1530-36-5

Usage

Chemical Properties

white powder

Uses

(2-Methylbenzyl)triphenylphosphonium Bromide is a Wittig reagent.

InChI:InChI=1/C26H24P.BrH/c1-22-13-11-12-14-23(22)21-27(24-15-5-2-6-16-24,25-17-7-3-8-18-25)26-19-9-4-10-20-26;/h2-20H,21H2,1H3;1H/q+1;/p-1

Upstream product

• 603-35-0 triphenylphosphine 
• 89-92-9 2-methylbenzyl bromide 
• 552-45-4 1-chloromethyl-2-methylbenzene 

Downstream Products

• 80663-23-6 cis-2,2',3-trimethylstilbene 
• 80663-24-7 trans-2,2',3-trimethylstilbene 
• 10311-74-7 2,2'-dimethyl-stilbene 
• 172796-30-4 1,3,5-Tris-((E)-2-o-tolyl-vinyl)-benzene 
• 61509-91-9 3-(α-Triphenylphosphoranyliden-2-methyl-benzyl)-4-phenyl-3-cyclobuten-1,2-dion 
• 174004-36-5 cis-2-(2-Methylstyryl)pyrrole 
• 174004-37-6 trans-2-(2-Methylstyryl)pyrrole 
• 2077-33-0 1-methyl-2-[(1Z)-prop-1-en-1-yl]benzene 
• 2077-34-1 (E)-1-(o-methylphenyl)-1-propene 
• 134749-76-1 Triphenyl-(1-o-tolylmethanesulfonyl-ethylidene)-λ⁵-phosphane 
• 67456-94-4 2-chloro-2'-methylstilbene 
• 62640-58-8 2-chloro-2'-methylstilbene 
• 5294-03-1 di-o-tolylethyne 
• 57542-62-8 4-Acetyl-2,2-dimethyldiphenylacetylen 

Relevant academic research and scientific papers

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.

Cyclic Ureas

Amides that inhibit cellular necrosis and/or human receptor interacting protein 1 kinase (RIP1), including corresponding sulfonamides, and pharmaceutically acceptable salts, hydrates and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof with an effective amount of the compound or composition, and detecting a resultant improvement in the person's health or condition.

COMPOUNDS FOR MODULATING DDAH AND ADMA LEVELS, AS WELL AS METHODS OF USING THEREOF TO TREAT DISEASE

Disclosed are compounds that can modulate DDAH and the amount of asymmetric dimethylarginine (ADMA) in a subject. Also provided are pharmaceutical compositions comprising these compounds, as well as methods of using these compositions to treat and/or prevent diseases associated with elevated or low levels of DDAH and ADMA.

Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes

A new simple and efficient method for the synthesis of 2-phenylnaphthalenes from electron-rich 1-styryl-2-methoxybenzenes has been described. The reaction proceeds via TFA catalyzed C-C bond cleavage followed by intermolecular [4+2]-Diels-Alder cycloaddition of an in situ formed styrenyl trifluoroacetate intermediate. The quantum chemical calculations identified the transition state for the cycloaddition reaction and helped in tracing the reaction mechanism. The method has been efficiently utilized for synthesis of the phenanthrene skeleton and a naphthalene-based potent and selective ER-β agonist. This journal is

A simple and efficient total synthesis of (±)-danshexinkun A, a bioactive diterpenoid from Salvia miltiorrhiza

An efficient 12-step route for the synthesis of the diterpenoid quinone (±)-danshexinkun A in 23% overall yield from the corresponding highly substituted stilbene using a photocyclization strategy is described.

Addition of ArSSAr to dienes via intramolecular C-C bond formation initiated by a catalytic amount of ArS+

A catalytic amount of electrochemically generated "ArS +" ("ArS+" = ArS(ArSSAr)+) initiates a cation chain reaction of dienes that involves the addition of ArSSAr associated with stereoselective intramolecular carbon-carbon bond formation, and the direct (in-cell) electrolysis of a mixture of a diene and ArSSAr with a catalytic amount of electricity also effectively initiates the reaction. The Royal Society of Chemistry 2009.

The synthesis of alkenes via epi-phosphonium species: 2. A phosphorus Ramberg-Backlund reaction

Stilbene may be synthesised with Z-selectivity from (α- bromobenzyl)benzyldiphenylphosphonium bromide by the action of amine bases. A series of stilbenes was synthesised by the action of N-bromosuccinimide and 2,2,6,6-tetramethylpiperidine directly upon dibenzyldiphenylphosphonium salts. The reaction, essentially a phosphonium analogue of the Ramberg- Backlund displays cis selectivity. The dibenzyldiphenylphosphonium salts were prepared by the one pot polymethylhydrosiloxane/titanium(IV) isopropoxide mediated reduction/alkylation of benzyldiphenylphosphine oxides.

Kinetic Study of the Substitution Reactions of Triphenylphosphine with Chlorobenzyl Chlorides, Dimethylbenzyl Chloride, and Methylbenzyl Bromides in Various Two-Phase Organic Solvent/Water Media

The kinetics of the substitution reactions of triphenylphosphine (TP) with chlorobenzyl chlorides (CBC), 2,5-dimethylbenzyl chloride (DMBC), and methylbenzyl bromides (MBB) in aprotic organic solvent was studied under the extraction by water. The effects of water, agitation, organic solvent, reactant, and temperature were investigated. These reactions take place via the SN2 mechanism and exhibit large and negative entropy of activation. The order of relative activity of solvents is CHCl3 > CH2Cl2 >> C6H6. In CHCl3, the order of relative reactivity of benzyl chloride (BC), benzyl bromide (BB), CBC, DMBC, and MBB toward reaction with TP is 2-MBB > 4-MBB > 3-MBB > BB > DMBC > BC > 2-CBC > 4-CBC > 3-CBC. These reactions produce quantitatively benzyltriphenylphosphonium salts, which are useful for synthesizing Z-form isomers of stilbenes via the two-phase Wittig reaction.

Short synthetic approach towards the triindenotriphenylene (hemifullerene) system

A two-step synthesis of trimethyltribenzotriphenylene 2 from readily available starting materials involving three-fold Wittig reaction and three-fold oxidative photocyclization along a C3-symmetry path is reported.Flash vacuum pyrolysis of 2 in the quest for the triindenotriphenylene (hemifullerene) system has so far led only to the formation of mono-coupled products 6 and 7.

Heterodiene cycloadditoins of C2 symmetric 4,5-disubstituted ketene acetals: the nett asymmetric conjugate addition of recyclable acetic ester enolate equivalents to an activated enone

Heterodiene cycloadditions of 3-formylchromone 2 to a series of ketene acetals 1 derived from C2 symmetric 1,2-diarylethane-1,2-diols are diastereoselective.From (S,S)-1,2-di(o-tolyl)ethane-1,2-diol 6c the major cycloadduct 3c was isolated by crystallization and transformed by acid-catalysed methanolysis into (S)-methyl 4-oxo-3,4-dihydro-2H-1-benzopyran-2-ylacetate 5, together with the original 1,2-diol 6c which could be recycled.The structures of two cyclic carbonates 22a and 22c were determined by X-ray diffraction and used as models in seeking a mechanistic rationale for the stereoselective cycloadditions of the analogous ketene acetals 1a and 1c.