1530-38-7

Basic information

• Product Name: (4-Methoxybenzyl)tris(phenyl)phosphonium bromide
• Synonyms: (4-Methoxybenzyl)tris(phenyl)phosphonium bromide
• CAS NO: 1530-38-7
• Molecular Formula: Br*C₂₆H₂₄OP
• Molecular Weight: 463.345921
• Mol File: 1530-38-7.mol
• Article Data: 40

Chemical Properties

• Melting Point: 226-228 °C
• Appearance: /
• CAS DataBase Reference: (4-Methoxybenzyl)tris(phenyl)phosphonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Methoxybenzyl)tris(phenyl)phosphonium bromide(1530-38-7)
• EPA Substance Registry System: (4-Methoxybenzyl)tris(phenyl)phosphonium bromide(1530-38-7)

Safety Data

• Hazardous Substances Data: 1530-38-7(Hazardous Substances Data)

Usage

General Description

"(4-Methoxybenzyl)tris(phenyl)phosphonium bromide" is a phosphonium salt that contains a 4-methoxybenzyl group and three phenyl groups attached to a phosphonium center with a bromide anion. It is commonly used as a phase transfer catalyst in organic synthesis reactions, where it facilitates the transfer of reactants between immiscible phases, such as between an aqueous and organic phase. (4-Methoxybenzyl)tris(phenyl)phosphonium bromide is known for its ability to promote efficient and selective reactions, making it a valuable tool in the synthesis of various organic compounds. Additionally, it has been studied for its potential antimicrobial properties, demonstrating promise as a novel antimicrobial agent for pharmaceutical and biomedical applications.

InChI:InChI=1/C26H24OP.BrH/c1-27-23-19-17-22(18-20-23)21-28(24-11-5-2-6-12-24,25-13-7-3-8-14-25)26-15-9-4-10-16-26;/h2-20H,21H2,1H3;1H/q+1;/p-1

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 603-35-0 triphenylphosphine 
• 104-93-8 p-methylanizole 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-13-5 4-Methoxybenzyl alcohol 
• 106-44-5 p-cresol 
• 6399-81-1 triphenylphosphine hydrobromide 
• 2746-25-0 p-Methoxybenzyl bromide 

Downstream Products

• 51848-93-2 [(benzylsulfonyl)(4-methoxyphenyl)methylene](triphenyl)phosphorane 
• 23833-69-4 1-[(Z)-2-(4-Methoxy-phenyl)-vinyl]-naphthalene 
• 15207-17-7 Triphenyl-<1,2-bis-(4-methoxyphenyl)-aethyl>-phosphoniumbromid 
• 18513-95-6 (E)-3,4,4'-trimethoxystilbene 
• 106053-26-3 (Z)-1-(4-methoxyphenyl)-2-(3,4-dimethoxyphenyl)ethene 
• 90047-93-1 cis-4-methoxy-β-(1-pyrenyl)styrene 
• 90047-91-9 trans-4-methoxy-β-(1-pyrenyl)styrene 
• 176325-26-1 3-(4-methoxyphenethenyl)-2,4,4-trimethyl-1-cyclohexene 
• 22145-08-0 (E,E)-1-(4-methoxyphenyl)-4-phenyl-1,3-butadiene 
• 259199-34-3 6-[2-(4-methoxy-phenyl)-vinyl]-naphthalene-2-carbonitrile 
• 205882-11-7 (E)-2-(4-methoxystyryl)furan 
• 223377-41-1 (E)-2-[2-(4-methoxylphenyl)ethenyl]thiophene 
• 299430-44-7 trans-3-(p-methoxystyryl)furan 
• 635678-36-3 cis-3-(p-methoxystyryl)furan 

Relevant articles and documents

A turn-on fluorescence probe for imaging iodide in living cells based on an elimination reaction

Based on a unique elimination reaction prompted by the iodide ion, a novel turn-on fluorescence probe (HCy-OMe-Br) has been developed for the first time. The probe emits in the near infrared region with a large Stokes shift, and can respond rapidly to iodide with high selectivity and sensitivity. This journal is

One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols

Two approaches for the synthesis of substituted phosphonium salts from easily available benzyl alcohols and their heterocyclic analogs have been developed. The developed protocols are complementary: the direct mixing of alcohol, trimethylsilyl bromide, and triphenylphosphine in 1,4-dioxane followed by heating at 80 °C was found to be more efficient for acid-sensitive substrates, such as salicyl or furfuryl alcohols as well as secondary benzyl alcohols, while a one-pot procedure including sequential addition of trimethylsilyl bromide and triphenylphosphine gave higher yields for benzyl alcohols bearing electroneutral or electron-withdrawing substituents.

Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters

A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.