• 34557-54-5 methane 
• 1083-30-3 dihydrochalcone 
• 70271-76-0 4-ethyl-7-methoxy-7-phenyl-[1,4]oxazepane 
• 24243-63-8 1-Methoxy-1,4,4-triphenyl-buten-⁽¹⁾-on-⁽³⁾ 
• 40811-28-7 [1-Methoxy-2-(2-methyl-propenylidene)-cyclopropyl]-benzene 
• 78950-05-7 (E)-2-Methoxy-2-phenylcyclopropancarbonsaeure-ethylester 
• 78950-05-7 (Z)-2-Methoxy-2-phenylcyclopropancarbonsaeure-ethylester 
• 37385-32-3 3,4-diphenylpyridazine 
• 29526-97-4 1-methoxy-1-phenylcyclopropane 
• 155989-27-8 dimethyl 5-phenylpentan-5-one-2,3-dicarboxylate 

Relevant articles and documents

New Surprises with Fischer Carbene Complexes: Formal [3 + 2] Cycloadditions with and without Preceding Carbene-Ligand Metathesis

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Photoinduced Cross-Coupling of Aryl Iodides with Alkenes

A protocol for photoinduced cross-coupling of aryl iodides having polar π-functional groups or elongated π-conjugation with alkenes has been developed. The radical cascade mechanism involving generation of aryl radicals via C-I bond homolysis of photoexcited aryl iodides and their subsequent addition to alkenes is proposed. The method enables iodide-selective cross-coupling over other halogen leaving groups with functional group compatibility on both arene and alkene motifs.

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.