20600-22-0

Usage

Uses

Used in Pharmaceutical Industry:
1-Bromo-4-(phenoxymethyl)benzene is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 1-bromo-4-(phenoxymethyl)benzene is utilized as a precursor for the production of pesticides and other agrochemicals. Its versatility in organic synthesis contributes to the creation of effective solutions for agricultural challenges.
Safety Precautions:

Upstream product

• 873-75-6 4-bromobenzenemethanol 
• 66003-78-9 triphenylsulfonium trifluoromethanesulfonate 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 98-80-6 phenylboronic acid 
• 108-95-2 phenol 
• 55883-45-9 4-bromobenzyliodide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1122-91-4 4-bromo-benzaldehyde 
• 589-17-3 p-bromobenzyl chloride 
• 139-02-6 sodium phenoxide 

Downstream Products

• 1122-91-4 4-bromo-benzaldehyde 
• 108-95-2 phenol 
• 139-66-2 diphenyl sulfide 
• 94306-40-8 Phenyl-(4-phenylmercapto-benzyl)-sulfid 
• 946-80-5 (benzyloxy)benzene 
• 3699-01-2 4-tolyl phenyl sulfide 
• 75954-35-7 phenyl p-bromobenzyl sulfide 
• 1026753-32-1 rac-4-(Morpholin-4-yl)-2-(4-(phenoxymethyl)phenyl)butan-2-ol 
• 153227-19-1 3-(4-phenoxymethylphenyl)-quinuclidin-3-ol 
• 31719-76-3 4-phenoxymethyl-benzoic acid 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of pyrimidine analogs as SecA inhibitors

SecA, a key component of the bacterial Sec-dependent secretion pathway, is an attractive target for the development of new antimicrobial agents. We have previously reported pyrimidine analogs as SecA inhibitors. Herein, we report an extension of the earlier work in the synthesis and evaluation of a series of 15 5-cyanothiouracil derivatives as SecA inhibitors. All the compounds have been evaluated for their inhibition of SecA ATPase (EcSecAN68) and for their antimicrobial activity against Escherichia coli NR698 (a leaky mutant) and Bacillus anthracis Sterne. Twelve compounds showed IC50 of less than 6.3 μM when tested against EcSecAN68. In antimicrobial studies against E. coli NR698, six compounds showed MIC of 12.5 μM with three being less than 6.3 μM. Against B. anthracis Sterne, three compounds showed MIC of 6.3 μM.

An alternative route for boron phenoxide preparation from arylboronic acid and its application for C[sbnd]O bond formation

An efficient synthetic route to benzyl phenyl ether preparation has been successfully developed via a one-pot synthetic protocol utilizing a combination of arylboronic acids, hydrogen peroxide (H2O2), and benzyl halides. The whole procedure consists of two consecutive reactions, formation of boron phenoxide from arylboronic acids and its nucleophilic attack. A simple operation under mild conditions such as room-temperature ionic liquid (choline hydroxide), aerobic environment, and absence of metal- and base-catalysts has been employed. Expansion to utilize benzyl surrogates was also successfully accomplished.

Developing benign syntheses using ion pairsviasolvent-free mechanochemistry

Solvent-free mechanochemical conditions have been developed to investigate the significance of ion pairing and the use of weak bases for driving forward nucleophilic substitution reactions. This approach takes advantage of the lack of solvent shells to in

Choline Hydroxide as a Versatile Medium for Catalyst-Free O-Functionalization of Phenols

A versatile synthetic protocol for benzyl phenyl ether preparation via O-alkylation of phenolic oxygen with readily available benzyl derivatives was demonstrated. The newly designed procedure was carried out using an eco-friendly medium, room-temperature ionic liquid (choline hydroxide), under metal- and base-catalyst-free aerobic conditions. The reaction platform was also successfully applied to phenol protection strategy.

Base-Mediated O-Arylation of Alcohols and Phenols by Triarylsulfonium Triflates

A mild and efficient protocol for O-arylation of alcohols and phenols (ROH) by triarylsulfonium triflates was developed under transition-metal-free conditions. Various alcohols, including primary, secondary and tertiary, and phenols bearing either electron-donating or electron-withdrawing groups on the aryl rings were smoothly converted to form the corresponding aromatic ethers in moderate to excellent yields. The reactions were conducted at 50 or 80 °C for 24 h in the presence of a certain base and showed good functional group tolerance. The base-mediated arylation with asymmetric triarylsulfonium salts could selectively transfer the aryl groups of sulfoniums to ROH, depending on their inherent electronic nature. The mechanistic studies revealed that the reaction might proceed through the nucleophilic attack of the in situ formed alkoxy or phenoxy anions at the aromatic carbon atoms of the C?S bonds of triarylsulfonium cations to furnish the target products.

Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes

A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.

From insertion to multicomponent coupling: Temperature dependent reactions of arynes with aliphatic alcohols

The temperature dependent selectivity switch in the reaction of arynes with aliphatic alcohols in THF has been reported. At -20°C, arynes smoothly insert into the O-H bond of alcohols to form alkyl aryl ethers. Interestingly, at 60°C, a highly selective multicomponent coupling occurs with the solvent THF acting as the nucleophilic trigger affording (4-(alkoxy)butoxy)arenes.

NEW ARYLALKENYLPROPARGYLAMINE DERIVATIVES EXHIBITING NEUROPROTECTIVE ACTION FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

The invention relates to novel arylalkenylpropargylamine derivatives of general formula (I) or enantiomers or diastereomers thereof or salts, optionally pharmaceutically acceptable salts, or solvates of any of these. The compounds can be used in treating or preventing a disease or condition in a mammal related to monoamine oxidase dysfunction, especially in neurodegenerative diseases, e.g. Parkinson's disease, Alzheimer's disease or Huntington's disease.

Novel arylalkenylpropargylamines as neuroprotective, potent, and selective monoamine oxidase B inhibitors for the treatment of Parkinson's disease

To develop novel neuroprotective agents, a library of novel arylalkenylpropargylamines was synthesized and tested for inhibitory activities against monoamine oxidases. From this, a number of highly potent and selective monoamine oxidase B inhibitors were identified. Selected compounds were also tested for neuroprotection in in vitro studies with PC-12 cells treated with 6-OHDA and rotenone, respectively. It was observed that some of the compounds tested yielded a marked increase in survival in PC-12 cells treated with the neurotoxins. This indicates that these propargylamines are able to confer protection against the effects of the toxins and may also be considered as novel disease-modifying anti-Parkinsonian agents, which are much needed for the therapy of Parkinson's disease.

2-(HETERO)ARYL-BENZIMIDAZOLE AND IMIDAZOPYRIDINE DERIVATIVES AS INHIBITORS OF ASPARAGIME EMETHYL TRANSFERASE

Substituted benzimidazole and 3H-imidazo[4,5-b]pyridines or formula I: where X and Y respectively are selected from: (i) N and N; and (ii) N and CR4; A2 is selected from:, a C5 heteroarylene group, containing 2 or 3 ring heteroatoms, where the bonds to L1 and the core are β to one another; L1 is selected from: (i)A1-O-CH2-A2; (ii)A1-CH2-O-A2; (iii)A1-C(=O)-NH-A2; (iv)A1-CH(OH)-A2; (v)A1-CH2-NH-C(=O)-A2; (vi) A1-S-CH2-A2; (vii)A1- CH2-S-A2; (viii)A1-CH2-A2; and (ix)A1-CH(CH3)-O-A2; A1 is phenyl, optionally substituted by F or CF3; their use as pharmaceuticals, and in particular, in treating cancer and hemoglobinopathies.