444608-64-4

Basic information

• Product Name: 1-[2-(4-methoxyphenyl)vinyl]-2-methylbenzene
• Synonyms: 1-[2-(4-methoxyphenyl)vinyl]-2-methylbenzene;Benzene, 1-[(1E)-2-(4-methoxyphenyl)ethenyl]-2-methyl-
• CAS NO: 444608-64-4
• Molecular Formula: C₁₆H₁₆O
• Molecular Weight: 224.3
• Mol File: 444608-64-4.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-[2-(4-methoxyphenyl)vinyl]-2-methylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2-(4-methoxyphenyl)vinyl]-2-methylbenzene(444608-64-4)
• EPA Substance Registry System: 1-[2-(4-methoxyphenyl)vinyl]-2-methylbenzene(444608-64-4)

Safety Data

• Hazardous Substances Data: 444608-64-4(Hazardous Substances Data)

Upstream product

• 637-69-4 4-Methoxystyrene 
• 2093-46-1 2-methylphenyl diazonium tetrafluoroborate 
• 917471-59-1 2-(p-methoxystyryl)-α,α,α-trifluorotoluene 
• 444-29-1 2-iodo(trifluoromethyl)benzene 
• 1093686-51-1 O,O-diethyl 1-o-tolylvinylphosphate 
• 93296-09-4 4-methoxyphenylzinc chloride 
• 22390-98-3 1-(4-methoxyphenyl)ethenyl acetate 
• 16419-60-6 2-Methylphenylboronic acid 
• 95-46-5 2-methylphenyl bromide 
• 932-31-0 ortho-tolylmagnesium bromide 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 529-27-1 2-methylphenylhydrazine 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 130248-57-6 (E)-2-(2-methylphenyl)-1-iodo-1-ethene 

Relevant articles and documents

Stereospecific Iron-Catalyzed Carbon (sp2)-Carbon (sp2) Cross-Coupling of Aryllithium with Vinyl Halides

We present herein an efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners. More than 30 examples were obtained with moderate to good yields and high stereoselectivities. The practicality of this method is evidenced by a gram-scale synthesis. In addition, a preliminary mechanistic investigation was also performed.

Rapid Access to Ortho-Alkylated Vinylarenes from Aromatic Acids by Dearomatization and Tandem Decarboxylative C-H Olefination/Rearomatization

A two-step straightforward method for the preparation of ortho-alkylated vinylarenes from readily available benzoic acids is described. The synthetic route involves the dearomatization of benzoic acids by Birch reduction providing alkylated cyclohexa-2,5-dienyl-1-carboxylic acids. The diene subsequently undergoes a decarboxylative C-H olefination followed by rearomatization to deliver ortho-alkylated vinylarene. Mechanistic studies suggest that a Pd/Ag bimetallic catalytic system is important in the tandem decarboxylative C-H olefination/rearomatization step.

Rhodium-Catalyzed Cross-Coupling of Vinylarenes with Arylaluminum Reagents in the Presence of Ketones

Rhodium-catalyzed addition/elimination of arylaluminum reagents with vinylarenes was achieved to obtain stilbene derivatives. The reaction of diethyl(phenyl)aluminum with styrene in the presence of the chloro(1,5-cyclooctadiene)rhodium(I) dimer, [RhCl(cod)]2, and diisopropyl ketone (2,4-dimethyl-3-pentanone) as an additive occurred to give (E)-stilbene in quantitative yield. The use of other arylaluminum reagents afforded β-arylated products in good to excellent yields. This reaction was found to be promoted by ketones as additives, which are reduced to the corresponding alcohols, as confirmed by analysis of the crude reaction mixture by 1H NMR spectroscopy.