154318-72-6

Basic information

• Product Name: {2-[1-(4-Methoxy-phenyl)-vinyloxy]-ethyl}-dimethyl-amine
• Synonyms: {2-[1-(4-Methoxy-phenyl)-vinyloxy]-ethyl}-dimethyl-amine
• CAS NO: 154318-72-6
• Molecular Weight: 221.299
• Mol File: 154318-72-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: {2-[1-(4-Methoxy-phenyl)-vinyloxy]-ethyl}-dimethyl-amine(CAS DataBase Reference)
• NIST Chemistry Reference: {2-[1-(4-Methoxy-phenyl)-vinyloxy]-ethyl}-dimethyl-amine(154318-72-6)
• EPA Substance Registry System: {2-[1-(4-Methoxy-phenyl)-vinyloxy]-ethyl}-dimethyl-amine(154318-72-6)

Safety Data

• Hazardous Substances Data: 154318-72-6(Hazardous Substances Data)

Upstream product

• 3622-76-2 (2-ethenyloxyethyl)dimethylamine 
• 623-12-1 4-chloromethoxybenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 66107-29-7 4-methoxyphenyl triflate 

Downstream Products

• 61161-13-5 4'-methoxy-2,2-bis(p-methoxyphenyl)acetophenone 
• 1889-74-3 1-(4-methoxyphenyl)-2,2-diphenylethanone 
• 1027238-87-4 {2-[1-(4-methoxy-phenyl)-2,2-diphenyl-vinyloxy]-ethyl}-dimethyl-amine 

Relevant articles and documents

Selective terminal heck arylation of vinyl ethers with aryl chlorides: A combined experimental-computational approach including synthesis of betaxolol

Reaction conditions have been developed for palladium-catalyzed terminal (β-) arylation of acyclic vinyl ethers with high regioselectivity using inexpensive aryl chlorides as starting materials and the P(t-Bu)3 releasing preligand [(t-Bu3)PH]BF4 as the key additive. This swift and straightforward protocol exploits non-inert conditions and controlled microwave heating to minimize handling and processing times and uses aqueous DMF or environmentally friendly PEG-200 as the reaction medium. The selectivity for linear β-product in PEG-200 is slightly higher than in aqueous DMF. DFT calculations support a ligand-driven selectivity rationale, where the electronic and steric influence of bulky P(t-Bu)3 ligand provides improved β-selectivity in the essential insertion step also with electron-rich aryl chlorides. A tentative computational rationalization of the improved selectivity in non-methylated PEG is discussed. Finally the synthetic methodology was used to provide efficient access to linear p-[2- (cyclopropylmethoxy)-ethyl] phenol from p-nitrophenyl chloride, a key intermediate in the synthesis of the β-adrenergic blocking agent Betaxolol.

Chelation-Controlled, Palladium-Catalyzed Arylation of Enol Ethers with Aryl Triflates. Ligand Control of Selection for α- or β-Arylation of ethene

Palladium-catalyzed arylation reactions of ethene (1) with a series of aryl triflates were performed under a variety of reaction conditions.In particular, the influence of phosphine ligands and halide additives on regioselectivity were studied.It was found that the chelation-controlled arylation of 1 affords an expedient route for the conversion of phenols into arylacetaldehydes.Alternatively, the same starting materials could be used to synthesize acetophenones by reversing the regioselectivity with bidentate phosphine ligands.