2736-31-4

Upstream product

• 102101-50-8 (4-Chloro-benzyl)-dimethyl-trimethylsilanylmethyl-ammonium; chloride 
• 156-41-2 4-chlorophenylethylamine 
• 140-53-4 p-chlorobenzyl cyanide 
• 1875-88-3 2-(4-Chlorophenyl)ethanol 
• 124-40-3 dimethyl amine 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 

Relevant academic research and scientific papers

Dimethylamination of Primary Alcohols Using a Homogeneous Iridium Catalyst: A Synthetic Method for N, N-Dimethylamine Derivatives

A new catalytic system for N,N-dimethylamination of primary alcohols using aqueous dimethylamine in the absence of additional organic solvents has been developed. The reaction proceeds via borrowing hydrogen processes, which are atom-efficient and environmentally benign. An iridium catalyst bearing an N-heterocyclic carbene (NHC) ligand exhibited high performance, without showing any deactivation under aqueous conditions. In addition, valuable N,N-dimethylamine derivatives, including biologically active and pharmaceutical molecules, were synthesized. The practical application of this methodology was demonstrated by a gram-scale reaction.

Rearrangement of (Substituted benzyl)trimethylammonium Ylides in a Nonbasic Medium: The Improved Sommelet-Hauser Rearrangement

Benzyl quaternary ammonium ylide formation in a nonbasic medium was accomplished by fluoride anion induced desilylation of benzyldimethylammonium bromide (3a) and ortho- or para-substituted benzyl analogues 3b-k.Treatment of 3 with CsF in HMPA at room temperature gives high yields of the Sommelet-Hauser rearrangement products 7 from 3a and methyl-, acetoxy-, and chloro-substituted analogues 3b-f.However, formation of the Stevens rearrangement products 8 is competitive for the reaction of compounds 3g-k having strong electron-withdrawing substituents such as acetyl, cyano, and nitrogen groups.From the o-cyano-substituted analogue 3h, a considerable amount of para Sommelet-Hauser rearrangement product is isolated.

A Convenient Synthesis of o-Methylbenzylamine Derivatives from Benzyl Halides: The Improved Sommelet-Hauser Rearrangement

Desilylation by fluoride anion of benzyldimethyl(trimethylsislylmethyl)ammonium halides having a Cl(1-), CN(1-), or AcO(1-) substituent on the benzene ring gave high yields of the Sommelet-Hauser rearrangement products at room temperature.