2041-21-6

Usage

Physical state

White solid

Usage

Production of various chemicals and pharmaceuticals

Precursor for

Synthesis of primary aromatic amines

Reagent for

Formation of C-N bonds in organic chemistry

Known for

Use in Gabriel synthesis (method for preparation of primary amines from alkyl halides)

Studied for

Potential biological activities, including antifungal and anticancer properties.

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 90-99-3 diphenylchloromethane 
• 101-81-5 Diphenylmethane 
• 776-74-9 Bromodiphenylmethane 
• 91-01-0 1,1-Diphenylmethanol 

Downstream Products

• 1782-38-3 O-(diphenylmethyl)hydroxylamine 
• 333363-89-6 4-[((2-diphenylmethoxy)amino)methyl]-1-[(4-fluorophenyl)methyl]piperidine 

Relevant academic research and scientific papers

Ultrasound accelerated synthesis of: O-alkylated hydroximides under solvent- A nd metal-free conditions

A novel, sustainable, environmentally friendly, high substrate scope, efficient, solvent-free and metal catalyst-free method for the cross-dehydrogenative coupling (CDC) reaction between N-hydroxyphthalimide (NHPI) and benzyl/ether compounds is described. This coupling reaction proceeds through ultrasound acceleration. Compared to conventional heating conditions, the use of ultrasound techniques not only improves the reaction efficiency and enhances the reaction rate but also minimizes the side reactions.

Organocatalytic Radical Involved Oxidative Cross-Coupling of N-Hydroxyphthalimide with Benzylic and Allylic Hydrocarbons

The cross-coupling reaction between N-hydroxyphthalimide and various benzylic and allylic hydrocarbons was realized through an organocatalytic radical-mediated process involving C(sp3)-O bond formation using tert-butyl hydroperoxide (t-BuOOH) as an oxidant and tetra-n-butylammonium iodide [(n-Bu]4NI] as a catalyst, during which the phthalimide N-oxyl (PINO) radical and benzylic and allylic radicals were generated in situ and underwent the selective radical/radical cross-coupling reaction. This novel method provides a convenient metal-free approach to the synthesis of O-alkylated hydroxy imides under mild reaction conditions.

Catalytic ortho -acetoxylation of masked benzyl alcohols via an exo -directing mode

A Pd-catalyzed ortho-acetoxylation of masked benzyl alcohols to synthesize various 2-hydroxyalkylphenol derivatives is reported. The 2,6-dimethoxyl benzaldoxime proved to be an efficient exo-type directing group for arene (sp2) C-H functionalization. Two strategies were demonstrated to remove the directing group through N-O and C-O bond cleavages. A high catalyst turnover (>1000) was obtained to illustrate the practicality of this method.

First acid-catalyzed entry to O-alkylated hydroximides from benzylic alcohols

A facile method for the synthesis of O-alkylated hydroximides through the acid-catalyzed alkylation of hydroximides by using benzylic alcohols as alkylating agents is described for the first time. The obtained O-propargylated products offered easy access

2-[(arylmethoxy)imino]imidazolidines with potential biological activities

A series of 2-[(arylmethoxy)imino]imidazolidines was synthesized by reacting 2-chloro-4,5-dihydroimidazole with corresponding O- arylmethylhydroxylamines and evaluated for their α1-, α2-adrenergic and imidazoline I1, I2 receptor binding affinities. The most potent 2-[(naphthalen-1-ylmethoxy)imino] imidazolidine showed a high selectivity and good affinity for the [ 3H]prazosin-labeled α1-adrenoceptors (Ki = 107 nM). Representative compounds of this series were also tested in vivo for possible circulatory effects in rats after intravenous administration.

Cu-facilitated C-O bond formation using N-hydroxyphthalimide: Efficient and selective functionalization of benzyl and allylic C-H bonds

A highly efficient protocol for the benzyl or allylic C-H functionalization of simple hydrocarbons has been developed using stoichiometric amounts of N-hydroxyphthalimide and PhI(OAc)2 in the presence of CuCl catalyst. The reaction was revealed to proceed via a radical pathway, in which phthalimide N-oxyl (PINO) radical plays a dual role, serving as a catalytic hydrogen abstractor from hydrocarbons as well as a stoichiometric reagent to couple with the resultant alkyl radicals. Copyright

N-and o-substituted 4-[2-( diphenylmethoxy) -ethyl]-1- (phenyl) methyl) piperidine analogs and methods of treating cns disorders therewith

N- and O-substituted 4[2-diaromaticmethoxy and methylamino)alkyl]piperidines exhibit high CNS activity with respect to the dopamine transporter (DAT) and serotonin transporter (SERT). Preferred compounds exhibit highly differential behavior as between the

Structure - Activity relationship studies of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine derivatives and their N-analogues: Evaluation of behavioral activity of O- and N-analogues and their binding to monoamine transporters

In our effort to develop a pharmacotherapy for the treatment of cocaine addiction, we embarked on synthesizing novel molecules targeting the dopamine transporter (DAT) molecule in the brain as DAT has been implicated strongly in the reinforcing effect of

Factors Affecting the Stability and Equilibria of Free Radicals. XIII. N-Alkoxy- and N-Aralkoxypicrylamines and ESR Spectra of the Corresponding Capto-Dative Persistent Aminyls

Five O-alkylhydroxylamines and three aralkylhydroxylamines have been picrylated to give O-alkyl-N-picrylhydroxylamines.These were converted to the corresponding N-(ar)alkoxy-picryl-aminyl radicals in toluene solution, and the ESR spectra were recorded.Simulations of the spectra with reasonable parameters and g values confirm the expected radical structures.Hyperfine coupling constants for nuclei in the picryl (acceptor) ring are smaller than those for the (ar)alkoxy group.This indication of competitive electron pair delocalization to the picryl ring, together with the long lifetimes of these radicals (compared with the symmetrically substituted diphenylaminyls), both support the concept of captodative stabilization.