26104-68-7

Usage

Uses

Used in Organic Synthesis:
(4-CYANOBENZYL)(TRIPHENYL)PHOSPHONIUM BROMIDE is used as a reagent for the synthesis of pharmaceuticals and organic molecules, making it a valuable tool in chemical research and development.
Used in Phase Transfer Catalysis:
(4-CYANOBENZYL)(TRIPHENYL)PHOSPHONIUM BROMIDE is used as a phase transfer catalyst to facilitate the transfer of reactants between immiscible phases such as aqueous and organic solvents, enhancing the efficiency of various chemical reactions.
Used in the Synthesis of Heterocycles:
(4-CYANOBENZYL)(TRIPHENYL)PHOSPHONIUM BROMIDE is used as a reagent in the synthesis of heterocycles and other organic compounds, contributing to the development of new chemical entities and materials.

Upstream product

• 104-85-8 para-methylbenzonitrile 
• 603-35-0 triphenylphosphine 
• 17201-43-3 4-cyanobenzyl bromide 

Downstream Products

• 37985-14-1 4-((1E,3E)-4-phenylbuta-1,3-dien-1-yl)benzonitrile 
• 2844-17-9 4-(dimethylamino)-4'-cyanostilbene 
• 128587-61-1 4-((E)-2-Furan-2-yl-vinyl)-benzonitrile 
• 89302-78-3 4-(propa-1,2-dienyl)benzonitrile 
• 141544-87-8 (E,E)-1-(4-cyanophenyl)-4-(4-hexyloxyphenyl)buta-1,3-diene 
• 4381-02-6 1,2-bis-(4-cyanophenyl)ethane 
• 791-28-6 Triphenylphosphine oxide 
• 5216-37-5 (E)-4,4'-dicyanostilbene 
• 185411-99-8 4-[(E)-2-(4-Trimethylsilanyl-phenyl)-vinyl]-benzonitrile 
• 2510-73-8 cis-4,4'-dicyanostilbene 
• 1552-40-5 1-(4-cyanophenyl)-4-phenyl-1,3-butadiene 

Relevant academic research and scientific papers

Comparison between organic sensitizers containing stilbene and azo group as bridging unit for dye sensitized solar cells

While azo dyes have been widely used in dye industry, the azo dyes have been seldom applied as sensitizers to dye sensitized solar cells. In this study, new metal-free organic sensitizers, ST and AZ, which are same structures except bridging units, were synthesized and evaluated. ST containing stilbene as bridging unit gave higher energy conversion efficiency than AZ containing azo group as bridging unit. As a result of density functional theory (DFT) calculations, ST displayed more localized frontier molecular orbitals at lowest unoccupied molecular orbital (LUMO) states than AZ.

Reactions of benzyltriphenylphosphonium salts under photoredox catalysis

The development of benzyltriphenylphosphonium salts as alkyl radical precursors using photoredox catalysis is described. Depending on substituents, the benzylic radicals may couple to form C-C bonds or abstract a hydrogen atom to form C-H bonds. A natural product, brittonin A, was also synthesized using this method.

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.

One-Step Synthesis of Substituted Benzofurans from ortho- Alkenylphenols via Palladium-Catalyzed C=H Functionalization

A dehydrogenative oxygenation of C(sp2)=H bonds with intramolecular phenolic hydroxy groups has been developed, which provides a straightforward and concise access to structurally diversely benzofurans from ortho-alkenylphenols. The reaction is catalyzed by palladium on carbon (Pd/C) without any oxidants and sacrificing hydrogen acceptors.

Styrylphenylphthalimides as Novel Transrepression-Selective Liver X Receptor (LXR) Modulators

Anti-inflammatory effects of liver X receptor (LXR) ligands are thought to be largely due to LXR-mediated transrepression, whereas side effects are caused by activation of LXR-responsive gene expression (transactivation). Therefore, selective LXR modulators that preferentially exhibit transrepression activity should exhibit anti-inflammatory properties with fewer side effects. Here, we synthesized a series of styrylphenylphthalimide analogues and evaluated their structure-activity relationships focusing on LXRs-transactivating-agonistic/antagonistic activities and transrepressional activity. Among the compounds examined, 17l showed potent LXR-transrepressional activity with high selectivity over transactivating activity and did not show characteristic side effects of LXR-transactivating agonists in cells. This representative compound, 17l, was confirmed to have LXR-dependent transrepressional activity and to bind directly to LXRβ. Compound 17l should be useful not only as a chemical tool for studying the biological functions of LXRs transrepression but also as a candidate for a safer agent to treat inflammatory diseases.

Catalytic, oxidant-free, direct olefination of alcohols using Wittig reagents

Reported here is the catalytic, acceptorless coupling of alcohols with in situ generated, non-stabilized phosphonium ylides to form olefins as major products. The reaction uses low catalyst loadings and does not require added oxidants. Hydrogenation of the product is minimized and the reaction leads to Z (aliphatic) or E (benzylic) stereospecificity.

Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs

A series of six/five member (E/Z)-Goniothalamin analogs were synthesized from commercially available (3,4-dihydro-2H-pyran-2-yl)methanol/5- (hydroxymethyl)dihydrofuran-2(3H)-one in three steps with good to moderate overall yields and their cytotoxicity against lymphoblastic leukemic T cell line (Jurkat E6.1) have been evaluated. Among the synthesized analogs, (Z)-Goniothalamin appeared to be the most active in cytotoxicity (IC 50 = 12 μM). Structure-activity relationship study indicates that introducing substituent in phenyl ring or replacing phenyl ring by pyridine/naphthalene, or decreasing the ring size of lactones (from six to five member) do not increase the cytotoxicity.

Chromo-fluorogenic detection of nerve-agent mimics using triggered cyclization reactions in push-pull dyes

A family of azo and stilbene derivatives (1-9) are synthesized, and their chromo-fluorogenic behavior in the presence of nerve-agent simulants, diethylchlorophosphate (DCP), diisopropylfluorophosphate (DFP), and diethylcyanophosphate (DCNP) in acetonitrile and mixed solution of water/acetonitrile (3:1 v/v) buffered at pH 5.6 with MES, is investigated. The prepared compounds contain 2-(2-N,N-dimethylaminophenyl) ethanol or 2-[(2-N,N-dimethylamino)phenoxy]ethanol reactive groups, which are part of the conjugated π-system of the dyes and are able to give acylation reactions with phosphonate substrates followed by a rapid intramolecular N-alkylation. The nerve-agent mimic-triggered cyclization reaction transforms a dimethylamino group into a quaternary ammonium, inducing a change of the electronic properties of the delocalized systems that results in a hypsochromic shift of the absorption band of the dyes. Similar reactivity studies are also carried out with other "non-toxic" organophosphorus compounds, but no changes in the UV/Vis spectra were observed. The emission behaviour of the reagents in acetonitrile and water-acetonitrile 3:1 v/v mixtures is also studied in the presence of nerve-agent simulants and other organophosphorous derivatives. The reactivity between 1-9 and DCP, DCNP, or DFP in buffered water-acetonitrile 3:1 v/v solutions under pseudo first-order kinetic conditions, using an excess of the corresponding simulant, are studied in order to determine the rate constants (k) and the half-life times (t1/2=ln2/k) for the reaction. The detection limits in water/acetonitrile 3:1 v/v are also determined for 1-9 and DCP, DCNP, and DFP. Finally, the chromogenic detection of nerve agent simulants both in solution and in gas phase are tested using silica gel containing adsorbed compounds 1, 2, 3, 4, or 5 with fine results.

Second generation of 5-ethenylbenzofuroxan derivatives as inhibitors of Trypanosoma cruzi growth: Synthesis, biological evaluation, and structure-activity relationships

In vitro growth inhibitory activity of 21 new 5-ethenylbenzofuroxan derivatives against the protozoan parasite Trypanosoma cruzi, the causative agent of American trypanosomiasis, was studied. The designed compounds possess the previously described exigencies for optimal anti-parasite activity, the 5-ethenylbenzofuroxanyl moiety with different substituents. The synthetic key for preparing the derivatives was the Wittig procedure, that when 5-formylbenzofuroxan was used as the electrophile the corresponding deoxygenated products were marginally generated. Four of the new derivatives displayed remarkable in vitro activities against the epimastigote form of three strains of T. cruzi, Tulahuen 2, CL Brener, and Y. While the three deoxygenated analogues biologically assayed resulted inactives. Unspecific cytotoxicity was evaluated using human macrophages and active derivatives were not toxic at a concentration at least 13 times that of its IC50 against T. cruzi (CL Brener strain). From the preliminary structure-activity relationship studies lipophilicity and electronic requirements were found relevant to anti-T. cruzi activity. Active compounds are more lipophilic than inactive ones and it was also identified that an optimum value of R Swain-Lupton's descriptor is required for optimal activity.

Synthesis of novel sulfonyl-stabilized phosphorus ylides, and the kinetics and mechanism of their conventional and flash vacuum pyrolysis reactions

Nine substituted sulfonyl-stabilized phosphorus ylides were prepared by treating their intermediate ylide analogues with phenylmethanesulfonyl fluoride. The stoichiometric ratio of the reactants for each preparation needed to be adjusted according to the basicity of each ylide intermediate. The nine ylide compounds were then subjected to conventional (sealed-tube) gas-phase pyrolysis at 470-545 K. The pyrolytic reactions were homogeneous and obeyed a first-order rate equation. The values of the Arrhenius log A (s-1) and E a (kJ mol-1) obtained for these reactions averaged 11.12 ± 2.00 and 131.8 ± 24.4, respectively. Analysis of the pyrolysates from conventional pyrolysis and from flash vacuum pyrolysis at 600 K showed the products to be complex mixtures of triphenylphosphine, triphenylphosphine oxide, triphenylphosphine sulfide, and symmetric and unsymmetric alkenes. Conventional pyrolysis also gave novel mixed sulfones and, for the p-methoxyaryl substituent, p-anisaldehyde. The products of the reactions under study are explained on the basis of a mechanism involving a sulfonyl carbene intermediate, and the reaction mechanism is used to rationalize the kinetic results and molecular reactivities.