453537-15-0

Basic information

• Product Name: Benzaldehyde, 4-(1-butoxyethenyl)-
• CAS NO: 453537-15-0
• Molecular Formula: C13H16O2
• Molecular Weight: 204.269
• Mol File: 453537-15-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzaldehyde, 4-(1-butoxyethenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 4-(1-butoxyethenyl)-(453537-15-0)
• EPA Substance Registry System: Benzaldehyde, 4-(1-butoxyethenyl)-(453537-15-0)

Safety Data

• Hazardous Substances Data: 453537-15-0(Hazardous Substances Data)

Upstream product

• 111-34-2 -butyl vinyl ether 
• 1122-91-4 4-bromo-benzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 

Downstream Products

• 3457-45-2 p-formylacetophenone 

Relevant articles and documents

Hydrogen-bonding-promoted oxidative addition and regioselective arylation of olefins with aryl chlorides

The first, general, and highly efficient catalytic system that allows a wide range of activated and unactivated aryl chlorides to couple regioselectively with olefins has been developed. The Heck arylation reaction is likely to be controlled by the oxidative addition of ArCl to Pd(0). Hence, an electron-rich diphosphine, 4-MeO-dppp, was introduced to facilitate the catalysis. Solvent choice is critical, however; only sluggish arylation is observed in DMF or DMSO, whereas the reaction proceeds well in ethylene glycol at 0.1-1 mol % catalyst loadings, displaying excellent regioselectivity. Mechanistic evidence supports that the arylation is turnover-limited by the oxidative addition step and, most importantly, that the oxidative addition is accelerated by ethylene glycol, most likely via hydrogen bonding to the chloride at the transition state as shown by DFT calculations. Ethylene glycol thus plays a double role in the arylation, facilitating oxidative addition and promoting the subsequent dissociation of chloride from Pd(II) to give a cationic Pd(II)-olefin species, which is key to the regioselectivity observed.

The Heck reaction of electron-rich olefins with regiocontrol by hydrogen-bond donors

No salt please: Halide scavengers AgOTf and TlOAc are not required for the Heck coupling of electron-rich olefins with aryl bromides and chlorides. Using ammonium additives, these reactions can be carried out in either an imidazolium ionic liquid or a common molecular solvent, thus furnishing 1,1′- disubstituted olefins in high yields with excellent regioselectivities. (Chemical Equation Presented).

A new efficient tetraphosphine/palladium catalyst for the Heck reaction of aryl halides with styrene or vinylether derivatives

cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C 3H5)]2 system efficiently catalyses the Heck reaction of aryl halides with styrene and vinylether derivatives. High turnover numbers can be obtained for the reaction of several aryl halides with styrene and styrene derivatives. Lower turnover numbers have been observed in the presence of vinylethers.