24131-32-6

Usage

Uses

Used in Organic Synthesis:
3,5-BIS(BENZYLOXY)BENZYL BROMIDE is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds, which are crucial in constructing complex organic molecules and frameworks.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 3,5-BIS(BENZYLOXY)BENZYL BROMIDE is used as a key building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Fine Chemicals Production:
3,5-BIS(BENZYLOXY)BENZYL BROMIDE is also utilized in the production of fine chemicals, where its unique structure and reactivity are harnessed to create specialty chemicals for various applications.
Used in Palladium-Catalyzed Cross-Coupling Reactions:
3,5-BIS(BENZYLOXY)BENZYL BROMIDE is employed as a reactant in palladium-catalyzed cross-coupling reactions, a significant method in modern organic chemistry for forming carbon-carbon bonds, which is essential for the synthesis of complex organic molecules and advanced materials.

InChI:InChI=1/C21H19BrO2/c22-14-19-11-20(23-15-17-7-3-1-4-8-17)13-21(12-19)24-16-18-9-5-2-6-10-18/h1-13H,14-16H2

Upstream product

• 24131-31-5 3,5-dibenzyloxybenzyl alcohol 
• 80457-61-0 methanesulfonyl 3,5-dibenzyloxybenzyl alcohol 
• 29654-55-5 5-(hydroxymethyl)benzene-1,3-diol 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 28917-43-3 3,5-dibenzyloxybenzoic acid 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 58605-10-0 methyl 3,5-bis(benzyloxy)benzoate 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 50513-72-9 (3,5-di-benzyloxy)benzoic acid benzyl ester 

Downstream Products

• 129835-71-8 3-(3,5-Bis-benzyloxy-benzyloxy)-5-hydroxymethyl-phenol 
• 156666-23-8 rac-3-(Benzyloxy)-1-<<3,5-bis(benzyloxy)benzyl>oxy>-2-<<(tert-butyldimethylsilyl)oxy>methyl>-2-<<(2-methoxyethoxy)methoxy>methyl>propane 
• 137472-16-3 [3,5-bis[[3,5-bis[[3,5-bis(phenylmethoxy)phenyl]methoxy]phenyl]methoxy]phenyl]methyl alcohol 
• 185413-77-8 1-(3,5-Bis-benzyloxy-phenyl)-2-methyl-heptane-3,5-dione 
• 137472-18-5 3,5-bis(3,5-bis(benzyloxy)benzyloxy)benzaldehyde 
• 210036-17-2 6,6'-Bis-(3,5-bis-benzyloxy-benzyloxy)-2,2'-bis-triisopropylsilanyloxy-[1,1']binaphthalenyl 
• 239447-26-8 4,4'-bis[3'',5''-bis(benzyloxy)phenylethyl]-2,2'-bipyridine 
• 259684-89-4 methyl 2,6-bis(3,5-dibenzyloxy-benzyloxy)benzoate 
• 255827-61-3 {4-[(2S,3R)-3-(3,5-Bis-benzyloxy-benzyloxy)-2-(3,5-bis-benzyloxy-benzyloxymethyl)-butyl]-benzyloxy}-tert-butyl-diphenyl-silane 

Relevant academic research and scientific papers

First example of a diazepinoporphyrazine with dendrimeric substituents

The synthesis and physicochemical properties of a novel diazepinoporphyrazine possessing G1-dendrimeric substituents are presented. Initially, diaminomaleonitrile was condensed with 1,3-bis-(4-hydroxyphenyl)-1,3-propanedione to give a novel 1,4-diazepine-

Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers

A simple method for the dimerization of phenylpropenoid derivatives is reported. It leverages electrochemical oxidation of p-unsaturated phenols to access the dimeric materials in a biomimetic fashion. The mild nature of the transformation provides excellent functional group tolerance, resulting in a unified approach for the synthesis of a range of natural products and related analogues with excellent regiocontrol. The operational simplicity of the method allows for greater efficiency in the synthesis of complex natural products. Interestingly, the quinone methide dimer intermediates are potent radical-trapping antioxidants; more so than the phenols from which they are derived—or transformed to—despite the fact that they do not possess a labile H-atom for transfer to the peroxyl radicals that propagate autoxidation.

NOVEL FUNCTIONALIZED 1,3-BENZENE DIOLS AND THEIR METHOD OF USE FOR THE TREATMENT OF HEPATIC ENCEPHALOPTHY

Pharmaceutical compositions of the invention include novel functionalized 1,3-benzenediols having a disease-modifying action in the treatment of hepatic encephalopathy and related conditions. Pharmaceutical compositions of the invention further include novel neuroprotective agents.

Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability

Cannabidiol is the nonpsychoactive natural component of C. sativa that has been shown to be neuroprotective in multiple animal models. Our interest is to advance a therapeutic candidate for the orphan indication hepatic encephalopathy (HE). HE is a serious neurological disorder that occurs in patients with cirrhosis or liver failure. Although cannabidiol is effective in models of HE, it has limitations in terms of safety and oral bioavailability. Herein, we describe a series of side chain modified resorcinols that were designed for greater hydrophilicity and "drug likeness", while varying hydrogen bond donors, acceptors, architecture, basicity, neutrality, acidity, and polar surface area within the pendent group. Our primary screen evaluated the ability of the test agents to prevent damage to hippocampal neurons induced by ammonium acetate and ethanol at clinically relevant concentrations. Notably, KLS-13019 was 50-fold more potent and >400-fold safer than cannabidiol and exhibited an in vitro profile consistent with improved oral bioavailability.

NOVEL FUNCTIONALIZED 1,3-BENZENE DIOLS AND THEIR METHOD OF USE FOR THE TREATMENT OF HEPATIC ENCEPHALOPATHY

Pharmaceutical compositions of the invention include novel functionalized 1,3-benzenediols having a disease-modifying action in the treatment of hepatic encephalopathy and related conditions. Pharmaceutical compositions of the invention further include novel neuroprotective agents.

Effect of the bulkiness of the end functional amide groups on the optical, gelation, and morphological properties of oligo(p-phenylenevinylene) π-gelators

Herein, we describe the role of end functional groups in the self-assembly of amide-functionalized oligo(p-phenylenevinylene) (OPV) gelators with different end-groups. The interplay between hydrogen-bonding and π-stacking interactions was controlled by the bulkiness of the end functional groups, thereby resulting in aggregates of different types, which led to the gelation of a wide range of solvents. The variable-temperature UV/Vis absorption and fluorescence spectroscopic features of gelators with small end-groups revealed the formation of 1D H-type aggregates in CHCl3. However, under fast cooling in toluene, 1D H-type aggregates were formed, whereas slow cooling resulted in 2D H-type aggregates. OPV amide with bulky dendritic end-group formed hydrogen-bonded random aggregates in toluene and a morphology transition from vesicles into fibrous aggregates was observed in THF. Interestingly, the presence of bulky end-group enhanced fluorescence in the xerogel state and aggregation in polar solvents. The difference between the aggregation properties of OPV amides with small and bulky end-groups allowed the preparation of self-assembled structures with distinct morphological and optical features. Buying in bulk: OPV amides with small end-groups self-assemble into 2D/1D aggregates in toluene and 1D aggregates in CHCl3. Bulky end-groups impede fluorescence quenching in the self-assembled state by blocking π-stacking and facilitate morphological transition in THF.

A detailed investigation of light-harvesting efficiency of blue color emitting divergent iridium dendrimers with peripheral phenylcarbazole units

The increase in phosphorescence efficiency was estimated by the energy transfer mechanism for divergent iridium dendrimers with peripheral phenylcarbazole units. A series of Ir-core/phenylcarbazole-end dendrons of the type, Ir(dfppy)2(pic-Czsu

Iridium-catalyzed dehydrogenative decarbonylation of primary alcohols with the liberation of syngas

A new iridium-catalyzed reaction in which molecular hydrogen and carbon monoxide are cleaved from primary alcohols in the absence of any stoichiometric additives has been developed. The dehydrogenative decarbonylation was achieved with a catalyst generated in situ from [Ir(coe)2Cl]2 (coe=cyclooctene) and racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (rac-BINAP) in a mesitylene solution saturated with water. A catalytic amount of lithium chloride was also added to improve the catalyst turnover. The reaction has been applied to a variety of primary alcohols and gives rise to products in good to excellent yields. Ethers, esters, imides, and aryl halides are stable under the reaction conditions, whereas olefins are partially saturated. The reaction is believed to proceed by two consecutive organometallic transformations that are catalyzed by the same iridium(I)-BINAP species. First, dehydrogenation of the primary alcohol to the corresponding aldehyde takes place, which is then followed by decarbonylation to the product with one less carbon atom.

Dimerization of piceatannol by Momordica charantia peroxidase and α-glucosidase inhibitory activity of the biotransformation products

Stilbenes, especially those oligomers, have great potential to be antihyperglycemic agents. In this study, eight stilbene dimers, including five new ones, were obtained by biotransformation of piceatannol using Momordica charantia peroxidase (MCP) for the first time. Their structures were established on the basis of spectroscopic evidences. These piceatannol dimers displayed potential α-glucosidase inhibitory activities, and trans double bond, tetrahydrofuran ring, and free adjacent phenolic dihydroxyls were found to be important for their activities. Enzymatic biotransformation of stilbenes by M. charantia peroxidase (MCP) was showed to be a prominent way to produce oligomeric stilbenes for antihyperglycemic development.

Chemical synthesis and evaluation of 17α-alkylated derivatives of estradiol as inhibitors of steroid sulfatase

Steroid sulfatase (STS) controls the levels of 3-hydroxysteroids available from circulating steroid sulfates in several normal and malignant tissues. This and the known involvement of active estrogens and androgens in diseases such as breast and prostate cancers thus make STS an interesting therapeutic target. Here we describe the chemical synthesis and characterization of an extended series of 17α-derivatives of estradiol (E2) using different strategies. A variant of the samarium-Barbier reaction with stoichiometric samarium metal and catalytic Kagan reagent formation was used for introducing low reactive benzyl substrates in position 17 of estrone (E1) whereas heterocyclic substrates were metalated and reacted with either the carbonyl or the 17-oxirane of E1. In vitro evaluation of the inhibitory potency of the new compounds against STS identified new inhibitors and allowed a more complete structure-activity relationship study of this family of 17α-derivatives of E2.