1031-15-8

Usage

Uses

1. Synthetic Chemistry:
Methyl triphenyl phosphonium chloride is used as a phase transfer catalyst in synthetic chemistry. It facilitates the transfer of reactants between different phases, such as between an aqueous and an organic phase, thereby enhancing the efficiency of chemical reactions.
2. Polymerization:
In the field of polymer science, it acts as a catalyst for regio-controlled ring-opening polymerization of substituted epoxides. This application is crucial for the synthesis of polymers with specific structures and properties.
3. Corrosion Control:
Methyl triphenyl phosphonium chloride is utilized for controlling the corrosion of iron. It helps in preventing the degradation of iron and steel structures, which is essential for maintaining the integrity and longevity of various industrial equipment and infrastructure.
4. Intramolecular Nitrone Cycloaddition:
It acts as a reactant in intramolecular nitrone cycloaddition, a chemical reaction that is used to form complex molecular structures. This reaction is particularly useful in the synthesis of pharmaceutical compounds and other specialty chemicals.
5. Anticancer Applications:
Methyl triphenyl phosphonium chloride is used for neoplasm inhibition through its antimitochondrial effect. It has the potential to disrupt the function of mitochondria in cancer cells, thereby inhibiting their growth and proliferation.

InChI:InChI=1/C19H18P.ClH/c1-20(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19;/h2-16H,1H3;1H/q+1;/p-1

Upstream product

• 74-87-3 methylene chloride 
• 603-35-0 triphenylphosphine 
• 54446-70-7 trimethyl-methylenearsorane 
• 75-77-4 chloro-trimethyl-silane 
• 19493-09-5 Methylenetriphenylphosphorane 
• 712-48-1 chlorodiphenylarsine 
• 96254-26-1 Triphenylphosphonium-(diphenylarsino)methylid 
• 64723-81-5 <2-Phenyl-2-(phenylimino)ethyliden>triphenylphosphoran 
• 15424-14-3 N-phenylbenzohydrazonoyl chloride 
• 104438-92-8 <2-(4-Methoxyphenyl)-2-(phenylimino)ethyliden>triphenylphosphoran 
• 18147-18-7 tert-butyldichloromethylsilane 
• 18395-90-9 Di-tert-butyldichlorosilane 
• 1071-38-1 N,N,N',N'-Tetramethylformamidinium chloride 
• 4791-23-5 N-chloroacetyl-N'-phenylurea 

Downstream Products

• 16640-69-0 4-phenyl-1-(triphenylphosphoranylidene)butan-2-one 
• 1174-61-4 (Benzylcarbonylmethylene)triphenylphosphorane 
• 188999-31-7 5-methoxy-2-vinyl-4-azaindole 
• 40001-26-1 methyltriphenylphosphonium tetrahydroborate 
• 156441-18-8 (2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-vinylpyrrolidine 
• 257928-44-2 1-(benzyloxy)-4-(prop-1-en-2-yl)benzene 
• 915944-51-3 C₈H₄BrF₃ 
• 83299-46-1 methyltriphenylphosphonium tetrachloroferrate(III) 
• 10545-99-0 sulfur dichloride 
• 10025-87-3 trichlorophosphate 

Relevant academic research and scientific papers

Long sought synthesis of quaternary phosphonium salts from phosphine oxides: Inverse reactivity approach

Quaternary phosphonium salts (QPS), a key class of organophosphorus compounds, have previously only been available by routes involving nucleophilic phosphorus. We report the realisation of the opposite approach to QPS utilising phosphine oxides as the electrophilic partner and Grignard reagents as nucleophiles. The process is enabled through the crucial intermediacy of the derived halophosphonium salts. The route does not suffer from the slow kinetics and limited availability of many parent phosphines and a broad range of QPS were prepared in excellent yields.

METALLORGANISCHE VERBINDUNGEN DER LANTHANOIDE. X. BIS(η5-CYCLOPENTADIENYL)CHLOROLUTETINYLMETHYLENTRIPHENYLPHOSPHORAN: EIN ZWITTERIONISCHES METALLORGANYL DER LANTHANOIDENREIHE

Bis(η5-cyclopentadienyl)chlorolutetium reacts with methylenetriphenylphosphorane yielding a stable 1/1 complex, which was proved to be a zwitterionic organometallic compound having a Lu-CH2 ?-bond by NMR spectroscopy.

Exploring an Umpolung strategy for quaternization of phosphorus

We propose a new, potentially widely-applicable, Umpolung approach for the synthesis of quaternary phosphonium salts R3PR1 X (X = Cl, Br) from phosphine oxides R3PO. The new organic group R1 is introduced via nucleophilic attack on an intermediate halophosphonium salt using a Grignard reagent R1MgX and replaces the traditional phosphine quaternization approach. Consequently, the new method does not suffer from the limited availability of many parent phosphines and is much faster than standard quaternization.

Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides

Since the seminal work of Zhang in 2016, donor-acceptor cyanoarene-based fluorophores, such as 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), have been widely applied in photoredox catalysis and used as excellent metal-free alternatives to noble metal Ir- and Ru-based photocatalysts. However, all the reported photoredox reactions involving this chromophore family are based on harnessing the energy from a single visible light photon, with a limited range of redox potentials from -1.92 to +1.79 V vs SCE. Here, we document the unprecedented discovery that this family of fluorophores can undergo consecutive photoinduced electron transfer (ConPET) to achieve very high reduction potentials. One of the newly synthesized catalysts, 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile (3CzEPAIPN), possesses a long-lived (12.95 ns) excited radical anion form, 3CzEPAIPN?-*, which can be used to activate reductively recalcitrant aryl chlorides (Ered ≈ -1.9 to -2.9 V vs SCE) under mild conditions. The resultant aryl radicals can be engaged in synthetically valuable aromatic C-B, C-P, and C-C bond formation to furnish arylboronates, arylphosphonium salts, arylphosphonates, and spirocyclic cyclohexadienes.

Practical synthesis of phosphonium salts with orthoformates and their application as flame retardants in polycarbonate

An efficient and practical approach to phosphonium salts has been developed. By the reaction of phosphines and different acid sources with orthoformates in one-step operation, the process allowed rapid access to phosphonium salts with diverse counterions in high yield after the purification by recrystallization. The flame retardant performance in PC has also been examined by blending several phosphonium salts to PC respectively. Phosphonium phosphates showed excellent flame retardancy in PC with only 2 phr blending.

Quaternary phosphonium salt flame retardant and synthesis method and application thereof

The invention provides a quaternary phosphonium salt flame retardant and a synthesis method and application thereof, and the method comprises the following steps: by taking an acidic compound, ortho-formic acid trisubstituted ester and an organic phosphine compound III or IV as raw materials, carrying out a one-step reaction process to prepare the quaternary phosphonium salt flame retardant I or II. The flame retardant disclosed by the invention has good thermal stability and has an excellent flame-retardant effect when being applied to various polymers. The method is simple and convenient insynthesis operation, low in raw material price, mild in synthesis condition and high in yield. According to the synthesis method, introduction of halogen ions is avoided, and dozens of anions are successfully introduced. By adding a small amount of the flame retardant, the obtained PC flame-retardant composite material UL-94 can reach the V-0 grade.

A three phenyl methyl chloride [...] method for the preparation of

The invention discloses a preparation method of triphenylmethylphosphonium chloride. The triphenylmethylphosphonium chloride is prepared by using methanol as a solvent and triphenylphosphonium and methyl chloride as reactants. The reaction formula is as follows: (C6H5)3P+CH3Cl-->(C6H5)3CH3PCl. In the formula, the mol ratio of the triphenylphosphonium to the methyl chloride is 1:1-1:2. After the reaction, the process of reflux, distillation and recrystallization is carried out. By controlling the time, temperature, pressure and reactant mol ratio in the reaction process and carrying out the process of reflux, distillation and recrystallization after the reaction, the invention enhances the yield of the product triphenylmethylphosphonium chloride, and the product triphenylmethylphosphonium chloride has the advantages of fewer impurities and high purity (higher than 99%). Besides, the solvent used in the reaction process can be recycled, thereby saving the cost and being more environment-friendly.

A direct synthesis of vinylphosphonium salts from α-trimethylsilyl ylides and non-enolizable aldehydes

A direct synthesis of vinylphosphonium salts from α-trimethylsilyl ylides and non-enolizable aldehydes was reported. The vinylphosphonium salt was isolated in 90% yield and with high stereoselectivity favoring the (E)-olefin. High chemoselectivity observed favoring Peterson elimination over Wittig-type elimination and general stereoselectivity favoring (E)-vinylphosphonium salts require free-rotation about the central C-C bond of a betaine intermediate. The results show that the clean synthesis of the stable silylphosphonium iodide salt, subsequent generation of its yield derivative, and stoichiometric reaction with aldehydes at low temperature allows highly selective vinylphosphonium salt formation. It is also seen that the (E)-vinylphosphonium stereoselectivity is due to kinetic control involving Peterson syn-elimination from the erythro betaine.

Synthesis and Properties of Phosphabetaine Structures. I. Reactions of Triphenylphosphine and Triphenyl Phosphite with Unsaturated Carboxylic Acids and Their Derivatives

Reactions of triphenylphosphine and triphenyl phosphite with unsaturated carboxylic acids and their derivatives yield, depending on the nature of the reactants, phosphobetaine carboxylates, phosphonium salts, functionally substituted phosphonates, and als

Modified borohydride agents; Efficient reduction of azides with (1,4- diazabicyclo[2.2.2]octane) (tetrahydroborato)zinc complex [Zn(BH4)2(dabco)] and methyltriphenylphosphonium tetrahydroborate [MePh3P+BH-4]

(1,4-Diazabicyclo[2.2.2]octane)(tetrahydroborato)zinc complex and methyltriphenylphosphonium tetrahydroborate are stable modified borohydrides which are used for the efficient reduction of aryl, alkyl, and aroyl azides with excellent yields in THF or CH2Cl2 at room temperature or under reflux conditions.