72233-10-4

Basic information

• Product Name: Benzene, 1-(3,3-diethoxy-1-propenyl)-4-methoxy-, (E)-
• CAS NO: 72233-10-4
• Molecular Formula: C14H20O3
• Molecular Weight: 236.311
• Mol File: 72233-10-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Benzene, 1-(3,3-diethoxy-1-propenyl)-4-methoxy-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-(3,3-diethoxy-1-propenyl)-4-methoxy-, (E)-(72233-10-4)
• EPA Substance Registry System: Benzene, 1-(3,3-diethoxy-1-propenyl)-4-methoxy-, (E)-(72233-10-4)

Safety Data

• Hazardous Substances Data: 72233-10-4(Hazardous Substances Data)

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 696-62-8 para-iodoanisole 
• 1963-36-6 4-methoxycinnamaldehyde 
• 122-51-0 orthoformic acid triethyl ester 
• 21960-26-9 (4-methoxybenzylidene)triphenylphosphorane 
• 5344-23-0 diethoxyacetaldehyde 

Downstream Products

• 82724-69-4 1-Methoxy-4-((1E,5E)-3,7,7-triethoxy-hepta-1,5-dienyl)-benzene 
• 89553-29-7 (E)-5-ethoxy-7-(p-methoxyphenyl)-2,6-heptadienal 
• 118326-21-9 1-((1E,5E)-3-Ethoxy-6-methyl-octa-1,5,7-trienyl)-4-methoxy-benzene 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 
• 1963-36-6 4-methoxycinnamaldehyde 
• 22767-72-2 ethyl 3-(4-methoxyphenyl)propanoate 
• 24056-44-8 C₁₈H₂₈O₄ 
• 72232-59-8 (2E,4E,6E)-7-(4-methoxyphenyl)hepta-2,4,6-trienal 
• 90714-17-3 3-(p-anisyl)-2,2-diphenylthio-1-formylcyclopropane 
• 90714-20-8 3-(p-anisyl)-2,2-diphenylthio-2,3-dihydrofuran 
• 90714-23-1 3-(p-anisyl)-2-phenylthiofuran 
• 90714-14-0 3-(p-anisyl)-1-formyl-2,2-dichlorocyclopropane 
• 60682-78-2 3-(p-anisyl)-2,2-dichloro-1-diethoxymethylcyclopropane 
• 1963-36-6 (Z)-3-(4-Methoxyphenyl)-2-propenal 

Relevant articles and documents

Fluorous oxime palladacycle: A precatalyst for carbon-carbon coupling reactions in aqueous and organic medium

To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon-carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.

Synthesis, characterization and primary evaluation of the synthetic efficiency of supported vinyltins and allyltins

Supported vinyltins and allyltins grafted to an insoluble cross-linked polystyrene matrix were prepared using methods usually employed in solution, like hydrostannylation of alkynes, transmetallation of a tin halide with organomagnesium or organozinc reagents, and substitution of an allyl halide by a supported stannylanion or SN2′ substitution of a supported β-stannylacrolein acetal by cyanocopper reagents in the presence of boron trifluoride etherate. The insoluble grafted organotin reagents were analysed by HRMAS NMR, allowing an unambiguous assignment of their isomeric distribution or the identification of side products. When involved in Stille cross-coupling reactions (vinyltins) or in addition on aldehydes (allyltins), these supported reagents exhibit similar reactivity and similar stereoselectivity when compared to the tributyltin analogues, with the advantage to prevent problems due to the contamination by tin residues.

Chemoselective Heck arylation of acrolein diethyl acetal catalyzed by an oxime-derived palladacycle

A dimeric 4-hydroxyacetophenone oxime-derived palladacycle has been used as a very efficient precatalyst for the chemoselective arylation of acrolein diethyl acetal to give either cinnamaldehyde derivatives or 3-arylpropanoate esters by proper choice of the reaction conditions. The synthesis of cinnamaldehyde derivatives can be performed by Heck reaction of acrolein diethyl acetal with iodo-, bromo- or chloroarenes in N,N-dimethylacetamide (DMA) using K2CO3 as base at 120°C and tetra-n-butylammonium acetate (TBAA) and KCl as additives, followed by acid workup. In the case of 3-arylpropanoate esters the corresponding arylation of acrolein diethyl acetal with iodoarenes can be performed at 90°C in aqueous DMA using (dicylohexyl)methylamine as base, whereas for bromoarenes the reaction has to be performed at 120°C using tetra-n-butylammonium bromide (TBAB) as additive. Alternatively, this process can be performed under microwave irradiation. These couplings take place in good yields and with lower catalyst loading than with palladium(II) acetate as well as in shorter reaction times and with lower excess of acrolein diethyl acetal.