1243-97-6

Usage

Uses

Used in Organic Synthesis:
BENZYLTRIPHENYLPHOSPHONIUM IODIDE is used as a phase-transfer catalyst for facilitating reactions that involve the transfer of nucleophilic anions from an aqueous phase to an organic phase. This application is crucial for achieving efficient and selective synthesis of a wide range of organic compounds.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, BENZYLTRIPHENYLPHOSPHONIUM IODIDE is utilized as a transfer reagent in the synthesis of various organic and pharmaceutical compounds. Its ability to act as a catalyst in phase-transfer reactions is particularly valuable for the production of complex molecules that require precise synthetic routes.
Used in Research Laboratories:
BENZYLTRIPHENYLPHOSPHONIUM IODIDE is also used in research settings as a versatile reagent for exploring new reaction pathways and developing innovative synthetic methods. Its role in enhancing the understanding of phase-transfer catalysis and its applications in organic chemistry is significant for advancing scientific knowledge in this domain.

InChI:InChI=1/C25H22P.HI/c1-5-13-22(14-6-1)21-26(23-15-7-2-8-16-23,24-17-9-3-10-18-24)25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1

Upstream product

• 620-05-3 iodomethylbenzene 
• 603-35-0 triphenylphosphine 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 4885-02-3 Dichloromethyl methyl ether 
• 16666-80-1 triphenylphosphonio-1-methylethanide 
• 16666-79-8 hexylidenetriphenylphosphoran 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 1754-88-7 ethylenetriphenylphosphorane 
• 91-14-5 1,2-divinylbenzene 
• 100-44-7 benzyl chloride 

Downstream Products

• 136409-28-4 N-<1-(4-Chlorphenyl)-2-phenylvinyl>iminotriphenylphosphoran 
• 154420-89-0 <<1-(2-Naphthyl)-2-phenylvinyl>imino>triphenylphosphoran 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 154420-90-3 <<1-(4-Methylphenyl)-2-phenylvinyl>imino>triphenylphosphoran 
• 166985-96-2 1,1,1,4-tetraphenyl-3-(2-pyridinyl)-2-aza-1,λ⁵-phosphabuta-1,3-diene 
• 185623-65-8 1,1,1,4-tetraphenyl-3-(2-thienyl)-2-aza-1,λ⁵-phosphabuta-1,3-diene 
• 185623-68-1 1,1,1,4-tetraphenyl-3-(3-pyridyl)-2-aza-1,λ⁵-phosphabuta-1,3-diene 
• 645-49-8 cis-stilben 
• 139308-79-5 1-Methanesulfonyl-4-((E)-styryl)-benzene 
• 722498-33-1 (3E)-3-trifluoromethyl-1,1,1,4-tetraphenyl-2-aza-1λ⁵-phosphabuta-1,3-diene 
• 722498-34-2 (3E)-3-perfluoroheptyl-1,1,1,4-tetraphenyl-2-aza-1λ⁵-phosphabuta-1,3-diene 
• 850582-44-4 (3E)-3-perfluoroethyl-1,1,1,4-tetraphenyl-2-aza-1λ⁵-phosphabuta-1,3-diene 
• 154420-92-5 N-(4-Chlorphenyl)-N'-<1-(2-naphthyl)-2-phenylvinyl>carbodiimid 
• 154420-97-0 N,N'-Bis<1-(4-methylphenyl)-2-phenylvinyl>carbodiimid 

Relevant academic research and scientific papers

Ionic Liquids as Solvents for SN2 Processes. Demonstration of the Complex Interplay of Interactions Resulting in the Observed Solvent Effects

Bimolecular nucleophilic substitution reactions between triphenylphosphine and benzylic electrophiles have been examined in an ionic liquid to probe interactions with species along the reaction coordinate. Trends in the rate constant were found on both varying the leaving group and the electronic nature of the aromatic ring. In all the cases considered, interactions between the components of the ionic liquid and the transition state were shown to be more significant in determining reaction outcome than previously observed for this class of reaction. This demonstrates the importance of considering interactions of the ionic liquid components with all species along the reaction coordinate when investigating the origin of ionic liquid solvent effects, along with how such effects might be exploited.

Production of cyclic carbonate

The purpose of the present invention is to provide a practical method for producing a cyclic carbonate, which is widely used for various applications such as electrolytic solutions for lithium-ion secondary batteries and plastic materials, by a reaction between an epoxide (oxirane) and carbon dioxide, the method giving consideration to the reduction of environmental loads and making it possible to produce said cyclic carbonate with high yield under mild conditions, such as at room temperature and atmospheric pressure. The present invention relates to a method for producing a cyclic carbonate, the method being characterized by reacting an epoxide and carbon dioxide in the presence of an iodine-anion-containing phosphonium salt including a hydrogen atom that can form a hydrogen bond with an oxygen atom in the epoxide.

Development of novel tail-modified anandamide analogs

To explore the hydrophobic groove subsite within the CB1 cannabinoid receptor we have designed and synthesized a group of tail-substituted anandamide analogs. Our design involves the introduction of aryl or heterocyclic ring as terminal substituents that

A Dynamic Equilibrium of Oxaphosphetanes

The course of the Wittig reaction was investigated by rapid injection NMR spectroscopy.Rate constants for the formation of oxaphosphetanes were determined.A new dynamic equilibrium of oxaphosphetanes was observed for the first time.The solvent and substituent dependence of the new effect was investigated.By labeling various oxaphosphetanes with 13C and 17O the lithium salt dependence of the new equilibrium was shown.A lithium adduct of oxaphosphetanes under these conditions is proposed. - Key Words: Wittig reaction / Rapid injection NMR / Dynamic NMR / Oxaphosphetanes

Photolysis of (Arylmethyl)triphenylphosphonium Salts. Substituent, Counterion, and Solvent Effects on Reaction Products

Quaternary (arylmethyl)phosphonium salts of the general formula ArCH2-PR3(+)Y(-) (Ar = substituted phenyl or 1-naphthyl; R = phenyl, ferrocenyl, or butyl; Y(-) = BF4(-) or halide) have been photolyzed in acetonitrile or in methanol.Photolysis involved the cleavage of the P-CH2 bond and the products derived from both, the arylmethyl radical and the carbocation, were formed.The proportion of the radical- and carbocation-derived products was determined as a function of substituents in group Ar, of groups R, counterions Y(-), and the solvent.For the nonoxidizable counterion (BF4(-), the proposed mechanism of the reaction involves initial homolysis, followed by the escape of the radical products from a solvent cage, or by the electron transfer from carbon to phosphorus, yielding the corresponding arylmethyl carbocation.The latter can either react with the solvent to form the observed carbocation-derived product or can undergo recombination with the tertiary phosphine formed to yield the starting phosphonium ion.Some indication of the "inverted substituent effect" resulting from the inhibition of single electron transfer from an easily oxidized radical was obtained.For the oxidizable counterions (halides), an additional pathway is suggested, that involves electron transfer from the anion, yielding the arylmethyl radical and the phosphine, thus decreasing the ionic/radical products ratio.

Organoboron Compounds, I. - Transformation of Phosphonium Ylides into Phosphane Monoalkylborane Complexes. - Hydroboration Reactions

Triphenylphosphonium ylides 1 add borane (from 2) with formation of alkylidenetriphenylphosphorane-boranes 3, which rearrange on heating to give the triphenylphosphane-monoalkylborane adducts 6.Compounds 6 can undergo hydroboration reactions.